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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...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2012
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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. |
format | Online Article Text |
id | pubmed-3297315 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2012 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
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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