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. 2010 Jan 16;66(Pt 2):o356-7.
doi: 10.1107/S1600536810001169.

(1R,3aR,5aS,6S,8aR,8bR,9aS)-1-Hydr-oxy-6-isopropyl-1,3a,5a-trimethyl-perhydro-cyclo-penta-[a]cyclo-propa[i]naphthalen-4-one

Iván Brito, Jorge Bórquez, Luis Alberto Loyola, Michael Bolte, Joselyn Albanez

(1R,3aR,5aS,6S,8aR,8bR,9aS)-1-Hydr-oxy-6-isopropyl-1,3a,5a-trimethyl-perhydro-cyclo-penta-[a]cyclo-propa[i]naphthalen-4-one

Iván Brito et al. Acta Crystallogr Sect E Struct Rep Online. .

Abstract

The title compound (also know as azorellanone), C(20)H(32)O(2), is built up from three fused carbocycles, one five-membered ring and two six-membered rings. The five membered-ring has an envelope conformation, whereas the six-membered rings have a distorted half-chair and a twist-boat conformation. In the crystal, mol-ecules are linked by O-H⋯O inter-actions into zigzag chains with graph-set notation C(8) along [010]. The absolute configuration was assigned on the basis of earlier chemical studies.

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Figures

Fig. 1.
Fig. 1.
Molecular structure of the title compound with displacement ellipsoids at the 50% probability level showing atom-labelling scheme.
Fig. 2.
Fig. 2.
Part of the crystal structure of (I), showing the formation of a C(8) chain along [010]. Hydrogen bond shown as dashed lines.
See this image and copyright information in PMC

References

    1. Allen, F. H. (2002). Acta Cryst. B58, 380–388. - PubMed
    1. Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl.34, 1555–1573.
    1. Borquez, J., Loyola, L. A., Morales, G., San-Martín, A., Roldan, R., Marquez, N. & Muñoz, E. (2007). Phytother. Res.21, 1082–1086. - PubMed
    1. Chiaramello, A. I., Ardanaz, C. E., García, E. E. & Rossomando, P. C. (2003). Phytochemistry, 63, 883–886. - PubMed
    1. Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc.97, 1354–1358.