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Journal articles on the topic 'Bicyclo[4.1.0]heptane'

Author: Grafiati

Published: 4 June 2021

Last updated: 1 February 2022

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1

Saunders, James, Chris Adamson, Yumeela Ganga-Sah, Andrew R. Lewis, and Andrew J. Bennet. "Rearrangement and nucleophilic trapping of bicyclo[4.1.0]hept-2-yl derived nonclassical bicyclobutenium ions." Canadian Journal of Chemistry 96, no. 2 (2018): 235–40. http://dx.doi.org/10.1139/cjc-2017-0569.

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Here we describe the synthesis of two specifically labelled 13C isotopologues of cis-2-(4-nitrophenoxy)bicyclo[4.1.0]heptane and their solvolysis reactions in trifluoroethanol. By using one- and two-dimensional 1H- and 13C-NMR spectroscopy, we characterized the pathways for the rearrangement of these isotopologues to give 13C-labelled 4-(2,2,2-trifluoroethoxy)cycloheptene. We show that the initially formed cationic intermediate undergoes a degenerate rearrangement, which does not reach equilibrium before nucleophilic capture of the cation. Moreover, we show that the nonclassical carbocation, c

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2

Parsons, E. J., and P. W. Jennings. "Platinacyclobutane chemistry: cis-disubstituted platinacyclobutane complex from bicyclo[4.1.0]heptane." Organometallics 7, no. 6 (1988): 1435–37. http://dx.doi.org/10.1021/om00096a032.

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3

Kazakova, �. Kh, L. N. Surkova, R. R. Shagidullin, S. V. Andreeva, G. Sh Bikbulatova, and A. N. Vereshchagin. "Conformation of trans-2-chlorohexanol and bicyclo[4.1.0]heptane halohydrins." Bulletin of the Academy of Sciences of the USSR Division of Chemical Science 35, no. 6 (1986): 1159–62. http://dx.doi.org/10.1007/bf00956587.

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4

Domı́nguez-Pérez, Beatriz, Éric Ferrer, Marta Figueredo, et al. "Synthesis of Novel Nucleoside Analogues Built on a Bicyclo[4.1.0]heptane Scaffold." Journal of Organic Chemistry 80, no. 19 (2015): 9495–505. http://dx.doi.org/10.1021/acs.joc.5b01413.

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5

SAKAI, Jun-ichi, Koji ISOGAI, Katsuya WATANABE, Kazue IKARASHI, Takashi HURUKAWA, and Hiroyuki KANAI. "Catalytic Hydrogenolysis of endo/exo-Amino- or Dimethylamino-substituted Bicyclo(3.1.0)hexane and Bicyclo(4.1.0)heptane." NIPPON KAGAKU KAISHI, no. 6 (1991): 741–47. http://dx.doi.org/10.1246/nikkashi.1991.741.

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6

Adachi, Hiroyuki, Akiyoshi Ueda, Toshio Aihara, Kazuyuki Tomida, Takashi Kawana, and Hideo Hosaka. "Synthesis of new bicyclo[4.1.0]heptane-2,4-dione derivatives and their herbicidal activity." Journal of Pesticide Science 32, no. 2 (2007): 112–19. http://dx.doi.org/10.1584/jpestics.g06-30.

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7

Su, Jing, Haiqun Tang, Brian A. McKittrick, et al. "Synthesis of novel bicyclo[4.1.0]heptane and bicyclo[3.1.0]hexane derivatives as melanin-concentrating hormone receptor R1 antagonists." Bioorganic & Medicinal Chemistry Letters 17, no. 17 (2007): 4845–50. http://dx.doi.org/10.1016/j.bmcl.2007.06.048.

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8

Collis, Gavin E., Dylan Jayatilaka, and Dieter Wege. "Cyclopropa-Fused Quinones. The Generation and Trapping of Bicyclo[4.1.0]hepta-1(6),3-diene-2,5-dione and 1H-Cyclopropa[b]naphthalene-2,7-dione." Australian Journal of Chemistry 50, no. 5 (1997): 505. http://dx.doi.org/10.1071/c96204.

