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Journal articles on the topic 'Dioxolane ring'

Author: Grafiati

Published: 4 June 2021

Last updated: 14 February 2022

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1

Rjabovs, Vitalijs, Dmitrijs Stepanovs, and Maris Turks. "Crystal structure of 3-C-(N-benzyloxycarbonyl)aminomethyl-3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-allofuranose." Acta Crystallographica Section E Crystallographic Communications 71, no. 10 (September 26, 2015): 1212–15. http://dx.doi.org/10.1107/s2056989015017582.

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The title compound, C21H29NO7(1) [systematic name: benzyl ({(3aR,5S,6R,6aR)-5-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-yl}methyl)carbamate], consists of a substituted 2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxolane skeleton. The furanose ring adopts an envelope conformation close toC3-exo, where the C atom substituted by the benzyl carbamate group is the flap. The fused dioxolane ring also adopts an envelope conformation, as does the terminal dioxolane ring, with in each case an O atom as the flap. In the crystal, molecules are linked by N—H...O and C–H...O hydrogen bonds, forming chains propagating along theb-axis direction.

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2

Kavitha, Channappa N., Jerry P. Jasinski, Brian J. Anderson, H. S. Yathirajan, and Manpreet Kaur. "Bis{4-[(1,3-benzodioxol-5-yl)methyl]piperazin-1-yl}methane." Acta Crystallographica Section E Structure Reports Online 69, no. 11 (October 19, 2013): o1669. http://dx.doi.org/10.1107/s1600536813028109.

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In the title compound, C25H32N4O4, both piperazine rings adopt a chair conformation. One of dioxolane ring systems is essentially planar [dihedral angle = 0.9 (2)°] while the other adopts a slightly disordered envelope conformation, the mean plane of the dioxolane ring being twisted by 3.6 (2)° from that of the benzene ring. The dihedral angle between the benzene rings is 69.9 (5)°. No classical hydrogen bonds were observed.

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3

Kirchner, Richard M., Peter W. R. Corfield, Michelle Annabi, John Regan, Kevin Speina, Anthony DiProperzio, James A. Ciaccio, and Joseph F. Capitani. "Crystal structure of 2α-(1,1-diphenylethyl)-4-methyl-4α,5α-diphenyl-1,3-dioxolane: the result of a non-acid pinacol rearrangement." Acta Crystallographica Section E Crystallographic Communications 71, no. 11 (October 3, 2015): 1278–82. http://dx.doi.org/10.1107/s2056989015017752.

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The title compound, C30H28O2, was obtained during recrystallization of (±)-1,2-diphenyl-1,2-propanediol in 1-butanol, from an unexpected non-acid-catalyzed pinacol rearrangement followed by acetal formation of the newly formed aldehyde with the diol. The tri-substituted dioxolane ring has a twist conformation on the C—O bond opposite the methyl-substituted C atom. There is an intramolecular C—H...π interaction present involving one of the diphenylethyl rings and an H atom of the phenyl ring in position 4 of the dioxolane ring. In the crystal, molecules are linked by weak C—H...O hydrogen bonds, forming chains along [001]. The chains are linked by a second C—H...π interaction, forming sheets parallel to thebcplane.

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4

Semjonovs, Nikita, Vitalijs Rjabovs, Dmitrijs Stepanovs, and Maris Turks. "Crystal structure of 3-O-benzyl-4(R)-C-(1-benzyl-1H-1,2,3-triazol-4-yl)-1,2-O-isopropylidene-α-D-erythrofuranose." Acta Crystallographica Section E Crystallographic Communications 71, no. 12 (November 28, 2015): 1542–44. http://dx.doi.org/10.1107/s2056989015022434.

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The title compound, C23H25N3O4, {systematic name: 1-benzyl-4-[(3aR,5R,6R,6aR)-6-benzyloxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-1H-1,2,3-triazole}, consists of a substituted 2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole. The furanose ring adopts an envelope conformation close toC3-exo, where the C atom substituted by the benzyloxy group is the flap. The fused dioxolane ring also adopts an envelope conformation, with the methylene C atom as the flap. In the crystal, molecules are linked by weak C—H...O hydrogen bonds, forming zigzag chains along [010].

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5

Jahangiri, Amita, Ola F. Wendt, and Daniel Strand. "(6R*,10R*)-Dimethyl 1,4-dioxaspiro[4.5]decane-6,10-dicarboxylate." Acta Crystallographica Section E Structure Reports Online 69, no. 2 (January 19, 2013): o265. http://dx.doi.org/10.1107/s160053681300161x.

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The title compound, C12H18O6, is in the usual chair conformation with the two ester functions in a 1,3-transorientation. With a value of 1.439 (2) Å, the pseudo-axial C—O bond of the 1,3-dioxolane ring is slightly longer than the corresponding equatorial C—O bond of 1.424 (3) Å. The O—C—O angle of the dioxolane ring is 106.25 (17)°.

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6

Oishi, Takeshi, Keisuke Fukaya, Yu Yamaguchi, Tomoya Sugai, Ami Watanabe, Takaaki Sato, and Noritaka Chida. "Crystal structures of (±)-(1SR,5SR,6SR,7SR,10SR,11SR,13RS,14SR)-13-hydroxy-7-methoxymethoxy-11,15,18,18-tetramethyl-3-oxo-2,4-dioxatetracyclo[12.3.1.01,5.06,11]octadec-15-en-10-yl benzoate, its 13-epimer and 13-one derivative." Acta Crystallographica Section E Crystallographic Communications 71, no. 5 (April 9, 2015): 466–72. http://dx.doi.org/10.1107/s2056989015006854.

