Research Article: Methyl 2-(1a,4a-dimethyl-2,8-dioxo-2,3,4,4a,5,6,7,8-octa­hydro-1aH-1-oxacyclo­propa[d]naphthalen-7-yl)acrylate

Date Published: February 01, 2012

Publisher: International Union of Crystallography

Author(s): Mohamed Tebbaa, Ahmed Benharref, Jean Claude Daran, Fouad Mellouki, Moha Berraho.


The title compound, C16H20O5, was synthesized from ilicic acid [2-(8-hy­droxy-4a,8-dimethyl­deca­hydro­naphthalen-2-yl)acrylic acid], which was isolated from the chloro­form extract of the aerial part of Inula viscose (L) Aiton [or Dittrichia viscosa­ (L) Greuter]. The molecule is built up from two fused six-membered rings, the epoxidized six-membered ring adopts a half-chair conformation while the other ring displays a perfect chair conformation. The crystal structure features C—H⋯O hydrogen bonds.

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For medicinal background to Inula Viscosa­ (L) Aiton [or Dittrichia Viscosa­ (L) Greuter], see: Shtacher & Kasshman (1970 ▶); Chiappini et al. (1982 ▶); Azoulay et al. (1986 ▶); Bohlman et al. (1977 ▶); Ceccherelli et al. (1988 ▶); Geissman & Toribio (1967 ▶) For the synthesis, see: Barrero et al. (2009 ▶); Tebbaa et al. (2011 ▶). For conformational analysis, see: Cremer & Pople (1975 ▶).