Cargando…

14,15-Didehydro­hellebrigenin

The title compound, C(24)H(30)O(5), is the didehydro product of the steroid hellebrigenin (systematic name: 3β,5,14-trihy­droxy-19-oxo-5β-bufa-20,22-dienolide). It consists of three cyclo­hexane rings (A, B and C), a five-membered ring (D) and a six-membered lactone ring (E). The stereochemistry of...

Descripción completa

Detalles Bibliográficos
Autores principales: Yu, Tong, Tian, Hai-Yan, Yuan, Xiao-Feng, Hu, Shu-Zhi, Jiang, Ren-Wang
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2012
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3379221/
https://www.ncbi.nlm.nih.gov/pubmed/22719419
http://dx.doi.org/10.1107/S1600536812018570
_version_ 1782236150098821120
author Yu, Tong
Tian, Hai-Yan
Yuan, Xiao-Feng
Hu, Shu-Zhi
Jiang, Ren-Wang
author_facet Yu, Tong
Tian, Hai-Yan
Yuan, Xiao-Feng
Hu, Shu-Zhi
Jiang, Ren-Wang
author_sort Yu, Tong
collection PubMed
description The title compound, C(24)H(30)O(5), is the didehydro product of the steroid hellebrigenin (systematic name: 3β,5,14-trihy­droxy-19-oxo-5β-bufa-20,22-dienolide). It consists of three cyclo­hexane rings (A, B and C), a five-membered ring (D) and a six-membered lactone ring (E). The stereochemistry of the ring junctions are A/B cis, B/C trans and C/D cis. Cyclo­hexane rings A, B and C have normal chair conformations. The five-membered ring D with the C=C bond adopts an envelope conformation. Lactone ring E is essentially planar with a mean derivation of 0.006 (4) Å and is β-oriented at the C atom of ring D to which it is attached. There is an O—H⋯O hydrogen bond in the mol­ecule involving the hy­droxy groups. In the crystal, O—H⋯O hydrogen bonds link the mol­ecules into chains propagating along [010]. The chains are linked by C—H⋯O contacts into a three-dimensional network.
format Online
Article
Text
id pubmed-3379221
institution National Center for Biotechnology Information
language English
publishDate 2012
publisher International Union of Crystallography
record_format MEDLINE/PubMed
spelling pubmed-33792212012-06-20 14,15-Didehydro­hellebrigenin Yu, Tong Tian, Hai-Yan Yuan, Xiao-Feng Hu, Shu-Zhi Jiang, Ren-Wang Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound, C(24)H(30)O(5), is the didehydro product of the steroid hellebrigenin (systematic name: 3β,5,14-trihy­droxy-19-oxo-5β-bufa-20,22-dienolide). It consists of three cyclo­hexane rings (A, B and C), a five-membered ring (D) and a six-membered lactone ring (E). The stereochemistry of the ring junctions are A/B cis, B/C trans and C/D cis. Cyclo­hexane rings A, B and C have normal chair conformations. The five-membered ring D with the C=C bond adopts an envelope conformation. Lactone ring E is essentially planar with a mean derivation of 0.006 (4) Å and is β-oriented at the C atom of ring D to which it is attached. There is an O—H⋯O hydrogen bond in the mol­ecule involving the hy­droxy groups. In the crystal, O—H⋯O hydrogen bonds link the mol­ecules into chains propagating along [010]. The chains are linked by C—H⋯O contacts into a three-dimensional network. International Union of Crystallography 2012-05-05 /pmc/articles/PMC3379221/ /pubmed/22719419 http://dx.doi.org/10.1107/S1600536812018570 Text en © Yu 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
Yu, Tong
Tian, Hai-Yan
Yuan, Xiao-Feng
Hu, Shu-Zhi
Jiang, Ren-Wang
14,15-Didehydro­hellebrigenin
title 14,15-Didehydro­hellebrigenin
title_full 14,15-Didehydro­hellebrigenin
title_fullStr 14,15-Didehydro­hellebrigenin
title_full_unstemmed 14,15-Didehydro­hellebrigenin
title_short 14,15-Didehydro­hellebrigenin
title_sort 14,15-didehydro­hellebrigenin
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3379221/
https://www.ncbi.nlm.nih.gov/pubmed/22719419
http://dx.doi.org/10.1107/S1600536812018570
work_keys_str_mv AT yutong 1415didehydrohellebrigenin
AT tianhaiyan 1415didehydrohellebrigenin
AT yuanxiaofeng 1415didehydrohellebrigenin
AT hushuzhi 1415didehydrohellebrigenin
AT jiangrenwang 1415didehydrohellebrigenin