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The title compounds, C29H38O8·0.25C5H12, (A), C29H38O8, (B), and C29H36O8, (C), are tetracyclic benzoates possessing a taxane skeleton with a fused dioxolane ring as the core structure. In the asymmetric unit of (A), there are two independent benzoate molecules (A and A′) and a half molecule of solvent pentane disordered about an inversion center. The molecular conformations of (A), (B) and (C) are similar except for the flexible methoxymethoxy group. The cyclohexane, cyclohexene and central cyclooctane rings adopt chair, half-chair and chair–chair (extended crown) forms, respectively. The dioxolane rings are essentially planar, while the dioxolane ring of A′ is slightly twisted from the mean plane. In the crystal of (A), intermolecular O—H...O, C—H...O and C—H...π interactions link the independent benzoates alternately, forming a chain structure. In the crystals of (B) and (C), molecules are linked through O—H...O and C—H...π interactions, and C—H...O hydrogen bonds, respectively, into similar chains. Further, weak intermolecular C—H...O interactions connect the chains into a three-dimensional network in (A) and a sheet in (B), whereas no other interactions are observed for (C).

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7

Xu, Yuechao, Mitchell R. Perry, Stefan A. Cairns, and Michael P. Shaver. "Understanding the ring-opening polymerisation of dioxolanones." Polymer Chemistry 10, no. 23 (2019): 3048–54. http://dx.doi.org/10.1039/c8py01695j.

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8

McClelland, Robert A., and Claude Moreau. "Reversible ring opening in the hydrolysis of spiro ortho esters." Canadian Journal of Chemistry 63, no. 10 (October 1, 1985): 2673–78. http://dx.doi.org/10.1139/v85-444.

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Hydrolysis kinetics are reported for four spiro ortho esters: 3,4-dihydro-6-methoxy-1H-2-benzopyran-1-spiro-2′-1′,3′-dioxolane (13), its 1′,3′-dioxane analog (14), and the 6-unsubstituted versions of each (11 and 12). For comparison, also included are the diethoxy analogs: 1,1-diethoxy-3,4-dihydro-6-methoxy-1H-2-benzopyran (10) and the 6-unsubstituted compound (9). Product analysis implicates an initial opening of the dioxolane or dioxane ring in the spiro ortho esters, as expected on the basis of stereoelectronic considerations. The intermediate dialkoxycarbocations can be observed in HCl solutions. A detailed analysis has been carried out for the 6-methoxy systems to provide the rate constants k1, the second-order rate constant for H+-catalyzed formation of the cation from the ortho ester, k2, the first-order rate constant for water addition to the cation, and k−1, the first-order rate constant for ring closing of the cation to reform the ortho ester. The two spiro ortho esters are shown in this analysis to undergo reversible ring opening in their hydrolysis, in that values of k−1, are greater than k2. The differences, however, are not large, k−1/k2 being 1.2 (dioxolane, 13) and 3.8 (dioxane, 14). Comparison with the diethoxy ortho ester also reveals that the ring opening process (k1, rate constants) is inherently more difficult with the dioxolane, although not with the dioxane. An argument involving lone pair orientation is advanced to explain this.

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9

Sherif, M. H., E. Klemm, W. Günther, and D. Stadermann. "Photopolymerization of Exo-Methylene-1,3-Dioxolane with Bisphenol-A-Diglycidylether and Methyl Methacrylate Using Photoinitiators." Polymers and Polymer Composites 9, no. 5 (July 2001): 327–31. http://dx.doi.org/10.1177/096739110100900503.

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The copolymerization of 2-exo-methylene-4-phenyl, 3-dioxolane with bisphenol-A-diglycidylether and methyl methacrylate using a cationic and a radical initiator is described. The structure of the polymers is elucidated by NMR and IR spectroscopy. Using a cationic photoinitiator the dioxolane structure is maintained in the copolymer and remaining oxirane structures from the bisphenol-A-diglycidylether can be proved. Surprisingly, no complete ring-opening of the dioxolane takes place in the presence of a radical initiator leading to statistical copolymers with methyl methacrylate.

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10

Raskil’dina, Gul’nara Z., Evgeniya A. Yakovenko, Luisa M. M. Mryasova, and Simon S. Zlotskii. "SYNTHESIS AND HERBICID ACTIVITY OF ARYLOXYACETIC ACIDS AND AMIDES OF ARYLOXY ACETIC ACIDS CONTAINING CYCLOACETAL FRAGMENT." IZVESTIYA VYSSHIKH UCHEBNYKH ZAVEDENIY KHIMIYA KHIMICHESKAYA TEKHNOLOGIYA 62, no. 1 (December 30, 2018): 91–97. http://dx.doi.org/10.6060/ivkkt.20196201.5753.

