Russian Journal of Organic Chemistry

, Volume 46, Issue 12, pp 1786–1789 | Cite as

Hydrogenation and conformational analysis of (1R,2R,6S)-3-methyl-6-(1-methylethenyl)cyclohex-3-ene-1,2-diol

  • O. V. Ardashov
  • A. M. Genaev
  • I. V. Il’ina
  • D. V. Korchagina
  • K. P. Volcho
  • N. F. Salakhutdinov
Article

Abstract

Hydrogenation of (1R,2R,6S)-3-methyl-6-(1-methylethenyl)cyclohex-3-ene-1,2-diol was studied. Nickel chloride-sodium tetrahydridoborate system turned out to selectively reduce the double bond in the isopropenyl group. The results of conformational analysis of (1R,2R,6S)-3-methyl-6-(1-methylethenyl)cyclohex-3-ene-1,2-diol and its partly and completely hydrogenated derivatives were in a good agreement with the NMR data.

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References

  1. 1.
    Tolstikova, T.G., Pavlova, A.V., Dolgikh, M.P., Il’ina, I.V., Ardashov, O.V., Volcho, K.P., Salakhutdinov, N.F., and Tolstikov, G.A., Dokl. Ross. Akad. Nauk, Fiziol., 2009, vol. 429, p. 139.Google Scholar
  2. 2.
    Il’ina, I.V., Volcho, K.P., Korchagina, D.V., Barkhash, V.A., and Salakhutdinov, N.F., Helv. Chim. Acta, 2007, vol. 90, p. 353; Ardashov, O.V., Il’ina, I.V., Korchagina, D.V., Volcho, K.P., and Salakhutdinov, N.F., Mendeleev Commun., 2007, vol. 17, p. 303.CrossRefGoogle Scholar
  3. 3.
    Saxena, I., Borah, R., and Sarma, J.C., J. Chem. Soc., Perkin Trans. 1, 2000, p. 503.Google Scholar
  4. 4.
    Sarma, J.C. and Sharma, R.P., Chem. Ind. (London), 1987, p. 764.Google Scholar
  5. 5.
    Seltzman, H.H. and Berrang, B.D., Tetrahedron Lett., 1993, vol. 34, p. 3083.CrossRefGoogle Scholar
  6. 6.
    Brown, C.A., J. Org. Chem., 1970, vol. 35, p. 1900.CrossRefGoogle Scholar
  7. 7.
    Molecular Drug Properties: Measurement and Prediction, Mannhold, R., Ed., Weinheim: Wiley, 2008, p. 502; Keserü, G.M. and Kolossváry, I., Molecular Mechanics and Conformational Analysis in Drug Design, Oxford: Blackwell Science, 1999, p. 176; Structure-Based Drug Design: Experimental and Computational Approaches, Codding, P.W., Ed., Dordrecht: Kluwer Academic, 1998.Google Scholar
  8. 8.
    Perola, E. and Charifson, P.S., J. Med. Chem., 2004, vol. 47, p. 2499.CrossRefGoogle Scholar
  9. 9.
    Repinskaya, I.B. and Shvartsberg, M.S., Izbrannye metody sinteza organicheskikh soedinenii (Selected Methods of Synthesis of Organic Compounds), Novosibirsk: Novosib. Gos. Univ., 2000, p. 284.Google Scholar
  10. 10.
    Imre, G., Jakli, I., Kalaszi, A., and Farkas, O., Advanced Automatic Generation of 3D Molecular Structures. 1st European Chemistry Congress, Budapest, Hungary, August 27–31, 2006.Google Scholar
  11. 11.
    Chang, C. and Gilson, M.K., J. Comput. Chem., 2003, vol. 24, p. 1987.CrossRefGoogle Scholar
  12. 12.
    Ren, P. and Ponder, J.W., J. Phys. Chem. B, 2003, vol. 107, p. 5933.CrossRefGoogle Scholar
  13. 13.
    Rocha, G.B., Freire, R.O., Simas, A.M., and Stewart, J.J.P., J. Comput. Chem., 2006, vol. 27, p. 1101.CrossRefGoogle Scholar
  14. 14.
    Stewart, J.J.P., MOPAC2009, Colorado Springs, CO, USA: Stewart Computational Chemistry, 2008; http://Open-MOPAC.net.Google Scholar
  15. 15.
    Perdew, J.P., Burke, K., and Ernzerhof, M., Phys. Rev. Lett., 1996, vol. 77, p. 3865.CrossRefGoogle Scholar
  16. 16.
    Laikov, D.N., Chem. Phys. Lett., 2005, vol. 416, p. 116.CrossRefGoogle Scholar
  17. 17.
    Laikov, D.N., Chem. Phys. Lett., 1997, vol. 281, p. 151; Laikov, D.N. and Ustynyuk, Yu.A., Izv. Ross. Akad. Nauk, Ser. Khim., 2005, p. 804.CrossRefGoogle Scholar

Copyright information

© Pleiades Publishing, Ltd. 2010

Authors and Affiliations

  • O. V. Ardashov
    • 1
  • A. M. Genaev
    • 1
  • I. V. Il’ina
    • 1
  • D. V. Korchagina
    • 1
  • K. P. Volcho
    • 1
  • N. F. Salakhutdinov
    • 1
  1. 1.Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian DivisionRussian Academy of SciencesNovosibirskRussia

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