Research Article: 10α-Hy­droxy-13-{[4-(2-hy­droxy­phen­yl)piperazin-1-yl]meth­yl}-4,9-dimethyl-3,8,15-trioxatetra­cyclo­[,4.07,9]penta­decan-14-one

Date Published: May 01, 2012

Publisher: International Union of Crystallography

Author(s): Mohamed Moumou, Ahmed Benharref, Lahcen El Ammari, Mina Adil, Moha Berraho.


The title compound, C25H34N2O6, was synthesized from 9α-hy­droxy­parthenolide (9α-hy­droxy-4,8-dimethyl-12-methyl­ene-3,14-dioxatricyclo­[,4]tetra­dec-7-en-13-one), which was isolated from the chloro­form extract of the aerial parts of Anvillea radiata. The ten-membered ring adopts an approximate chair–chair conformation, while the piperazine ring displays a near regular chair conformation and the five-membered ring an envelope conformation with the C atom closest to the hy­droxy group forming the flap. The mol­ecular conformation is stabilized by an O—H⋯N hydrogen bond, which generates an S(7) loop, and the crystal structure features weak C—H⋯O inter­actions.

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For background to the medicinal uses of the plant Anvillea adiata, see: Abdel Sattar et al. (1996 ▶); El Hassany et al. (2004 ▶); Qureshi et al.(1990 ▶). For the reactivity of this sesquiterpene, see: Hwang et al. (2006 ▶); Neukirch et al. (2003 ▶); Neelakantan et al. (2009 ▶). For ring puckering parameters, see: Cremer & Pople (1975 ▶). For the synthesis, see: Moumou et al. (2010 ▶).