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The herbicidal activity of esters and amides based on commercially available phenoxy chlorides and 2,4-dichlorophenoxyacetic acids was studied. Esters of 2,2-methyl-4-hydroxymethyl-1,3-dioxolane, 5-ethyl-5-hydroxymethyl-1,3-dioxane and 1,3-dioxolan-4-ylmethanol and 1,3-dioxane-5 -ol (glycerin formulas), as well as amides containing gem-dichlorocyclopropane and 1,3-dioxolane fragments were obtained. The acid chlorides, 1,3-dioxacycloalkanes and secondary amines were prepared according to standard basic methods. Esters and amides were synthesized from these starting compounds in a short time and with a quantitative yield (more than 90%). As a result of the synthesis of a mixture of 1,3-dioxolan-4-ylmethyl phenylacetate and 1,3-dioxan-5-yl phenylacetate, the content of the 5-ring cyclic derivative over the 6-chain structure was predominant, which is obviously associated with greater activity in the esterification reaction of primary alcohol than secondary. The screening results showed that the activity relative to wheat of the 1,3-dioxalane ester of 2,4-dichlorophenoxyacetic acid is superior to the Octagon-Extra standard. With respect to peas, derivatives of 2,4-dichlorophenoxyacetic acid and 2,2-dimethyl-4-hydroxymethyl-1,3-dioxolane are close to the standard for inhibition of shoot mass. The results of N-benzyl-N-[(2,2-dichlorocyclopropyl) methyl] -2-phenoxyacetamide and N-[(2,2-dichlorocyclopropyl) methyl]-N-(1,3-dioxolan-4-ylmethyl)-2-phenoxyacetamide with respect to peas and wheat also showed a marked herbicidal effect, close in value to the reference one. The test results of synthesized benzamides on wheat showed that, at a concentration of 100 mg/l, the compounds act approximately the same as the reference preparation at a dose of 50 mg/l. The obtained results prove the prospects of creating herbicidal preparations based on phenoxy- chlorides and 2,4-dichlorophenoxyacetic acids containing 1,3-dioxacycloalkane fragments. Therefore, these objects are very attractive for further study and synthesis of biologically active compounds containing the above pharmacophore groups.

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11

Liu, Ya-Ling, Pei Zou, Hao Wu, Min-Hao Xie, and Shi-Neng Luo. "3,4,6-Tri-O-acetyl-1,2-O-[1-(exo-ethoxy)ethylidene]-β-D-mannopyranose 0.11-hydrate." Acta Crystallographica Section C Crystal Structure Communications 68, no. 9 (August 1, 2012): o338—o340. http://dx.doi.org/10.1107/s0108270112032076.

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The title compound, C16H24O10·0.11H2O, is a key intermediate in the synthesis of 2-deoxy-2-[18F]fluoro-D-glucose (18F-FDG), which is the most widely used molecular-imaging probe for positron emission tomography (PET). The crystal structure has two independent molecules (AandB) in the asymmetric unit, with closely comparable geometries. The pyranose ring adopts a4C1conformation [Cremer–Pople puckering parameters:Q= 0.553 (2) Å, θ = 16.2 (2)° and ϕ = 290.4 (8)° for moleculeA, andQ= 0.529 (2) Å, θ =15.3 (3)° and ϕ = 268.2 (9)° for moleculeB], and the dioxolane ring adopts an envelope conformation. The chiral centre in the dioxolane ring, introduced during the synthesis of the compound, has anRconfiguration, with the ethoxy groupexoto the mannopyranose ring. The asymmetric unit also contains one water molecule with a refined site-occupancy factor of 0.222 (8), which bridges between moleculesAandB viaO—H...O hydrogen bonds.

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12

Li, Jian, Jia Qi Ma, Wei Min Mo, and Zhen Lu Shen. "7,7-[Ethane-1,2-diylbis(oxy)]-2-[hydroxy(phenyl)methyl]bicyclo[3.3.1]nonan-3-one." Acta Crystallographica Section E Structure Reports Online 70, no. 6 (May 17, 2014): o665. http://dx.doi.org/10.1107/s1600536814009040.

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In the title compound, C18H22O4, the cyclohexane and cyclohexanone rings adopt normal chair and half-chair conformations, respectively. The dioxolane ring is almost planar, with an r.m.s. deviation of 0.094 (3) Å. In the crystal, molecules are connected by O—H...O hydrogen bonds, forming 21helical chains along thea-axis direction. The chains are further connected by C—H...O hydrogen bonds.

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13

Bortoluzzi, Adailton J., Gustavo P. Silveira, and Marcus M. Sá. "Crystal structure of 5-O-benzoyl-2,3-O-isopropylidene-D-ribono-1,4-lactone." Acta Crystallographica Section E Crystallographic Communications 73, no. 3 (February 17, 2017): 407–9. http://dx.doi.org/10.1107/s2056989017002043.

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In the title compound, C15H16O6, obtained from the acylation reaction between 2,3-O-isopropylidene-D-ribono-1,4-lactone and benzoyl chloride, the known absolute configuration for the lactone moiety of the ester substituent has been confirmed. The five-membered rings of the bicyclic lactone–dioxolane moiety both show envelope conformations and form a dihedral angle of 19.82 (7)° between the lactone ring and the benzene ring. In the crystal, molecules of the acylated sugar are linked by very weak intermolecular C—H...O interactions, forming a three-dimensional network.

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14

Giles, Robin G. F., Ivan R. Green, and Shuk-Hui Li. "Stereoselective Isomerizations of 4-(2´-Chloro-3´-methoxyphenyl)-2,5-dimethyl-1,3-dioxolanes: Stereochemistry and Conformation of the Product 2-Benzopyrans." Australian Journal of Chemistry 58, no. 8 (2005): 565. http://dx.doi.org/10.1071/ch05120.