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The title compounds (3) and (4) have been generated at low temperature by debromosilylation of 1-bromo-6-trimethylsilylbicyclo[4.1.0]hept-3-ene-2,5-dione (23) and 1a-bromo-7a-trimethylsilyl-1a,7a-dihydro-1H-cyclopropa[b]naphthalene-2,7-dione (38) respectively. Both cyclopropa-fused quinones are reactive but each could be trapped with furan to give a pair of cycloadducts, which were remarkably resistant to cycloreversion. In the absence of added trapping agent, the cyclopropanaphthoquinone (4) was intercepted by fluoride ion to give 1a-fluoro-1a,7a-dihydro-1H-cyclopropa[b]naphthalene-2,7-dione

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9

Crombie, Leslie, and Candida E. C. Fernando (née Lord). "The Heterogeneous Catalytic Hydrogenation of Cumulated Allene-cyclopropanes: 1-(2′-Methylpropenylidene)-7-bicyclo[4.1.0]heptane." Journal of Chemical Research, no. 7 (1998): 364–65. http://dx.doi.org/10.1039/a802162g.

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10

Dookhun, Veedeeta, and Andrew J. Bennet. "Synthesis and biological evaluation of a bicyclo[4.1.0]heptyl analogue of glucose-1-phosphate." Canadian Journal of Chemistry 82, no. 9 (2004): 1361–64. http://dx.doi.org/10.1139/v04-109.

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The synthesis of a bicyclo[4.1.0]heptyl analogue of glucose-1-phophate, (1R,2R,3S,4S,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)-bicyclo[4.1.0]heptan-2-yl dihydrogen phosphate (5) is reported. The synthetic route chosen started with methyl α-D-glucopyranoside and was accomplished in 11 steps with an overall yield of 3%. Compound 5 was tested as a potential substrate of UTP:α-D-glucose-1-phosphate uridylyltransferase, the enzyme that converts glucose-1-phosphate into UDP-glucose. However, the conformationally restricted glucose-1-phosphate analogue 5 was found to be a weakly binding inhibitor, ra

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11

Liu, Bang, Ren-Jie Song, Xuan-Hui Ouyang, Yang Li, Ming Hu, and Jin-Heng Li. "Palladium-catalyzed oxidative 6-exo-trig cyclization of 1,6-enynes: facile synthesis of bicyclo[4.1.0]heptan-5-ones." Chemical Communications 51, no. 64 (2015): 12819–22. http://dx.doi.org/10.1039/c5cc04300j.

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12

Werstiuk, N. H., S. Yeroushalmi, and Hong Guan-Lin. "Synthesis of bicyclic diones and thiones. Facile methylation of the enolates of bicyclo[2.2.1]heptane-2,5-dione and bicyclo[2.2.2]octane-2,5-dione. An AM1 computational study of bicyclic enolates." Canadian Journal of Chemistry 70, no. 3 (1992): 974–80. http://dx.doi.org/10.1139/v92-130.

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A group of bicyclic ketones and thiones have been synthesized for homenolization studies. Bicyclo[2.2.1]heptane-2,5-dione (6) undergoes unusually rapid tetramethylation giving 3,3,6,6-tetramethylbicyclo[2.2.1]heptane-2,5-dione (1) in good yield. Treatment of 1 with P2S5 in xylene gave 3,3,6,6-tetramethylbicyclo[2.2.1]heptane-2,5-dithione (2) and 3,3,6,6-tetramethyl 15-oxo-bicyclo[2.2.1]heptane-2-thione (3), which was converted into 4 with Raney nickel. Bicyclo[2,2,2]octane-2,5-dione (7), prepared via a Diels–Alder reaction between 2-trimethylsilyloxy-1,3-cyclohexadiene and and α-acetoxyacrylon

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13

Yang, Zhen, Ming-Jie Zhang, and Jie Zhu. "7-(p-Tolylsulfonyl)-7-azabicyclo[4.1.0]heptane." Acta Crystallographica Section E Structure Reports Online 62, no. 7 (2006): o3133—o3134. http://dx.doi.org/10.1107/s1600536806024512.

