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Journal articles on the topic 'Bicyclo[3.1.0]hexan'

Author: Grafiati

Published: 4 June 2021

Last updated: 14 February 2022

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1

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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2

Mennen, Steven, Athimoolam Arunachalampillai, Deborah Choquette, Harikrishna Muppalla, and Krishna Sheena. "Scalable Synthesis of 6,6-Dimethylbicyclo[3.1.0]hexan-3-one." Synlett 28, no. 17 (2017): 2330–34. http://dx.doi.org/10.1055/s-0036-1588484.

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A simple five-step process for the conversion of technical grade (+)-3-carene into 6,6-dimethylbicyclo[3.1.0]hexan-3-one was developed. A robust process was required that delivered the 6,6-dimethylbicyclo[3.1.0]hexan-3-one, minimized chromatography, reduced the excess of silver salts, and avoided toxic chromium oxidants. A simple and scalable process that relies on crystallization and distillation was developed and demonstrated to produce hundreds of grams of 6,6-dimethylbicyclo[3.1.0]hexan-3-one.

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3

Sorensen, T. S., and F. Sun. "In situ preparation of cyclopropanones with the bicyclo[3.1.0]hexan-6-one skeleton (substituted examples of the Loftfield intermediate). Confirmation of a very facile intramolecular alkyl cyclopropanone – dienol rearrangement." Canadian Journal of Chemistry 74, no. 1 (1996): 79–87. http://dx.doi.org/10.1139/v96-010.

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Four substituted bicyclo[3.1.0]hexan-6-ones (cyclopropanones) were prepared in situ, starting from the corresponding 2,6-dibromocyclohexanone and reductively removing the bromine atoms with the organometallic salt PPN+Cr(CO)4NO− The reaction is essentially instantaneous at −78 or−100 °C, and can be conveniently carried out in an NMR tube for easy characterization of the products by low-temperature 1H and 13C NMR spectroscopy. The1,5-di-tert-butyl and 1-tert-butyl analogs were thermally stable to ca. 0 °C, but the 1-tert-butyl-5-methyl and 1-tert-butyl-5-ethyl derivatives were extremely labile,

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4

Kirmse, Wolfgang, and Georg Hellwig. "Desaminierungsreaktionen, 51. Zerfall von Bicyclo[3.1.0]hexan-exo-6-diazonium-Ionen." Chemische Berichte 122, no. 2 (1989): 389–92. http://dx.doi.org/10.1002/cber.19891220231.

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5

Nishino, Hiroshi, and Kentaro Asahi. "Synthesis of Bicyclo[3.1.0]hexan-2-ones by Manganese(III) Oxidation in Ethanol." Synthesis 2009, no. 03 (2009): 409–23. http://dx.doi.org/10.1055/s-0028-1083324.

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6

Wang, Xiaoxia, Jianyong Li, Ting Yuan, Bingxin You, Guanqun Xie, and Xin Lv. "Additive Tuned Selective Synthesis of Bicyclo[3.3.0]octan-1-ols and Bicyclo[3.1.0]hexan-1-ols Mediated by AllylSmBr." Journal of Organic Chemistry 83, no. 16 (2018): 8984–94. http://dx.doi.org/10.1021/acs.joc.8b01170.

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7

Choo, Jaebum, Whe-Yi Chiang, Soo-No Lee, and Jaan Laane. "Far-Infrared Spectra and Ring-Puckering Potential Energy Function of Bicyclo[3.1.0]hexan-3-one." Journal of Physical Chemistry 99, no. 30 (1995): 11636–39. http://dx.doi.org/10.1021/j100030a002.

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8

Hamon, DPG, and NJ Shirley. "A Convenient Synthesis of 5-Alkylbicyclo[3.1.0]hexan-2-ones Including the Natural Product Sabina Ketone." Australian Journal of Chemistry 40, no. 7 (1987): 1321. http://dx.doi.org/10.1071/ch9871321.

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Simple 5-alkylbicyclo[3.1.0]hexan-2-ones, including the natural product sabina ketone, can be prepared in four steps from aromatic ethers via Birch reduction, hydrogen chloride addition, hydrolysis and then base treatment of the resultant 4-chlorocyclohexanones.