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Stereoselective isomerization of rel-(2R,4S,5R)-4-(2′-chloro-3′-methoxyphenyl)-2,5-dimethyl-1,3-dioxolane 5 with titanium(iv) chloride afforded solely rel-(1R,3R,4S)-5-chloro-4-hydroxy-6-methoxy-1,3-dimethyl-2-benzopyran 17 in high yield in which the conformation adopted by the dihydropyran ring minimized peri-interactions through stereochemistries that were axial for the C-3 methyl, pseudoaxial for the C-4 hydroxy and pseudoequatorial for the C-1 methyl groups. Similar isomerization of the individual rel-(2S,4R,5R)- and rel-(2R,4R,5R)-diastereoisomeric dioxolanes 6 and 7 gave solely the corresponding rel-(1S,3R,4R)-2-benzopyran 25 in which the orientations of the substituents at C-3, C-4 and C-1 were equatorial, pseudoaxial and pseudoequatorial respectively. These observations differed significantly from those previously made for the related isomerizations of the corresponding 4-(2′-chloro-5′-methoxyphenyl)-2,5-dimethyl-1,3-dioxolanes.

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15

Rjabovs, Vitālijs, Anatoly Mishnev, Glebs Kiselovs, and Māris Turks. "{(3aR,5S,6R,6aR)-5-[(R)-1,2-Dihydroxyethyl]-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-yl}methyl methanesulfonate." Acta Crystallographica Section E Structure Reports Online 70, no. 5 (April 5, 2014): o524—o525. http://dx.doi.org/10.1107/s1600536814007387.

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In the title compound, C11H20O8S, the furanose ring has a pseudorotation phase angle equal to 31.3° and assumes a3T4conformation, with deviations of 0.297 (4) and −0.152 (4) Å for the corresponding C atoms. The dioxolane ring adopts an envelope conformation. One of the O atoms is at the flap and deviates from the least-squares plane formed by the other four ring atoms by 0.405 (2) Å. The dihedral angle between the planar fragments of the rings is 63.53 (8)°. In the crystal, molecules are associated into sheets perpendiculer to thebaxis by means of O—H...O hydrogen bonds. A few weak C—H...O interactions are also observed.

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16

Jagadeesan, G., K. Sethusankar, R. Prasanna, and R. Raghunathan. "Ethyl 7′-(6-benzyloxy-2,2-dimethyltetrahydrofuro[3,2-d][1,3]dioxol-5-yl)-2-oxo-5′,6′,7′,7a'-tetrahydro-1′H,2H-spiro[acenaphthylene-1,5′-pyrrolo[1,2-c][1,3]thiazole]-6′-carboxylate." Acta Crystallographica Section E Structure Reports Online 68, no. 8 (July 21, 2012): o2505—o2506. http://dx.doi.org/10.1107/s1600536812032291.

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In the title compound, C34H35NO7S, the acenaphthylene unit is essentially planar (r.m.s. deviation = 0.0335 Å). The pyrrolothiazole ring system is folded about the bridging N—C bond; the thiazolidine and pyrrolidine rings adopt S- and C-envelope conformations, respectively, with a `butterfly' angle between the mean planes of 51.38 (10)°. The dioxolane and tetrahydrofuran rings adopt O- and a C-envelope conformations, respectively, with a `butterfly' angle between the mean planes of 57.12 (10)°. Two C atoms are each disordered over two positions with site-occupancy factors of 0.450 (7) and 0.550 (7). The crystal packing is stabilized by C—H...O interactions, generating anR22(14) graph-set ring motif.

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17

Coenen, Anna M. J., Jules A. W. Harings, Samaneh Ghazanfari, Stefan Jockenhoevel, and Katrien V. Bernaerts. "Formation of cyclic structures in the cationic ring-opening polymerization of 1,3-dioxolane." RSC Advances 10, no. 16 (2020): 9623–32. http://dx.doi.org/10.1039/d0ra00904k.

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Elucidating the mechanism of the cationic ring-opening polymerization of dioxolane using gel permeation chromatography, matrix assisted laser desorption/ionization time of flight mass spectrometry and ³¹P NMR.

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18

Kost, Bartłomiej, and Malgorzata Basko. "Synthesis and properties of l-lactide/1,3-dioxolane copolymers: preparation of polyesters with enhanced acid sensitivity." Polymer Chemistry 12, no. 17 (2021): 2551–62. http://dx.doi.org/10.1039/d1py00358e.

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19

Oishi, Takeshi, Keisuke Fukaya, Yu Yamaguchi, Tomoya Sugai, Ami Watanabe, Takaaki Sato, and Noritaka Chida. "Crystal structure of (±)-(1SR,5SR,6SR,7SR,10SR,11SR,13SR)-13-benzyloxy-7-methoxymethoxy-11,15,18,18-tetramethyl-3-oxo-2,4-dioxatetracyclo[12.3.1.01,5.06,11]octadeca-14,16-dien-10-yl benzoate." Acta Crystallographica Section E Crystallographic Communications 71, no. 5 (April 18, 2015): 490–93. http://dx.doi.org/10.1107/s2056989015007136.

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In the title compound, C36H42O8, the dioxolane ring adopts a twist conformation; the two adjacent C atoms deviate alternately from the mean plane of other atoms by −0.287 (5) and 0.174 (5) Å. The cyclohexane, cyclohexadiene and central cyclooctane rings show chair, half-chair and boat–chair forms, respectively. As a result of the strained ring system, the tetrasubsituted olefin in the cyclohexadiene is skewed from an ideal planar structure. In the crystal, C—H...O hydrogen bonds connect the molecules into a sheet parallel to (100). The sheets are further linked by other weak C—H...O and C—H...π interactions, forming a three-dimensional network.

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20

Tiritiris, Ioannis, Stefan Tussetschläger, and Willi Kantlehner. "Crystal structure of 1,2,3,4-di-O-methylene-α-D-galactopyranose." Acta Crystallographica Section E Crystallographic Communications 71, no. 12 (November 21, 2015): o961—o962. http://dx.doi.org/10.1107/s2056989015021854.