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The title compound, C13H17NO2S, is an aziridination product of cyclohexene using chloramine-T as a substrate. The aziridine ring is axially bound to the cyclohexane ring, which has a disordered half-chair-like conformation.

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14

Chinnakali, K., H. K. Fun, K. Sriraghavan, and V. T. Ramakrishnan. "7-(4-Nitrophenyl)-7-azabicyclo[4.1.0]heptane." Acta Crystallographica Section C Crystal Structure Communications 53, no. 12 (1997): IUC9700032. http://dx.doi.org/10.1107/s0108270197099241.

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15

Ihara, Masataka, Takahiko Taniguchi, Nobuaki Taniguchi, and Keiichiro Fukumoto. "A novel rearrangement of cyclobutanes to cyclopropanes; construction of tricyclo[5.4.0.0]undecane and bicyclo[4.1.0]heptane systems." Journal of the Chemical Society, Chemical Communications, no. 19 (1993): 1477. http://dx.doi.org/10.1039/c39930001477.

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16

Crossley, MJ, and AW Stamford. "Studies Directed Towards the Total Synthesis of Anticapsin and Related Compounds. III. A Ring-Fragmentation Route to the Anticapsin Skeleton." Australian Journal of Chemistry 47, no. 9 (1994): 1713. http://dx.doi.org/10.1071/ch9941713.

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The α-amino-5-oxo-7-oxabicyclo[4.1.0]heptane-2-propanoic acid framework of anticapsin and related compounds is generated by base-catalysed fragmentation of 2-amino-5,6-epoxy-1-hydroxybicyclo[2.2.2]octane-2-carboxylic acid derivatives in a retro-aldol-like reaction.

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17

Boualy, Brahim, Larbi El Firdoussi, Mustapha Ait Ali, Abdallah Karim, and Anke Spannenberg. "Crystal structure of (25,45,75)-7,7-dichloro-4-(1-chloro-1-methylethyl)- 1-(2,2,2-trichloroethyl)bicyclo[4.1.0]heptane, C12H16Cl6." Zeitschrift für Kristallographie - New Crystal Structures 224, no. 1-4 (2009): 665–66. http://dx.doi.org/10.1524/ncrs.2009.224.14.665.

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18

Jansen, Helen, J. Chris Slootweg, and Koop Lammertsma. "Valence isomerization of cyclohepta-1,3,5-triene and its heteroelement analogues." Beilstein Journal of Organic Chemistry 7 (December 21, 2011): 1713–21. http://dx.doi.org/10.3762/bjoc.7.201.

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The valence isomerization of the all-carbon and heteroelement analogues of cyclohepta-1,3,5-triene into the corresponding bicyclo[4.1.0]hepta-2,4-dienes is reviewed to show the impact of the heteroatom on the stability of both valence isomers. The focus is on the parent systems and their synthetic applications.

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19

Honda, Kiyoshi, Mari Konishi, Manabu Kawai, et al. "Stereoselective Synthesis of Bicyclo[3.1.1]Heptane Derivatives via Intramolecular Photocycloaddition Reaction." Natural Product Communications 7, no. 4 (2012): 1934578X1200700. http://dx.doi.org/10.1177/1934578x1200700410.

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Optically active 1,3-bridged cyclobutanes 10 of the bicyclo[3.1.1]heptane ring system and 1,2-bridged cyclobutanes 11 of the bicyclo[3.2.0]heptane ring system were produced by UV irradiation of α,β,γ,δ-unsaturated esters 9a and 9c-f. The preference of endo-stereochemistry at C-6 bridged head was observed in cross-adducts 10. On the other hand, irradiation of conjugated dienol9b led via only parallel cycloaddition to 1,2-bridged cyclobutane 11.