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9

Maslivetc, Vladimir, Colby Barrett, Nicolai A. Aksenov, Marina Rubina, and Michael Rubin. "Intramolecular nucleophilic addition of carbanions generated from N-benzylamides to cyclopropenes." Organic & Biomolecular Chemistry 16, no. 2 (2018): 285–94. http://dx.doi.org/10.1039/c7ob02068f.

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An unusual reaction is described, involving a formal intramolecular nucleophilic substitution of bromocyclopropanes with nitrogen ylides generated in situ from N-benzyl carboxamides. This reaction involves cyclopropene intermediates and allows for the facile preparation of 3-azabicyclo[3.1.0]hexan-2-ones.

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10

Watanabe, Mizuki, Takaaki Kobayashi, Yoshihiko Ito, Shizuo Yamada, and Satoshi Shuto. "Conformational Restriction of Histamine with a Rigid Bicyclo[3.1.0]hexane Scaffold Provided Selective H3 Receptor Ligands." Molecules 25, no. 16 (2020): 3562. http://dx.doi.org/10.3390/molecules25163562.

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We designed and synthesized conformationally rigid histamine analogues with a bicyclo[3.1.0]hexane scaffold. All the compounds were selectively bound to the H3 receptor subtype over the H4 receptor subtype. Notably, compound 7 showed potent binding affinity and over 100-fold selectivity for the H3 receptors (Ki = 5.6 nM for H3 and 602 nM for H4). These results suggest that the conformationally rigid bicyclo[3.1.0]hexane structure can be a useful scaffold for developing potent ligands selective for the target biomolecules.

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11

Liu, Qi Mei, and Wan Xi Peng. "Py-GC/MS Analysis of Bioactive Components of 450°C Pyrolyzate from Ethanol Extractives of Oil-Tea Cake." Key Engineering Materials 480-481 (June 2011): 513–18. http://dx.doi.org/10.4028/www.scientific.net/kem.480-481.513.

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450°C-based pyrolysis- GC/MS technology was used to analyze the bioactive components of ethanol extractives of oil-tea cake. The analytical result showed that 38 peaks were obtained from the 450°C-based pyrolyzate of ethanol extractives of oil-tea cake, and 37 compounds representing 97.81 % of the total areas were identified (Table 1). The analytical result showed that the main components of ethanol extractives of oil-tea cake by 450°C-based pyrolysis- GC/MS were as: Benzene, 1,2,3-Trimethoxy-5-Methyl- (21.56%), Phenol, 3,4-Dimethoxy- (16.31%), 3',5'-Dimethoxyacetophenone (14.37%), 1,2-Ethaned

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12

Mohammed, Lana MA, Tara Faeq M. Salah, and Karzan O. Qader. "Chemical composition and antifungal activity of Mentha spicata L. plant from Sulaimaniyah in Iraq." Kurdistan Journal of Applied Research 2, no. 1 (2017): 52–56. http://dx.doi.org/10.24017/science.2017.1.11.

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Aerial parts of Mentha plants were collected from Sulaimaniyah city, during 15th Mar to 1st July2016. Clevenger apparatus was used for plant sample distillation and then obtained essential oils were analyzed by GC and GC/MS. The GC–MS analysis resulted in the detection of thirty-eight compounds which made up 100% of the total plant essential oil. The major components of the oil were (54.44%) of 2-Cyclohexen-1-one, 2-methyl-5-(1- methylethenyl)-, (R)-, (27.72%) of D-Limonene, (3.29%) of 2-Cyclohexen-1-ol, 2-methyl-5-(1- methylethenyl)-, trans-, (2.16%) of Cyclohexanol, 2- methyl-5-(1-methylethe

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13

Childs, Ronald F., and Baha E. George. "A quantitative examination of the photoisomerization of some protonated phenols." Canadian Journal of Chemistry 66, no. 6 (1988): 1343–49. http://dx.doi.org/10.1139/v88-217.