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The title compound, C8H12O6, was synthesized by deacetylation of 6-acetyl-1,2,3,4-di-O-methylene-α-D-galactose with sodium methoxide. The central part of the molecule consists of a six-membered C5O pyranose ring with a twist-boat conformation. Both fused dioxolane rings adopt an envelope conformation with C and O atoms as the flap. In the crystal, O—H...O and C—H...O hydrogen bonds are present between adjacent molecules, generating a three-dimensional network.

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21

Oishi, Takeshi, Koki Ishii, Mizuki Ishibashi, Takaaki Sato, and Noritaka Chida. "Crystal structure of (–)-(R,E)-3-(1,3-benzodioxol-5-yl)-5-[(4S,5R)-5-hydroxymethyl-2,2-dimethyl-1,3-dioxolan-4-yl]-N,N-dimethylpent-4-enamide." Acta Crystallographica Section E Crystallographic Communications 74, no. 6 (May 18, 2018): 825–28. http://dx.doi.org/10.1107/s2056989018007132.

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In the title compound, C20H27NO6, the amide moiety is essentially planar, with a maximum deviation of 0.073 (3) Å, and one of the N-methyl groups shows rotational disorder. The five-membered 1,3-dioxolane ring adopts an envelope form, with the C atom bonded to the olefin side chain as the flap, which deviates from the mean plane through the other four atoms by 0.564 (7) Å. The 1,3-dioxole ring fused to the benzene ring adopts a flattened envelope form, with the C atom between the two O atoms as the flap, which deviates from the mean plane through the other four atoms by 0.215 (7) Å. The C—C=C—C olefin moiety is essentially planar and makes a dihedral angle of 87.1 (3)° with the benzene ring. An intramolecular O—H...O hydrogen bond supports the molecular conformation, enclosing an S(11) graph-set motif. In the crystal, intermolecular C—H...O hydrogen bonding links the molecules into a tape running along the b axis. Furthermore, other weak C—H...O hydrogen bonds and a C—H...π interaction connect the tapes into a sheet structure parallel to (100).

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22

Memarian, Hamid R., and Farzad Nikpour. "Photocatalytic Ring Opening of α-Epoxyketones: 1,3-Dioxolane Formation." Monatshefte für Chemie / Chemical Monthly 133, no. 7 (July 2002): 1045–53. http://dx.doi.org/10.1007/s007060200073.

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23

Xie, Xue-Qun, Chun-Long Yang, Jin-Xiang Luo, and Qian-Jin Li. "1-{[1-(2,4-Dichlorophenyl)-1,3-dioxolan-2-yl]methyl}-1H-1,2,4-triazole." Acta Crystallographica Section E Structure Reports Online 62, no. 7 (June 16, 2006): o2858—o2859. http://dx.doi.org/10.1107/s1600536806021386.

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In the title compound, C12H11Cl2N3O2, also referred to as azaconazole, the five-membered 1,3-dioxolane ring assumes an envelope conformation. In the crystal packing, the molecules are linked into an extended three-dimensional network by weak C—H...O interactions.

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24

Wood, Adam, Paul V. Bernhardt, Ian van Altena, and Michela I. Simone. "Crystal structure of 6-azido-6-deoxy-1,2-O-isopropylidene-α-D-glucofuranose." Acta Crystallographica Section E Crystallographic Communications 76, no. 10 (September 18, 2020): 1653–56. http://dx.doi.org/10.1107/s2056989020012438.

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Short syntheses to high Fsp 3 index natural-product analogues such as iminosugars are of paramount importance in the investigation of their biological activities and reducing the use of protecting groups is an advantageous synthetic strategy. An isopropylidene group was employed towards the synthesis of seven-membered ring iminosugars and the title compound, C9H15N3O5, was crystallized as an intermediate, in which the THF ring is twisted and the dioxolane ring adopts an envelope conformation: the dihedral angle between the rings is 67.50 (13)°. In the crystal, the hydroxyl groups participate in O—H...(O,O) and O—H...N hydrogen-bonding interactions, which generate chains of molecules propagating parallel to the a-axis direction. There is a notable non-classical C—H...O hydrogen bond, which cross-links the [100] chains into (001) sheets.

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25

Lv, Chun-Lei, Jian-Hui Chen, Yu-Zhe Zhang, Ding-Qiang Lu, and Ping-Kai OuYang. "(4R*,5R*)-Diethyl 2-(4-nitrophenyl)-1,3-dioxolane-4,5-dicarboxylate." Acta Crystallographica Section E Structure Reports Online 68, no. 4 (March 21, 2012): o1128. http://dx.doi.org/10.1107/s160053681201118x.

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In the title compound, C15H17NO8, the nitro group is essentially coplanar with the aromatic ring [dihedral angle = 6.4 (3) Å]. The five-membered ring has a twist conformation. In the crystal, C—H...O interactions link the molecules into a helical chain propagating along [010].

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26

Memarian, Hamid Reza, and Sakineh Zare. "Diastereoselective 1,3-Dioxolane Formation by Photocatalytic Ring Opening of α-Epoxyketones." Zeitschrift für Naturforschung B 68, no. 7 (July 1, 2013): 811–17. http://dx.doi.org/10.5560/znb.2013-3051.

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Photocatalytic ring opening of α-epoxyketones by 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) in acetone resulted in the diastereoselective formation of 1,3-dioxolanes through Cα-O bond cleavage. The facility of the ring opening is influenced by the nature and the location of the additional substituent on the a-epoxyketones.