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20

IHARA, M., T. TANIGUCHI, N. TANIGUCHI, and K. FUKUMOTO. "ChemInform Abstract: A Novel Rearrangement of Cyclobutanes to Cyclopropanes; Construction of Tricyclo(5.4.0.01,3)undecane and Bicyclo(4.1.0)heptane Systems." ChemInform 25, no. 2 (2010): no. http://dx.doi.org/10.1002/chin.199402246.

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21

Tanase, Constantin I., Anamaria Hanganu, and Constantin Draghici. "Trifluoroacetylation of Alcohols During NMR Study of Compounds with Bicyclo[2.2.1]heptane, Oxabicyclo[3.3.0]octane and Bicyclo[3.3.0]octane Skeleton." Revista de Chimie 72, no. 2 (2021): 156–77. http://dx.doi.org/10.37358/rc.21.2.8428.

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TFA was added to a solution of a bicyclo[2.2.1]heptane azide-alcohol in CDCl3 to correctly characterize the compound, but during 24 h gave the trifluoro acetylated compound in quantitative yield. NMR spectra of the esterified compound helped us also to correctly attribute the NMR signals to the protons, and also confirmed the identification of the carbon atoms. The study was extended to other 14 compounds containing a primary alcohol group alone or with an ethylene ketal, a δ- or -lactone group, a primary and a secondary group, two primary and an alkene group and two primary and a secondary a

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22

Katayama, Sadamu, and Masashige Yamauchi. "Photochemical Synthesis of Bicyclo[4.1.0]hept-2-enes." Chemistry Letters 24, no. 4 (1995): 311–12. http://dx.doi.org/10.1246/cl.1995.311.

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23

Tsurusaki, Akihiro, Jun Kamiyama, and Soichiro Kyushin. "Tetrasilane-Bridged Bicyclo[4.1.0]heptasil-1(6)-ene." Journal of the American Chemical Society 136, no. 37 (2014): 12896–98. http://dx.doi.org/10.1021/ja507279z.

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24

Shen, Quang, Vladimir S. Mastryukov, and James E. Boggs. "The structure of bicyclo[3.1.0]hexane as determined by electron diffraction and microwave spectroscopy. Reinvestigation with ab initio calculations. Calculated structure of bicyclo[4.1.0]heptane." Journal of Molecular Structure 352-353 (June 1995): 181–91. http://dx.doi.org/10.1016/0022-2860(95)08827-i.

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25

Ji, Jianguo, William H. Bunnelle, Tao Li та ін. "Discovery of fused azetidines as novel selective α4β2 neuronal nicotinic receptor (NNR) agonists". Pure and Applied Chemistry 77, № 12 (2005): 2041–45. http://dx.doi.org/10.1351/pac200577122041.

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An efficient synthesis of (1R,5S)-6-(5-cyano-3-pyridinyl)-3,6-diaza-bicyclo[3.2.0]heptane A-366833, a novel potent selective neuronal nicotinic receptor (NNR) agonist, is described. The enantiomerically pure pharmacophore benzyl (1S,5S)-3,6-diaza-bicyclo[3.2.0]heptane-3-carbamate was successfully constructed from benzyl N-allyl-N-(2-hydroxyimino-ethyl)-carbamate through a convenient approach including an intramolecular [1,3]-dipolar cycloaddition, reductive ring-opening reaction, chiral resolution, and intramolecular cyclization. Subsequent N-arylation of the pharmacophore with 3-bromo-5-cyano

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26

Napolitano, Carmela, Manuela Borriello, Francesca Cardullo, Daniele Donati, Alfredo Paio, and Stefano Manfredini. "Synthesis of 3-azabicyclo[4.1.0]heptane-1-carboxylic acid." Tetrahedron 66, no. 29 (2010): 5492–97. http://dx.doi.org/10.1016/j.tet.2010.05.006.

