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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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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
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author Loubidi, Mohamed
Benharref, Ahmed
El Ammari, Lahcen
Saadi, Mohamed
Berraho, Moha
author_facet Loubidi, Mohamed
Benharref, Ahmed
El Ammari, Lahcen
Saadi, Mohamed
Berraho, Moha
author_sort Loubidi, Mohamed
collection PubMed
description 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.
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spelling pubmed-39985622014-05-13 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 Loubidi, Mohamed Benharref, Ahmed El Ammari, Lahcen Saadi, Mohamed Berraho, Moha Acta Crystallogr Sect E Struct Rep Online Organic Papers 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. International Union of Crystallography 2014-03-29 /pmc/articles/PMC3998562/ /pubmed/24826186 http://dx.doi.org/10.1107/S1600536814006473 Text en © Loubidi et al. 2014 http://creativecommons.org/licenses/by/2.0/uk/ This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
spellingShingle Organic Papers
Loubidi, Mohamed
Benharref, Ahmed
El Ammari, Lahcen
Saadi, Mohamed
Berraho, Moha
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
title 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
title_full 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
title_fullStr 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
title_full_unstemmed 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
title_short 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
title_sort 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
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3998562/
https://www.ncbi.nlm.nih.gov/pubmed/24826186
http://dx.doi.org/10.1107/S1600536814006473
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