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27

İlter, Zülfiye, Mehmet Çoşkun, İbrahim Erol, Arzu Ünal, and Misir Ahmedzade. "Thermal behaviour of some polymethacrylates with a 1,3-dioxolane ring." Polymer Degradation and Stability 75, no. 3 (January 2002): 501–8. http://dx.doi.org/10.1016/s0141-3910(01)00253-1.

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28

Oishi, Takeshi, Hiroaki Yamamoto, Tomoya Sugai, Keisuke Fukaya, Yu Yamaguchi, Ami Watanabe, Takaaki Sato, and Noritaka Chida. "Crystal structure of (±)-(7RS,8SR)-7-methyl-1,4-dioxaspiro[4.5]decane-7,8-diol." Acta Crystallographica Section E Crystallographic Communications 71, no. 10 (September 17, 2015): 1181–84. http://dx.doi.org/10.1107/s2056989015016783.

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In the title compound, C9H16O4, the five-membered dioxolane ring adopts a twist conformation; two adjacent C atoms deviate alternately from the mean plane of other atoms by −0.297 (4) and 0.288 (4) Å. The spiro-fused cyclohexane ring shows a chair form. The hydroxy group substituted in an axial position makes an intramolecular O—H...O hydrogen bond with one of the O atoms in the cyclic ether, forming anS(6) ring motif. In the crystal, the O—H...O hydrogen bond involving the equatorial hydroxy group connects the molecules into a zigzag chain with aC(5) motif running along thecaxis.

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29

Oishi, Takeshi, Yuu Yamaguchi, Keisuke Fukaya, Tomoya Sugai, Ami Watanabe, Takaaki Sato, and Noritaka Chida. "Crystal structure of (±)-(4RS,5RS,7SR)-4-[(1RS,2RS,3RS,6RS)-3-benzoyloxy-2-(2-hydroxyethyl)-6-methoxymethoxy-2-methylcyclohexyl]-8,10,10-trimethyl-2-oxo-1,3-dioxaspiro[4.5]dec-8-en-7-yl benzoate benzene monosolvate." Acta Crystallographica Section E Crystallographic Communications 71, no. 1 (January 1, 2015): 8–11. http://dx.doi.org/10.1107/s2056989014026048.

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In the title compound, C36H44O10·C6H6, the dioxolane ring adopts an envelope conformation with the C atom bonded to the H atom as the flap, while the cyclohexene and cyclohexane rings are in half-chair and chair conformations, respectively. In the crystal, a pair of O—H...O hydrogen bonds with anR22(26) graph-set motif connect the benzoate molecules into an inversion dimer. The dimers are linked by a weak C—H...O interaction into a tape structure along [01-1]. The benzene molecule links the tapes through C—H...O and C—H...π interactions, forming a sheet parallel to (100).

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30

Geng, Wei Wei, Shou Zhi Pu, and Shi Qiang Cui. "Synthesis and Properties of a Novel Unsymmetrical Diarylethene with Five and Six Ring Aryls." Advanced Materials Research 490-495 (March 2012): 3676–80. http://dx.doi.org/10.4028/www.scientific.net/amr.490-495.3676.

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A novel photochromic diarylethene with thiophene and benzene compound, 1-{[2-methyl-5-(1, 3-dioxolane)-3-thienyl]}-2-(2-cyanophenyl)perfluorocyclopentene(1a) has been synthesized. Its photochemical properties, including photochromic behavior and fluorescent features, have been investigated in detail. The compound showed good photochromism both in solution and in PMMA. The diarylethene exhibited a fluorescence switches along with the photochromism from open-ring isomers to closed-ring isomers. When irradiated by UV light, the photocyclization reaction was occurred and the emission intensity of the diarylethene decreased significantly, due to producing the non-fluorescence closed-ring isomers. The back irradiation by appropriate wavelength visible light regenerated its open-ring isomers and recovered the original emission intensity.

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31

Mehta, Goverdhan, and Tabrez Babu Khan. "(1′S,6′S,8′S,9′R)-9′-Bromo-12′-oxaspiro[1,3-dioxolane-2,4′-tricyclo[6.3.1.01,6]dodecane]." Acta Crystallographica Section E Structure Reports Online 68, no. 8 (July 10, 2012): o2411—o2412. http://dx.doi.org/10.1107/s1600536812029777.

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In an endeavor directed towards the construction of the oxabicyclic[3.2.1]octane segment present in the bioactive natural products of cortistatins and icetexanes genre, the title compound, C13H19BrO3, was synthesized from (4aR,9aS)-1,3,4,4a,5,6,9,9a-octahydrospiro[benzo[7]annulene-2,2′-[1,3]dioxolane]-4a-olviaa transannular bromo-etherification protocol. The six-membered ring adopts a twist-boat conformation, while the fused cycloheptane ring adopts a chair conformation. The crystal packing is effected through two distinct intermolecular C—H...O hydrogen-bond patterns and molecules are arranged to define an interesting motif along thebaxis.

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32

Geng, Wei Wei, Cong Bin Fan, and Shou Zhi Pu. "Synthesis and Properties of a Novel Material Chemistry Unsymmetrical Material, Diarylethene with Cyano." Applied Mechanics and Materials 164 (April 2012): 150–53. http://dx.doi.org/10.4028/www.scientific.net/amm.164.150.