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27

Hřebabecký, Hubert, Milena Masojídková, Martin Dračínský, and Antonín Holý. "Synthesis of Novel Conformationally Locked Carbocyclic Nucleosides Derived from 3-(Hydroxymethyl)bicyclo[2.2.1]heptane-2,5-diol." Collection of Czechoslovak Chemical Communications 71, no. 6 (2006): 871–88. http://dx.doi.org/10.1135/cccc20060871.

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(1R*,2R*,3R*,4R*,5R*,6S*)-3-Amino-5-(benzyloxy)-6-(hydroxymethyl)bicyclo[2.2.1]heptan-2-ol (18) was prepared in seven easy steps from benzyl (1R*,2S*,3S*,4S*)-3-(benzyloxy)bicyclo[2.2.1]hept-5-ene-2-carboxylate (10). Reaction of amine18with ethylN-((2E)-3-ethoxymethacryloyl)carbamate afforded 1-[(1R*,2R*,3R*,4R*,5S*,6R*)-6-(benzyloxy)-3-hydroxy-5- (hydroxymethyl)bicyclo[2.2.1]heptan-2-yl]-5-methylpyrimidine-2,4(1H,3H)-dione (21) and after deprotection by transfer hydrogenation, free thymine analogue22. The thymine derivative21was converted to 2,3'-anhydronucleoside26. Treatment of the benzyl d

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28

Boualy, Brahim, Larbi El Firdoussi, Mustapha Ait Ali, Abdallah Karim, and Anke Spannenberg. "Crystal structure of (2S,4S,7S)-7,7-dichloro-4-(1-chloro-1-methylethyl)- 1-(2,2,2-trichloroethyl)bicyclo[4.1.0]heptane, C12H16Cl6." Zeitschrift für Kristallographie - New Crystal Structures 224, no. 4 (2009): 631–32. http://dx.doi.org/10.1524/ncrs.2009.0278.

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29

Tănase, Constantin I., Constantin Drăghici, Anamaria Hanganu, et al. "1′-Homocarbocyclic Nucleoside Analogs with an Optically Active Substituted Bicyclo[2.2.1]Heptane Scaffold." Chemistry Proceedings 3, no. 1 (2020): 16. http://dx.doi.org/10.3390/ecsoc-24-08367.

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An optically active bicyclo[2.2.0]heptane fragment was introduced in the molecule of new 1′-homonucleosides on a 2- 6-chloro-amino-purine scaffold to obtain 6-substituted carbocyclicnucleozide analogs as antiviral compounds. The synthesis was realized by a Mitsunobu reaction of the base with the corresponding bicyclo[2.2.0]heptane intermediate, and then the nucleoside analogs were obtained by substitution of the 6-chlorime with selected pharmaceutically accepted amines. A molecular docking study of the compounds on influenza, HSV and low active coronavirus was realized. Experimental screening

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30

Che, Jin-Xin, Zhi-Long Wang, Xiao-Wu Dong, You-Hong Hu, Xin Xie, and Yong-Zhou Hu. "Bicyclo[2.2.1]heptane containing N,N′-diarylsquaramide CXCR2 selective antagonists as anti-cancer metastasis agents." RSC Advances 8, no. 20 (2018): 11061–69. http://dx.doi.org/10.1039/c8ra01806e.

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31

Sadyrbekov, Daniyar, Timur Saliev, Yuri Gatilov, et al. "Spatial Structure and Antimicrobial Activity of Cyclopropane Derivative of Limonene." Natural Product Communications 13, no. 4 (2018): 1934578X1801300. http://dx.doi.org/10.1177/1934578x1801300401.

