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9-Hydroxy-4,8-dimethyl-12-(piperidin-1-ylmethyl)-3,14-dioxatricyclo[9.3.0.0(2,4)]tetradec-7-en-13-one
The title compound, C(20)H(31)NO(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 f...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2011
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3201218/ https://www.ncbi.nlm.nih.gov/pubmed/22058816 http://dx.doi.org/10.1107/S1600536811038803 |
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author | Moumou, Mohamed Benharref, Ahmed Daran, Jean-Claude Elhakmaoui, Ahmed Berraho, Moha |
author_facet | Moumou, Mohamed Benharref, Ahmed Daran, Jean-Claude Elhakmaoui, Ahmed Berraho, Moha |
author_sort | Moumou, Mohamed |
collection | PubMed |
description | The title compound, C(20)H(31)NO(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 fused five-and ten-membered rings with the pipyridin-1-yl-methyl group as a substituent. The ten-membered ring adopts an approximate chair–chair conformation, while the six-membered ring display a chair conformation and the five-membered ring an envelope conformation with the C(H)–C–C(H) atom at the flap. The dihedral angle between the ten-membered ring and the lactone ring is 21.7 (4)°. The molecular conformation is stabilized by an O—H⋯N hydrogen bond and the crystal structure is stabilized by weak intermolecular C—H⋯O interactions. |
format | Online Article Text |
id | pubmed-3201218 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2011 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-32012182011-11-06 9-Hydroxy-4,8-dimethyl-12-(piperidin-1-ylmethyl)-3,14-dioxatricyclo[9.3.0.0(2,4)]tetradec-7-en-13-one Moumou, Mohamed Benharref, Ahmed Daran, Jean-Claude Elhakmaoui, Ahmed Berraho, Moha Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound, C(20)H(31)NO(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 fused five-and ten-membered rings with the pipyridin-1-yl-methyl group as a substituent. The ten-membered ring adopts an approximate chair–chair conformation, while the six-membered ring display a chair conformation and the five-membered ring an envelope conformation with the C(H)–C–C(H) atom at the flap. The dihedral angle between the ten-membered ring and the lactone ring is 21.7 (4)°. The molecular conformation is stabilized by an O—H⋯N hydrogen bond and the crystal structure is stabilized by weak intermolecular C—H⋯O interactions. International Union of Crystallography 2011-09-30 /pmc/articles/PMC3201218/ /pubmed/22058816 http://dx.doi.org/10.1107/S1600536811038803 Text en © Moumou et al. 2011 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 Elhakmaoui, Ahmed Berraho, Moha 9-Hydroxy-4,8-dimethyl-12-(piperidin-1-ylmethyl)-3,14-dioxatricyclo[9.3.0.0(2,4)]tetradec-7-en-13-one |
title | 9-Hydroxy-4,8-dimethyl-12-(piperidin-1-ylmethyl)-3,14-dioxatricyclo[9.3.0.0(2,4)]tetradec-7-en-13-one |
title_full | 9-Hydroxy-4,8-dimethyl-12-(piperidin-1-ylmethyl)-3,14-dioxatricyclo[9.3.0.0(2,4)]tetradec-7-en-13-one |
title_fullStr | 9-Hydroxy-4,8-dimethyl-12-(piperidin-1-ylmethyl)-3,14-dioxatricyclo[9.3.0.0(2,4)]tetradec-7-en-13-one |
title_full_unstemmed | 9-Hydroxy-4,8-dimethyl-12-(piperidin-1-ylmethyl)-3,14-dioxatricyclo[9.3.0.0(2,4)]tetradec-7-en-13-one |
title_short | 9-Hydroxy-4,8-dimethyl-12-(piperidin-1-ylmethyl)-3,14-dioxatricyclo[9.3.0.0(2,4)]tetradec-7-en-13-one |
title_sort | 9-hydroxy-4,8-dimethyl-12-(piperidin-1-ylmethyl)-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/PMC3201218/ https://www.ncbi.nlm.nih.gov/pubmed/22058816 http://dx.doi.org/10.1107/S1600536811038803 |
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