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A unsymmetrical photochromic diarylethene, 1-{[2-methyl-5-(1,3-dioxolane)-3-thienyl]} -2-[2-methyl-5-(4-cyanophenyl)-3-thienyl]perﬂuorocyclopentene(1a),was synthesized, and its optoelectronic properties were also investigated in detail. The results showed that this compound exhibited reversible photochromism, changing from colorless to blue violet after irradiation with UV light both in solution and in PMMA amorphous film.The diarylethene exhibited a fluorescence switches along with the photochromism from open-ring isomers to closed-ring isomers. When irradiated by UV light, the photocyclization reaction was occurred and the emission intensity of the diarylethene decreased significantly, due to producing the non-fluorescence closed-ring isomers. The back irradiation by appropriate wavelength visible light regenerated its open-ring isomers and recovered the original emission intensity

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33

MASUYAMA, Araki, Daisuke ONO, Akira YAMAMOTO, Toshiyuki KIDA, Yohji NAKATSUJI, and Tokuji TAKEDA. "Unique Betaine Types of Surfactants Bearing a 1, 3-Dioxolane Ring." Journal of Japan Oil Chemists' Society 44, no. 6 (1995): 446–50. http://dx.doi.org/10.5650/jos1956.44.446.

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34

Park, Jaekyeung, Tsutomu Yokozawa, and Takeshi Endo. "Cationic ring-opening polymerization of 2-isopropenyl-4-methylene-1,3-dioxolane." Journal of Polymer Science Part A: Polymer Chemistry 31, no. 5 (April 1993): 1141–45. http://dx.doi.org/10.1002/pola.1993.080310507.

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35

Memarian, Hamid R., and Farzad Nikpour. "ChemInform Abstract: Photocatalytic Ring Opening of α-Epoxyketones: 1,3-Dioxolane Formation." ChemInform 33, no. 41 (May 19, 2010): no. http://dx.doi.org/10.1002/chin.200241119.

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36

Pan, Xiao-liang, Yi-xuan Zhou, Wei Liu, Jing-yao Liu, and Hai Dong. "Stereoelectronic control of cleavage of dioxolane five-membered ring on carbohydrates." Chemical Research in Chinese Universities 29, no. 3 (April 30, 2013): 551–55. http://dx.doi.org/10.1007/s40242-013-2293-6.

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37

Delplace, Vianney, Elise Guégain, Simon Harrisson, Didier Gigmes, Yohann Guillaneuf, and Julien Nicolas. "A ring to rule them all: a cyclic ketene acetal comonomer controls the nitroxide-mediated polymerization of methacrylates and confers tunable degradability." Chemical Communications 51, no. 64 (2015): 12847–50. http://dx.doi.org/10.1039/c5cc04610f.

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2 Methylene-4-phenyl-1,3-dioxolane (MPDL) was used as a controlling comonomer in NMP with oligo(ethylene glycol) methyl ether methacrylate (MeOEGMA) to prepare well-defined and degradable PEG-based P(MeOEGMA-co-MPDL) copolymers.

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38

Aben, R. W. M., and J. W. Scheeren. "Synthesis of 2-(2-alkoxyethylidene)-1,3-dioxolanes by using the 1,3-dioxolane ring as a double bond directing group." Tetrahedron Letters 29, no. 29 (January 1988): 3597–98. http://dx.doi.org/10.1016/0040-4039(88)85303-6.

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39

Silva, Luiz Everson da, Carla Regina Andrighetti-Fröhner, Ricardo José Nunes, Cláudia Maria Oliveira Simões, and Sabine Foro. "(1,3-Benzodioxol-5-ylmethyl)ammonium 2-methoxy-5-[(1E)-3-oxo-3-phenylprop-1-en-1-yl]bezenesulfonate monohydrate." Acta Crystallographica Section E Structure Reports Online 62, no. 7 (June 14, 2006): o2785—o2787. http://dx.doi.org/10.1107/s1600536806021076.

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The reaction of a chalcone derivative and an arylmethylamine yields the title organic salt, C8H10NO2 +·C16H13O5S−·H2O. The 1,3-dioxolane ring exhibits an envelope conformation. The C—C—C—C torsion angle of 16.7 (7)° between the 2-methoxy-5-vinylbenzenesulfonate unit and the phenyl ring indicates the non-planarity of the system. The polar heads of the anion and cation are connected by two bifurcated N—H...O hydrogen bonds. The water molecule completes hydrophilic interactions by N—H...O hydrogen bonds with the cation and O—H...O bonds with the anion along the a axis.

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40

Wang, Ren Jie, Gang Liu, Shi Qiang Cui, and Hong Ying Xia. "Synthesis, Photochromic Properties and Application in Optical Memory of a Diarylethene Based on Pyrrole Ring." Advanced Materials Research 399-401 (November 2011): 1107–10. http://dx.doi.org/10.4028/www.scientific.net/amr.399-401.1107.

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A new unsymmetrical photochromic diarylethene compound, 1-[(2-methyl-5-(4-dioxolane-phenyl)-3-thienyl)]-2-(5-cyano-1,5-dimethyl-4-pyrryl)perfluorocyclopentene (1o), was synthesized and its photochemical, fluorescence properties were investigated in detail both in solution and PMMA amorphous film. The results showed that the compound exhibited remarkable photochromism, changing from colorless to violet after irradiation with 297 nm UV light. Finally, using this diarylethene as recording medium, polarization optical recording was carried out successfully.

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41

Sekimata, Katsuhiko, Sun-Young Han, Koichi Yoneyama, Yasutomo Takeuchi, Shigeo Yoshida, and Tadao Asami. "A Specific and Potent Inhibitor of Brassinosteroid Biosynthesis Possessing a Dioxolane Ring." Journal of Agricultural and Food Chemistry 50, no. 12 (June 2002): 3486–90. http://dx.doi.org/10.1021/jf011716w.