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The photoisomerization of a series of protonated, methyl substituted phenols to protonated bicyclo[3.1.0]hexenones has been examined. These reactions, which were carried out in CF3SO3H as a strong acid solvent at ambient temperatures, provide a convenient route to a variety of bicyclo[3.1.0]hexenones. The quantum yields for these photoisomerizations vary from 0.018 for protonated 3,5-dimethylphenol to 0.65 for protonated 2,6-dimethylphenol. This variation in efficiency can be understood in terms of a competition between ring opening, to regenerate the starting phenol, or cyclopropyl migration,

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14

Kuehl, Philip J., Michael D. Carducci, and Paul B. Myrdal. "4-Imino-1,3-diazabicyclo[3.1.0]hexan-2-one." Acta Crystallographica Section E Structure Reports Online 62, no. 9 (2006): o3688—o3690. http://dx.doi.org/10.1107/s1600536806029412.

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15

Wang, Yue, Manman Song, Er-Qing Li, and Zheng Duan. "Auto-tandem palladium/phosphine cooperative catalysis: synthesis of bicyclo[3.1.0]hexenes by selective activation of Morita–Baylis–Hillman carbonates." Organic Chemistry Frontiers 8, no. 13 (2021): 3366–71. http://dx.doi.org/10.1039/d1qo00330e.

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16

Feierfeil, Johannes, Adriana Grossmann, and Thomas Magauer. "Ring Opening of Bicyclo[3.1.0]hexan-2-ones: A Versatile Synthetic Platform for the Construction of Substituted Benzoates." Angewandte Chemie 127, no. 40 (2015): 12001–4. http://dx.doi.org/10.1002/ange.201506232.

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17

Feierfeil, Johannes, Adriana Grossmann, and Thomas Magauer. "Ring Opening of Bicyclo[3.1.0]hexan-2-ones: A Versatile Synthetic Platform for the Construction of Substituted Benzoates." Angewandte Chemie International Edition 54, no. 40 (2015): 11835–38. http://dx.doi.org/10.1002/anie.201506232.

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18

Wang, Kai-Bing, Rui-Qiao Ran, Shi-Dong Xiu, and Chuan-Ying Li. "Synthesis of 3-Aza-bicyclo[3.1.0]hexan-2-one Derivatives via Gold-Catalyzed Oxidative Cyclopropanation of N-Allylynamides." Organic Letters 15, no. 10 (2013): 2374–77. http://dx.doi.org/10.1021/ol4007629.

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19

Muriel, Bastian, Alec Gagnebin, and Jerome Waser. "Synthesis of bicyclo[3.1.0]hexanes by (3 + 2) annulation of cyclopropenes with aminocyclopropanes." Chemical Science 10, no. 46 (2019): 10716–22. http://dx.doi.org/10.1039/c9sc03790j.

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20

Pelties, Stefan, Andreas W. Ehlers, and Robert Wolf. "Insertion of phenyl isothiocyanate into a P–P bond of a nickel-substituted bicyclo[1.1.0]tetraphosphabutane." Chemical Communications 52, no. 39 (2016): 6601–4. http://dx.doi.org/10.1039/c6cc01572g.

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A nickel-substituted bicyclo[1.1.0]tetraphosphabutane is obtained by reacting an NHC-based cyclopentadienyl nickel(i) radical with P<sub>4</sub>. The CS and CN bonds of phenyl isothiocyanate insert into a P–P bond of the “P<sub>4</sub> butterfly” skeleton, affording new complexes with a unique bicyclo[3.1.0]heterohexane framework.

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21

Piers, Edward, and Grace L. Jung. "Thermal rearrangement of functionalized 6-exo-(1-alkenyl)bicyclo[3.1.0]hex-2-enes. A total synthesis of (±)-sinularene." Canadian Journal of Chemistry 63, no. 4 (1985): 996–98. http://dx.doi.org/10.1139/v85-167.

