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(Z)-6-Hydroxy-1a,5-dimethyl-8-[(morpholin-4-yl)methyl]-2,3,6,7,7a,8,10a,10b-octahydrooxireno[2′,3′:9,10]cyclodeca[1,2-b]furan-9(1aH)-one
The title compound, C(19)H(29)NO(5), was synthesized from 9α-hydroxyparthenolide (9α-hydroxy-4,8-dimethyl-12-methylen-3,14-dioxatricyclo[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...
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/PMC3151749/ https://www.ncbi.nlm.nih.gov/pubmed/21837095 http://dx.doi.org/10.1107/S1600536811022616 |
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author | Moumou, Mohamed Benharref, Ahmed Berraho, Moha El Ammari, Lahcen Akssira, Mohamed Elhakmaoui, Ahmed |
author_facet | Moumou, Mohamed Benharref, Ahmed Berraho, Moha El Ammari, Lahcen Akssira, Mohamed Elhakmaoui, Ahmed |
author_sort | Moumou, Mohamed |
collection | PubMed |
description | The title compound, C(19)H(29)NO(5), was synthesized from 9α-hydroxyparthenolide (9α-hydroxy-4,8-dimethyl-12-methylen-3,14-dioxatricyclo[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 the (morpholin-4-yl)methyl group as a substituent. The five-membered lactone ring has an envelope conformation, whereas the ten-membered and the morpholine rings display approximate chair–chair and chair conformations, respectively. The dihedral angle between the ten-membered ring and the lactone ring is 27.93 (6)°. The crystal structure is stabilized by weak intermolecular C—H⋯O hydrogen-bond interactions. An intramolecular O—H⋯N hydrogen bond also occurs. |
format | Online Article Text |
id | pubmed-3151749 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2011 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-31517492011-08-11 (Z)-6-Hydroxy-1a,5-dimethyl-8-[(morpholin-4-yl)methyl]-2,3,6,7,7a,8,10a,10b-octahydrooxireno[2′,3′:9,10]cyclodeca[1,2-b]furan-9(1aH)-one Moumou, Mohamed Benharref, Ahmed Berraho, Moha El Ammari, Lahcen Akssira, Mohamed Elhakmaoui, Ahmed Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound, C(19)H(29)NO(5), was synthesized from 9α-hydroxyparthenolide (9α-hydroxy-4,8-dimethyl-12-methylen-3,14-dioxatricyclo[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 the (morpholin-4-yl)methyl group as a substituent. The five-membered lactone ring has an envelope conformation, whereas the ten-membered and the morpholine rings display approximate chair–chair and chair conformations, respectively. The dihedral angle between the ten-membered ring and the lactone ring is 27.93 (6)°. The crystal structure is stabilized by weak intermolecular C—H⋯O hydrogen-bond interactions. An intramolecular O—H⋯N hydrogen bond also occurs. International Union of Crystallography 2011-06-18 /pmc/articles/PMC3151749/ /pubmed/21837095 http://dx.doi.org/10.1107/S1600536811022616 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 Berraho, Moha El Ammari, Lahcen Akssira, Mohamed Elhakmaoui, Ahmed (Z)-6-Hydroxy-1a,5-dimethyl-8-[(morpholin-4-yl)methyl]-2,3,6,7,7a,8,10a,10b-octahydrooxireno[2′,3′:9,10]cyclodeca[1,2-b]furan-9(1aH)-one |
title | (Z)-6-Hydroxy-1a,5-dimethyl-8-[(morpholin-4-yl)methyl]-2,3,6,7,7a,8,10a,10b-octahydrooxireno[2′,3′:9,10]cyclodeca[1,2-b]furan-9(1aH)-one |
title_full | (Z)-6-Hydroxy-1a,5-dimethyl-8-[(morpholin-4-yl)methyl]-2,3,6,7,7a,8,10a,10b-octahydrooxireno[2′,3′:9,10]cyclodeca[1,2-b]furan-9(1aH)-one |
title_fullStr | (Z)-6-Hydroxy-1a,5-dimethyl-8-[(morpholin-4-yl)methyl]-2,3,6,7,7a,8,10a,10b-octahydrooxireno[2′,3′:9,10]cyclodeca[1,2-b]furan-9(1aH)-one |
title_full_unstemmed | (Z)-6-Hydroxy-1a,5-dimethyl-8-[(morpholin-4-yl)methyl]-2,3,6,7,7a,8,10a,10b-octahydrooxireno[2′,3′:9,10]cyclodeca[1,2-b]furan-9(1aH)-one |
title_short | (Z)-6-Hydroxy-1a,5-dimethyl-8-[(morpholin-4-yl)methyl]-2,3,6,7,7a,8,10a,10b-octahydrooxireno[2′,3′:9,10]cyclodeca[1,2-b]furan-9(1aH)-one |
title_sort | (z)-6-hydroxy-1a,5-dimethyl-8-[(morpholin-4-yl)methyl]-2,3,6,7,7a,8,10a,10b-octahydrooxireno[2′,3′:9,10]cyclodeca[1,2-b]furan-9(1ah)-one |
topic | Organic Papers |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3151749/ https://www.ncbi.nlm.nih.gov/pubmed/21837095 http://dx.doi.org/10.1107/S1600536811022616 |
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