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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...
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/PMC3379221/ https://www.ncbi.nlm.nih.gov/pubmed/22719419 http://dx.doi.org/10.1107/S1600536812018570 |
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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 |
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