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12-{[4-(4-Bromo­phen­yl)piperazin-1-yl]meth­yl}-9α-hy­droxy-4,8-dimethyl-3,14-dioxatri­cyclo­[9.3.0.0(2,4)]tetra­dec-7-en-13-one

The title compound, C(25)H(33)BrN(2)O(4), was synthesized from 9α-hy­droxy­parthenolide (9α-hy­droxy-4,8-dimethyl-12-methylen-3,14-dioxa-tri­cyclo­[9.3.0.0(2,4)]tetra­dec-7-en-13-one), which was isolated from the chloro­form extract of the aerial parts of Anvillea radiata. The mol­ecule is built up...

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Detalles Bibliográficos
Autores principales: Loubidi, Mohamed, Benharref, Ahmed, El Ammari, Lahcen, Saadi, Mohamed, Berraho, Moha
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2014
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3998562/
https://www.ncbi.nlm.nih.gov/pubmed/24826186
http://dx.doi.org/10.1107/S1600536814006473
Descripción
Sumario:The title compound, C(25)H(33)BrN(2)O(4), was synthesized from 9α-hy­droxy­parthenolide (9α-hy­droxy-4,8-dimethyl-12-methylen-3,14-dioxa-tri­cyclo­[9.3.0.0(2,4)]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 an additional ep­oxy ring system and a bromo­phenyl­piperazine group as a substituent. The ten-membered ring adopts an approximate chair–chair–chair conformation, while the piperazine ring displays a chair conformation and the five-membered ring shows an envelope conformation with the C atom closest to the hy­droxy group forming the flap. An intra­molecular O—H⋯N hydrogen bond stabilizes the mol­ecular conformation. The crystal packing features C—H⋯O hydrogen bonds, which link the mol­ecules into zigzag chains running along the b-axis direction.