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42

Peng, Chi-Chi, Wei Shi, Justin D. Lutz, Kent L. Kunze, Jun O. Liu, Wendel L. Nelson, and Nina Isoherranen. "Stereospecific Metabolism of Itraconazole by CYP3A4: Dioxolane Ring Scission of Azole Antifungals." Drug Metabolism and Disposition 40, no. 3 (November 21, 2011): 426–35. http://dx.doi.org/10.1124/dmd.111.042739.

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43

Park, Jaekyeung, Wonmun Choi, Nobuhiro Kihara, and Takeshi Endo. "Regioselective cationic ring-opening polymerization of 4-methylene-2-styryl-1,3-dioxolane." Journal of Polymer Science Part A: Polymer Chemistry 32, no. 5 (April 15, 1994): 983–85. http://dx.doi.org/10.1002/pola.1994.080320520.

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44

Kim, Tae-Mi, Youhyuk Kim, and Myoung-Seon Gong. "Ring-opening polymerization of 4-methylene-1,3-dioxolane derivatives with tungsten hexachloride." Macromolecular Rapid Communications 15, no. 8 (August 1994): 639–45. http://dx.doi.org/10.1002/marc.1994.030150804.

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45

Oishi, Takeshi, Mayu Kidena, Tomoya Sugai, Takaaki Sato, and Noritaka Chida. "Crystal structure of (–)-methyl (R,E)-4-[(2R,4R)-2-amino-2-trichloromethyl-1,3-dioxolan-4-yl]-4-hydroxy-2-methylbut-2-enoate." Acta Crystallographica Section E Crystallographic Communications 73, no. 7 (June 7, 2017): 983–86. http://dx.doi.org/10.1107/s2056989017008283.

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In the title compound, C10H14Cl3NO5, the five-membered dioxolane ring adopts an envelope conformation with the C atom bonded to the butenoate side chain as the flap. It deviates from the mean plane of the other atoms in the ring by 0.446 (6) Å. In the crystal, molecules are connected by O—H...O hydrogen bonds into helical chains running along theb-axis direction. The chains are linked into a sheet structure parallel to (001) by an N—H...O hydrogen bond. These classical hydrogen bonds enclose anR44(24) graph-set motif in the sheet structure. Furthermore, a weak intermolecular C—H...Cl interaction expands the sheet structures into a three-dimensional network.

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46

Lei, Xiaoyun, Shuai Huang, Hu Xiao, Feng Gao, and Xianli Zhou. "A New Taxane Diterpenoid and a New Neolignan from Taxus baccata." Natural Product Communications 13, no. 11 (November 2018): 1934578X1801301. http://dx.doi.org/10.1177/1934578x1801301103.

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Two new compounds, baccataxinine (1) and baccalignan (2), were isolated from the Taxus baccata, together with 16 known ones. Their structures were elucidated by comprehensive spectroscopic analyses of HR-ESI-MS, NMR and IR. Compound 1 is a taxane diterpenoid possessing a rare dioxolane ring between C-1 and C-2, while 2 is the first benzofuran neolignan from this species. Furthermore, they were also evaluated for their α-glucosidase inhibitory activity, but none of them showed considerable inhibitory effects.

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47

Morariu, Simona, Emil C. Buruiana, and Bogdan C. Simionescu. "Free-radical ring-opening polymerization of 2-(o-chlorophenyl)-4-methylene-1,3-dioxolane." Polymer Bulletin 30, no. 1 (January 1993): 7–12. http://dx.doi.org/10.1007/bf00296227.

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48

Ono, Daisuke, Shingo Yamamura, Masaki Nakamura, Tokuji Takeda, Araki Masuyama, and Yohji Nakatsuji. "Biodegradation of different carboxylate types of cleavable surfactants bearing a 1,3-dioxolane ring." Journal of the American Oil Chemists’ Society 72, no. 7 (July 1995): 853–56. http://dx.doi.org/10.1007/bf02541036.

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49

Memarian, Hamid Reza, and Sakineh Zare. "ChemInform Abstract: Diastereoselective 1,3-Dioxolane Formation by Photocatalytic Ring Opening of α-Epoxyketones." ChemInform 44, no. 45 (October 14, 2013): no. http://dx.doi.org/10.1002/chin.201345120.

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50

Popsavin, Velimir, Ljubica Radic, Mirjana Popsavin, and Vera Cirin-Novta. "Unexpected cycloreversion of a tosylated sugar oxetane under E2 conditions: The facile formation of 2-(2-furanyl)-1, 3-dioxolane from a novel 2, 5:4, 6-dianhydro-L-idose derivative (Preliminary commun." Journal of the Serbian Chemical Society 69, no. 2 (2004): 117–22. http://dx.doi.org/10.2298/jsc0402117p.

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2,5:4,6-Dianhydro-3-O-p-toluenesulfonyl-L-idose ethylene acetal (4) was synthesized with the aim of studying its chemical behaviour in the presence of several basic agents (Bu4NF/MeCN, NaOMe/MeOH, KOBut/ButOH/THF, and NaH/DMSO). Treatment of 4 with sodium hydride in dimethyl sulphoxide at room temperature unexpectedly gave the 2-(2-furanyl)-1,3-dioxolane. The mechanism of the process presumably involved the initial conversion of 4 to the corresponding 2,3-unsaturated derivative 5, followed by a facile oxetane ring cycloreversion by the elimination of formaldehyde.

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