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A cyclopropane derivative of limonene, (1 S, 4 S, 6 R)-7,7-dichloro-4-[(1 S)-2,2-dichloro-1-methylcyclopropyl]-1-methylbicyclo [4.1.0] heptane (compound 2), was synthesized and its structure was determined by NMR and X-ray crystallographic methods. In addition, an antimicrobial activity of the compound against Gram-positive ( Staphylococcus aureus, Bacillus subtilis) and Gram-negative ( Escherichia coli, Pseudomonas aeruginosa) bacterial strains was also scrutinized.

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32

Hřebabecký, Hubert, Milena Masojídková, and Antonín Holý. "Synthesis of Racemic 2-Hydroxy-4- and 2-Hydroxy-5-(hydroxymethyl)cyclohexane Nucleoside Analogues." Collection of Czechoslovak Chemical Communications 67, no. 11 (2002): 1681–99. http://dx.doi.org/10.1135/cccc20021681.

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New racemic 2-hydroxy-4- and 2-hydroxy-5-(hydroxymethyl)cyclohexane analogues of adenine (10b and 16b) and thymine nucleosides (13b and 19b) were prepared by alkylation of 1,8-diazabicyclo[5.4.0]undec-7-ene salt of adenine and/or thymine with 3-vinyl-7-oxabicyclo[4.1.0]heptane followed by cis hydroxylation with osmium(VIII) oxide and sodium chlorate, oxidation with sodium periodate, and borohydride reduction.

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33

Rehse, Klaus, Peter Sparfeldt, and Wolfgang Kehr. "Neuropsychotrope aktivität dopaminanaloger bicyclo[2.2.1]-heptane." Archiv der Pharmazie 320, no. 10 (1987): 1042–50. http://dx.doi.org/10.1002/ardp.198700007.

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34

Walton, John C. "Homolytic rearrangements of bicyclo[2.2.0]hexane and bicyclo[3.2.0]heptane." Journal of the Chemical Society, Perkin Transactions 2, no. 7 (1988): 1371. http://dx.doi.org/10.1039/p29880001371.

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35

Barnier, J. P., V. Rayssac, V. Morisson, and L. Blanco. "Enzymatic resolution of endo-bicyclo[4.1.0]heptan-2-ols." Tetrahedron Letters 38, no. 49 (1997): 8503–6. http://dx.doi.org/10.1016/s0040-4039(97)10299-4.

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36

Alkorta, Ibon, Fernando Blanco, and José Elguero. "Does 7-norcaranone (bicyclo[4.1.0]heptan-7-one) exist?" Journal of Molecular Structure: THEOCHEM 896, no. 1-3 (2009): 92–95. http://dx.doi.org/10.1016/j.theochem.2008.11.005.

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37

Chittimalla, Santhosh Kumar, and Chennakesavulu Bandi. "Rapid entry to functionally rich bicyclo[4.1.0]heptenone systems." RSC Advances 3, no. 33 (2013): 13663. http://dx.doi.org/10.1039/c3ra42282h.

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38

Billups, W. E., Weimei Luo, Gon-Ann Lee, et al. "Synthesis and Chemistry of Bicyclo[4.1.0]hept-1,6-ene†." Journal of Organic Chemistry 61, no. 2 (1996): 764–70. http://dx.doi.org/10.1021/jo951559y.

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39

Chung, Young Keun, Kyung-Mi Chang, and Ju Hyun Kim. "A Versatile Synthetic Platform Based on Bicyclo[4.1.0]heptenes." Journal of Inorganic and Organometallic Polymers and Materials 24, no. 1 (2013): 15–32. http://dx.doi.org/10.1007/s10904-013-9935-5.

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40

Liu, Qi Mei, та Wan Xi Peng. "80°С-Based TD-GC/MS Analysis of Chemical Components from Branches of Cinnamomum camphora". Key Engineering Materials 480-481 (червень 2011): 466–71. http://dx.doi.org/10.4028/www.scientific.net/kem.480-481.466.