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A total synthesis of the racemic form of the marine sesquiterpenoid (−)-sinularene (1) is described. The key step of the synthesis involved the stereoselective thermal rearrangement of the highly functionalized bicyclo[3.1.0]hexene 12 to provide, in 86% yield, the substituted bicyclo[3.2.1]octadiene 13. Conversion of the latter substance into (±)-sinularene (1) was accomplished via an efficient 4-step sequence.

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22

Yufit, Dmitrii S., Viktor Bagutskii, Judith A. K. Howard, and Armin de Meijere. "Methylexo-bicyclo[3.1.0]hexane-6,6-dicarboxylate." Acta Crystallographica Section E Structure Reports Online 59, no. 11 (2003): o1610—o1612. http://dx.doi.org/10.1107/s1600536803021433.

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23

Kirmse, Wolfgang, and Aribert Wonner. "Reaktionen Pentafluorethyl-substituierter Bicyclo[2.1.1]hexan-Derivate." Chemische Berichte 126, no. 2 (1993): 409–14. http://dx.doi.org/10.1002/cber.19931260218.

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24

Toti, Kiran S., Shanu Jain, Antonella Ciancetta, et al. "Pyrimidine nucleotides containing a (S)-methanocarba ring as P2Y6 receptor agonists." MedChemComm 8, no. 10 (2017): 1897–908. http://dx.doi.org/10.1039/c7md00397h.

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Uracil nucleotides containing a south-bicyclo[3.1.0]hexane ((S)-methanocarba) ring system in place of the ribose ring were synthesized and shown to be potent P2Y<sub>6</sub>R agonists in a calcium mobilization assay.

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25

Wang, Kai-Bing, Rui-Qiao Ran, Shi-Dong Xiu, and Chuan-Ying Li. "ChemInform Abstract: Synthesis of 3-Aza-bicyclo[3.1.0]hexan-2-one Derivatives via Gold-Catalyzed Oxidative Cyclopropanation of N-Allylynamides." ChemInform 44, no. 37 (2013): no. http://dx.doi.org/10.1002/chin.201337107.

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26

Feierfeil, Johannes, Adriana Grossmann, and Thomas Magauer. "ChemInform Abstract: Ring Opening of Bicyclo[3.1.0]hexan-2-ones: A Versatile Synthetic Platform for the Construction of Substituted Benzoates." ChemInform 47, no. 5 (2016): no. http://dx.doi.org/10.1002/chin.201605104.

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27

Oh, Chang Ho, Su Jin Lee, Ji Ho Lee, and Yoon Jung Na. "Regioselectivities in alkyne activation: synthesis of 2-(bicyclo[3.1.0]hexan-1-yl)furan derivatives by Au-catalyzed cyclization and cyclopropanation." Chemical Communications, no. 44 (2008): 5794. http://dx.doi.org/10.1039/b812077c.

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28

Zhang, Lei, Bruce N. Rogers, Allen J. Duplantier, et al. "3-(Imidazolyl methyl)-3-aza-bicyclo[3.1.0]hexan-6-yl)methyl ethers: A novel series of mGluR2 positive allosteric modulators." Bioorganic & Medicinal Chemistry Letters 18, no. 20 (2008): 5493–96. http://dx.doi.org/10.1016/j.bmcl.2008.09.026.

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29

Xue, Jie-You, Shi-Xiong Tang, Ai-Bin Sun, et al. "Synthesis of 4-substituted 3-oxabicyclo[3.1.0]hexan-2-one." Chinese Journal of Chemistry 10, no. 5 (2010): 445–50. http://dx.doi.org/10.1002/cjoc.19920100511.

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30

Kremer, Adrian, Bernadette Norberg, Alain Krief, and Johan Wouters. "endo-3,3-Dimethyl-4-oxobicyclo[3.1.0]hexan-2-yl methanesulfonate." Acta Crystallographica Section E Structure Reports Online 66, no. 4 (2010): o948. http://dx.doi.org/10.1107/s1600536810010901.

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31

Ricci, Andrea, Elisa Fasani, Mariella Mella, and Angelo Albini. "Photochemistry of some steroidal bicyclo[3.1.0]hexenones." Tetrahedron 60, no. 1 (2004): 115–20. http://dx.doi.org/10.1016/j.tet.2003.10.090.

