Research Article: (Z)-6-Hy­droxy-1a,5-dimethyl-8-[(morpholin-4-yl)meth­yl]-2,3,6,7,7a,8,10a,10b-octa­hydro­oxireno[2′,3′:9,10]cyclo­deca­[1,2-b]furan-9(1aH)-one

Date Published: July 01, 2011

Publisher: International Union of Crystallography

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


The title compound, C19H29NO5, was synthesized from 9α-hy­droxy­parthenolide (9α-hy­droxy-4,8-dimethyl-12-methylen-3,14-dioxatricyclo­[,4]tetra­dec-7-en-13-one), which was isolated from the chloro­form extract of the aerial parts of Anvillea radiata. The mol­ecule is built up from two fused five- and ten-membered rings with the (morpholin-4-yl)methyl group as a substituent. The five-membered lactone ring has an envelope conformation, whereas the ten-membered and the morpholine rings display approximate chair–chair and chair conformations, respectively. The dihedral angle between the ten-membered ring and the lactone ring is 27.93 (6)°. The crystal structure is stabilized by weak inter­molecular C—H⋯O hydrogen-bond inter­actions. An intra­molecular O—H⋯N hydrogen bond also occurs.

Partial Text

For background to the medicinal uses of the plant Anvillea radiata, see: Abdel Sattar et al. (1996 ▶); Bellakhdar (1997 ▶); El Hassany et al. (2004 ▶); Qureshi et al. (1990 ▶). For the reactivity of this sesquiterpene see: Der-Ren et al. (2006 ▶). For ring puckering parameters, see: Cremer & Pople (1975 ▶).




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