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The analytical result by 80°С-based TD-GC/MS showed that 65 peaks were obtained from the helium volatiles from the fresh branches of Cinnamomum camphora and 60 chemical compounds were identified. The results showed that the main components were as: 1,3-Benzodioxole, 5-(2-propenyl)- (12.629%), Tricyclo[2.2.1.0(2,6)]heptane, 1,7-dimethyl-7-(4-methyl-3-pentenyl)-, (-)- (10.302%), 3-Cyclohexene-1-methanol, .alpha.,.alpha.4-trimethyl- (9.084%), Bicyclo[2.2.1] heptan-2-one, 1,7,7-trimethyl-, (1R)- (7.406%), Nerolidol (6.695%), Bicyclo[2.2.1]heptane, 2-methyl-3-methylene-2-(4-methyl-3-pentenyl)-, (1S

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41

Christl, Manfred, Max Braun, and Oliver Deeg. "Photochemical reactions of tetrachloro-1,4-benzoquinone (chloranil) with tricyclo[4.1.0.02,7]heptane (Moore's hydrocarbon) and bicyclo[4.1.0]hept-2-ene (2-norcarene)." Organic & Biomolecular Chemistry 11, no. 17 (2013): 2811. http://dx.doi.org/10.1039/c3ob27305a.

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42

Jana, Anupam, Sujit Mondal, and Subrata Ghosh. "Studies towards the synthesis of bielschowskysin. Construction of the highly functionalized bicyclo[3.2.0]heptane segment." Organic & Biomolecular Chemistry 13, no. 6 (2015): 1846–59. http://dx.doi.org/10.1039/c4ob02182g.

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43

Wermuth, Urs D., Ian D. Jenkins, Raymond C. Bott, Karl A. Byriel, and Graham Smith. "Some Stereochemical Aspects of the Strecker Synthesis and the Bucherer - Bergs Reaction." Australian Journal of Chemistry 57, no. 5 (2004): 461. http://dx.doi.org/10.1071/ch03202.

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Both the Strecker and Bucherer–Bergs reactions convert the norbornane keto ester methyl bicyclo[2.2.1]hept-6-one-2-endo-carboxylate into the lactam 6-endo-aminobicyclo[2.2.1]heptane-2-endo-carboxylic acid-γ-lactam-6-exo-carboxylic acid. This lactam is unusually stable and cannot be hydrolyzed to the corresponding amino acid. The stereochemistry in the Strecker reaction, in which the amino group is endo, is contrary to that expected from literature precedent. The stereochemistry in the Bucherer–Bergs reaction, in which the amino group is also endo, has been confirmed by X-ray crystallographic a

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44

Tanase, Constantin I., Constantin Draghici, Catalina Negut, and Lucia Pintilie. "New Constrained Amines in a Bicyclo[2.2.1]Heptane Skeleton." Revista de Chimie 69, no. 9 (2018): 2448–53. http://dx.doi.org/10.37358/rc.18.9.6551.

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In this paper we present an efficient procedure for obtaining ether-protected bicyclo[2.2.1]heptane amines in six steps, from an optically active keto-alcohol norbornane compound, for building the heterocyclic bases of pyrimidine and purine constrained nucleosides. Trityl as protecting group makes it possible to isolate 5-endo-compounds in pure form by selective crystallization, and to isolate the intermediates in the next 3 steps of the reaction by crystallization. With TBDMS, all compounds were obtained as oil. The direct selective reduction of the keto-alcohol norbornane compound gave the p

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Liu, Qi Mei, Dang Quan Zhang, Kuan Peng та Wan Xi Peng. "Deep Analysis on Bioindustry Prospects of 40°С Volatiles of Cinnamomum camphora Branches". Key Engineering Materials 480-481 (червень 2011): 266–71. http://dx.doi.org/10.4028/www.scientific.net/kem.480-481.266.