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32

Dauben, William G., Jeffrey M. Cogen, Victor Behar, Arthur G. Schultz, William Geiss, and Arthur G. Taveras. "Wavelength dependent photoisomerization of bicyclo[3.1.0]hexenones." Tetrahedron Letters 33, no. 13 (1992): 1713–16. http://dx.doi.org/10.1016/s0040-4039(00)91713-1.

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33

Childs, Ronald F., and Baha E. George. "Thermal isomerizations of protonated bicyclo[3.1.0]hexenones." Canadian Journal of Chemistry 66, no. 6 (1988): 1350–54. http://dx.doi.org/10.1139/v88-218.

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The thermal isomerization of a wide range of protonated methyl substituted bicyclo[3.1.0]hex-3-en-2-ones to protonated phenols has been examined using triflic acid as a strong acid solvent. The rate constants and activation energies of these isomerizations have been determined. The barriers to the isomerizations were shown to be dependent on the number and position of the methyl substituents. The results show that three different mechanisms are needed to account for these isomerizations, two of which involve a preliminary circumambulatory rearrangement prior to ring opening and the other proce

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34

Api, A. M., F. Belmonte, D. Belsito, et al. "RIFM fragrance ingredient safety assessment, bicyclo[3.1.0]hexan-3-one, 4-methyl-1-(1-methylethyl)-, CAS Registry Number 1125-12-8." Food and Chemical Toxicology 134 (December 2019): 110724. http://dx.doi.org/10.1016/j.fct.2019.110724.

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35

Quast, Helmut, Josef Walter Stawitz, and Bodo Mueller. "Synthesis, Reactions, and Rearrangements of 2,4-Diazabicyclo[3.1.0]hexan-3-ones." HETEROCYCLES 85, no. 10 (2012): 2449. http://dx.doi.org/10.3987/com-12-12543.

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36

Görbitz, Carl Henrik, Tore Hansen, and Kristian Vestli. "(1S,5R)-1-(3,4-Dichlorophenyl)-3-oxabicyclo[3.1.0]hexan-2-one." Acta Crystallographica Section E Structure Reports Online 65, no. 4 (2009): o686. http://dx.doi.org/10.1107/s1600536809007533.

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37

Hrovat, David A., Arvi Rauk, T. S. Sorensen, Helen K. Powell, and Weston Thatcher Borden. "Ring Opening of Bicyclo[n.1.0]alkanones to 2-Cycloalkanone-1,3-diyls. Why Does Oxyallyl Diradical Formation Require Less Energy from Bicyclo[3.1.0]hexan-6-ones than from Bicyclo[1.1.0]butan-2-ones?" Journal of the American Chemical Society 118, no. 17 (1996): 4159–66. http://dx.doi.org/10.1021/ja954296y.

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38

Riaño, Iker, Uxue Uria, Efraím Reyes, Luisa Carrillo, and Jose L. Vicario. "Organocatalytic Transannular Approach to Stereodefined Bicyclo[3.1.0]hexanes." Journal of Organic Chemistry 83, no. 7 (2018): 4180–89. http://dx.doi.org/10.1021/acs.joc.8b00165.

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39

Gratia, Synthia, Kathryn Mosesohn, and Steven T. Diver. "Highly Selective Ring Expansion of Bicyclo[3.1.0]hexenes." Organic Letters 18, no. 20 (2016): 5320–23. http://dx.doi.org/10.1021/acs.orglett.6b02641.

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40

Obara, Robert, Jacek Łyczko, and Antoni Szumny. "Enantioselective Lactonization of 3,3,6-Trimethyl-4(E)-heptenoic Acid Esters." Journal of Chemistry 2018 (December 2, 2018): 1–8. http://dx.doi.org/10.1155/2018/6135281.

