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

The title compound, C(26)H(36)N(2)O(5), was synthesized from 9α-hy­droxy­parthenolide (9α-hy­droxy-4,8-dimethyl-12-methyl­ene-3,14-dioxatricyclo­[9.3.0.0(2,4)]tetra­dec-7-en-13-one), wich was isolated from the chloro­form extract of the aerial parts of Anvillea radiata. The mol­ecule is built up fro...

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Autores principales: Moumou, Mohamed, Benharref, Ahmed, Daran, Jean-Claude, Mellouki, Fouad, Berraho, Moha
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2012
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3297315/
https://www.ncbi.nlm.nih.gov/pubmed/22412505
http://dx.doi.org/10.1107/S1600536812003662
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author Moumou, Mohamed
Benharref, Ahmed
Daran, Jean-Claude
Mellouki, Fouad
Berraho, Moha
author_facet Moumou, Mohamed
Benharref, Ahmed
Daran, Jean-Claude
Mellouki, Fouad
Berraho, Moha
author_sort Moumou, Mohamed
collection PubMed
description The title compound, C(26)H(36)N(2)O(5), was synthesized from 9α-hy­droxy­parthenolide (9α-hy­droxy-4,8-dimethyl-12-methyl­ene-3,14-dioxatricyclo­[9.3.0.0(2,4)]tetra­dec-7-en-13-one), wich was isolated from the chloro­form extract of the aerial parts of Anvillea radiata. The mol­ecule is built up from fused five- and ten-membered rings with the meth­oxy­phenyl­piperazine group as a substituent. The ten-membered ring adopts an approximate chair–chair conformation, while the piperazine ring displays a chair conformation and the five-membered ring a flattened envelope conformation; the C(H)—C—C(H) atoms representing the flap lie out of the mean plane through the remaining four atoms by 0.343 (3) Å. The dihedral angle between the mean planes of the ten-membered ring and the lactone ring is 18.12 (14)°. An intra­molecular O—H⋯N hydrogen bond occurs. The crystal structure features weak C—H⋯O inter­actions.
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spelling pubmed-32973152012-03-12 9α-Hy­droxy-12-{[4-(4-meth­oxy­phen­yl)piperazin-1-yl]meth­yl}-4,8-dimethyl-3,14-dioxatricyclo­[9.3.0.0(2,4)]tetra­dec-7-en-13-one Moumou, Mohamed Benharref, Ahmed Daran, Jean-Claude Mellouki, Fouad Berraho, Moha Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound, C(26)H(36)N(2)O(5), was synthesized from 9α-hy­droxy­parthenolide (9α-hy­droxy-4,8-dimethyl-12-methyl­ene-3,14-dioxatricyclo­[9.3.0.0(2,4)]tetra­dec-7-en-13-one), wich was isolated from the chloro­form extract of the aerial parts of Anvillea radiata. The mol­ecule is built up from fused five- and ten-membered rings with the meth­oxy­phenyl­piperazine group as a substituent. The ten-membered ring adopts an approximate chair–chair conformation, while the piperazine ring displays a chair conformation and the five-membered ring a flattened envelope conformation; the C(H)—C—C(H) atoms representing the flap lie out of the mean plane through the remaining four atoms by 0.343 (3) Å. The dihedral angle between the mean planes of the ten-membered ring and the lactone ring is 18.12 (14)°. An intra­molecular O—H⋯N hydrogen bond occurs. The crystal structure features weak C—H⋯O inter­actions. International Union of Crystallography 2012-02-04 /pmc/articles/PMC3297315/ /pubmed/22412505 http://dx.doi.org/10.1107/S1600536812003662 Text en © Moumou et al. 2012 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
Moumou, Mohamed
Benharref, Ahmed
Daran, Jean-Claude
Mellouki, Fouad
Berraho, Moha
9α-Hy­droxy-12-{[4-(4-meth­oxy­phen­yl)piperazin-1-yl]meth­yl}-4,8-dimethyl-3,14-dioxatricyclo­[9.3.0.0(2,4)]tetra­dec-7-en-13-one
title 9α-Hy­droxy-12-{[4-(4-meth­oxy­phen­yl)piperazin-1-yl]meth­yl}-4,8-dimethyl-3,14-dioxatricyclo­[9.3.0.0(2,4)]tetra­dec-7-en-13-one
title_full 9α-Hy­droxy-12-{[4-(4-meth­oxy­phen­yl)piperazin-1-yl]meth­yl}-4,8-dimethyl-3,14-dioxatricyclo­[9.3.0.0(2,4)]tetra­dec-7-en-13-one
title_fullStr 9α-Hy­droxy-12-{[4-(4-meth­oxy­phen­yl)piperazin-1-yl]meth­yl}-4,8-dimethyl-3,14-dioxatricyclo­[9.3.0.0(2,4)]tetra­dec-7-en-13-one
title_full_unstemmed 9α-Hy­droxy-12-{[4-(4-meth­oxy­phen­yl)piperazin-1-yl]meth­yl}-4,8-dimethyl-3,14-dioxatricyclo­[9.3.0.0(2,4)]tetra­dec-7-en-13-one
title_short 9α-Hy­droxy-12-{[4-(4-meth­oxy­phen­yl)piperazin-1-yl]meth­yl}-4,8-dimethyl-3,14-dioxatricyclo­[9.3.0.0(2,4)]tetra­dec-7-en-13-one
title_sort 9α-hy­droxy-12-{[4-(4-meth­oxy­phen­yl)piperazin-1-yl]meth­yl}-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/PMC3297315/
https://www.ncbi.nlm.nih.gov/pubmed/22412505
http://dx.doi.org/10.1107/S1600536812003662
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