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Cinnamomum camphora has been used to heal some specific diseases in the Chinese Folk for a long time. In order to explore the wide utilization in biomedicine and spicery, the chemical components of helium volatiles from the fresh branches of C. camphora were studied by TD-GC/MS. The analytical result by TD-GC/MS showed that 50 peaks were obtained from the helium volatiles from the fresh branches of C. camphora and 46 chemical compounds representing 99.993% of the total areas were identified. The results showed that the main components were as: Bicyclo[2.2.1]heptan-2-one, 1,7,7-trimethyl-, (1R)

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46

Sims, CG, BW Skelton, D. Wege, and AH White. "Some Transformations of 1,6,7,7-Tetrachlorobicyclo[4.1.0]heptan-3-one. Crystal and Molecular Structure of 4-(Dichloromethylene)-1-methyl-5,6-dihydro-1h-indazol-7(4H)-one." Australian Journal of Chemistry 44, no. 11 (1991): 1575. http://dx.doi.org/10.1071/ch9911575.

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Treatment of the title tetrachloro ketone with triethylamine generates 6,7,7-trichlorobicyclo-[4.1.0]hept-1(2)-en-3-one (4), which can be trapped by furan to give two cycloadducts. In the absence of trapping agent, compound (4) undergoes a methylenecyclopropane rearrangement to yield 5-chloro-6-( dichloromethylene ) bicyclo [3.1.0]hexan-2-one. The strained enone (4) can also be intercepted by diazomethane, which affords the title indazolone, whose characterization was supported by a single-crystal X-ray study.

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47

Fu, Jian-Guo, Yi-Fan Shan, Wang-Bin Sun, Guo-Qiang Lin, and Bing-Feng Sun. "An asymmetric approach to bicyclo[2.2.1]heptane-1-carboxylates via a formal [4 + 2] cycloaddition reaction enabled by organocatalysis." Organic & Biomolecular Chemistry 14, no. 23 (2016): 5229–32. http://dx.doi.org/10.1039/c6ob00814c.

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An organocatalytic formal [4 + 2] cycloaddition reaction has been developed that permits rapid access to bicyclo[2.2.1]heptane-1-carboxylates with excellent enantioselectivities under mild and operationally simple conditions.

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48

Walton, John C. "Free radical reactions of bicyclo[2.1.1]hexane and bicyclo[2.2.1]heptane." Journal of the Chemical Society, Perkin Transactions 2, no. 11 (1988): 1989. http://dx.doi.org/10.1039/p29880001989.

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Baser, K. Hüsnü Can, Nurhayat Tabanca, Nese Kirimer, Erdal Bedir, Ikhlas A. Khan, and David E. Wedge. "Recent advances in the chemistry and biological activities of the Pimpinella species of Turkey." Pure and Applied Chemistry 79, no. 4 (2007): 539–56. http://dx.doi.org/10.1351/pac200779040539.

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Two new natural products incorporating a phenylpropyl subunit ("phenylpropanoids"), [4-(prop-2-enyl)phenyl angelate and 4-(3-methyloxiranyl)phenyl 2-methylbutyrate], one new bisabolene-type sesquiterpenoid [1-methyl-4-(6-methylhepta-1,5-dien-2-yl)-7-oxabicyclo[4.1.0]heptane ("aureane")], and one new trinorsesquiterpene [4-(6-methylbicyclo[4.1.0]hept-2-en-7yl)butan-2-one ("traginone")] have been isolated from the essential oils of Pimpinella species occurring in Turkey, together with nine known phenylpropanoids and other natural products. Six of the known compounds are newly reported for Umbell

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Moilanen, Maija, Kalle Manninen, Kurt B. G. Torssell, Jyrki M. Loponen, Erkki K. Euranto, and Tore Pettersson. "Aminomethylation of Bicyclo[2.2.1]heptane-2,5-dione." Acta Chemica Scandinavica 44 (1990): 857–59. http://dx.doi.org/10.3891/acta.chem.scand.44-0857.

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