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Studies on the use of lactonization in the asymmetric synthesis of 6,6-dimethyl-4-isopropyl-3-oxabicyclo[3.1.0]hexan-2-one were described. An asymmetrically induced lactonization reaction was performed on 3,3,6-trimethyl-4(E)-heptenoic acid esters (1) and enantiomerically pure alcohols such as (−)-menthol (a), (+)-menthol (b), (−)-borneol (c), (+)-isomenthol (d), (−)-isopinocampheol (e), and (S)-(−)-1-(2-bornylphenyl)-1-ethanol (f). The enantiomerically pure alcohols that were used as ancillary chiral substances were characterized by markedly different values of induction power; menthol (a, b)

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41

Li, Jing, Todd L. Lowary, and Michael J. Ferguson. "2-(Methoxymethoxy)-1-(4-oxobicyclo[3.1.0]hexan-1-yl)ethyl 4-nitrobenzoate." Acta Crystallographica Section E Structure Reports Online 64, no. 1 (2007): o329. http://dx.doi.org/10.1107/s160053680706686x.

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42

Wiberg, Kenneth B., Steven R. Kass, and K. C. Bishop. "Electrophilic cleavage of cyclopropanes. Acetolysis of bicyclo[2.1.0]pentane and bicyclo[3.1.0]hexane." Journal of the American Chemical Society 107, no. 4 (1985): 996–1002. http://dx.doi.org/10.1021/ja00290a041.

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43

HROVAT, D. A., A. RAUK, T. S. SORENSEN, H. K. POWELL, and W. T. BORDEN. "ChemInform Abstract: Ring Opening of Bicyclo(n.1.0)alkanones to 2-Cycloalkanone-1,3-diyls. Why Does Oxyallyl Diradical Formation Require Less Energy from Bicyclo( 3.1.0)hexan-6-ones than from Bicyclo(1.1.0)butan-2-ones?" ChemInform 27, no. 34 (2010): no. http://dx.doi.org/10.1002/chin.199634010.

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44

Luzung, Michael R., Jordan P. Markham, and F. Dean Toste. "Catalaytic Isomerization of 1,5-Enynes to Bicyclo[3.1.0]hexenes." Journal of the American Chemical Society 126, no. 35 (2004): 10858–59. http://dx.doi.org/10.1021/ja046248w.

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45

Puranik, V. G. "Structure of cis-4-acetyl-6,6-dimethyl-3-oxabicyclo[3.1.0]hexan-2-one." Acta Crystallographica Section C Crystal Structure Communications 44, no. 1 (1988): 163–64. http://dx.doi.org/10.1107/s0108270187009132.

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46

Milewska, Maria J., Maria Gdaniec, and Tadeusz Poloński. "Stereochemistry and chiroptical spectra of 3-azabicyclo[3.1.0]hexan-2-ones and thiones." Tetrahedron: Asymmetry 8, no. 8 (1997): 1267–73. http://dx.doi.org/10.1016/s0957-4166(97)00111-0.

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47

Quast, Helmut, Josef Walter Stawitz, and Bodo Mueller. "ChemInform Abstract: Synthesis, Reactions, and Rearrangements of 2,4-Diazabicyclo[3.1.0]hexan-3-ones." ChemInform 44, no. 7 (2013): no. http://dx.doi.org/10.1002/chin.201307101.

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48

Yin, Jianguo, and W. M. Jones. "Transition-metal complexes of bicyclo[3.1.0]hex-5-ene and bicyclo[4.1.0]hept-6-ene." Organometallics 12, no. 6 (1993): 2013–14. http://dx.doi.org/10.1021/om00030a008.

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49

Kozhushkov, Sergei I., Rainer Langer, Dmitrii S. Yufit, et al. "Novel Liquid Crystalline Compounds Containing Bicyclo[3.1.0]hexane Core Units." European Journal of Organic Chemistry 2004, no. 2 (2004): 289–303. http://dx.doi.org/10.1002/ejoc.200300448.

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50

Bonnaud, Bernard, Philippe Funes, Nathalie Jubault та Bernard Vacher. "Preparation of Conformationally Constrained α2 Antagonists:The Bicyclo[3.1.0]hexane Approach". European Journal of Organic Chemistry 2005, № 15 (2005): 3360–69. http://dx.doi.org/10.1002/ejoc.200500143.

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