3β,14β-Dihydroxy-5α,17α-pregnan-20-on | 24663-05-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 3β,14β-Dihydroxy-5α,17α-pregnan-20-on
• 英文别名: 3β,14-dihydroxy-5α,14β,17β^H-pregnan-20-one；3β,14-Dihydroxy-5α,14β,17β^H-pregnan-20-on；1-[(3S,5S,8R,9S,10S,13R,14S,17R)-3,14-dihydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]ethanone
• CAS: 24663-05-6
• 化学式: C₂₁H₃₄O₃
• 分子量: 334.499
• InChiKey: CIUZTBJZAMUYJU-KOWYNTSXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3β,14β-Dihydroxy-5α,17α-pregnan-20-on 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 生成 3β,14β,20ξ-Trihydroxy-5α,17α-pregnan
  参考文献：
  名称：

  [从纤维毛发菌根（Weimark）Bullock的根中得到的胡萝卜素和孕烷衍生物。糖苷和糖苷配基。322]。

  摘要：

  AbstractThe roots of Trachycalymma fimbriatum (WEIMARCK) BULLOCK contain both cardenolide and pregnaneglycosides. Elimination of 2‐deoxysugars by mild acid hydrolysis gave a mixture from which some anhydroderivatives and the following compounds could be isolated: uzarigenin (l), ascleposide = 3‐O‐(6‐deoxy‐β‐D‐allopyranosyl)‐uzarigenin (4), coroglaucigenin (6) and two pregnane derivatives (H and J). Compound H could be identified as 3β,14β‐dihydroxy5α, 17α‐pregnan‐20‐one (10). Compound J is probably a new substance, for which we tentatively assign structure 18, i.e. 3β8β,14β‐trihydroxy‐5α,17α‐pregnan‐20‐one. We suspect H and J to be artefacts produced from the corresponding 17b‐derivatives during acid hydrolysis. 17‐iso‐H is probably a precursor in the biosynthesis of uzarigenin. The cardenolides of Trachycalymma fimbriatum are the same as found in Asclepias glaucophylla, a closely related species, while the pregnane derivatives of the latter are distinctly higher hydroxylated.

  DOI：

  10.1002/hlca.19690520841
• 作为产物：
  描述：

  3b-羟基-5a-孕甾烷-16-烯-20-酮 生成 3β,14β-Dihydroxy-5α,17α-pregnan-20-on
  参考文献：
  名称：

  DE842053

  摘要：

  公开号：

文献信息

• Process of preparing 14-hydroxy steroids
  申请人：CIBA PHARM PROD INC

  公开号：US02555704A1

  公开（公告）日：1951-06-05
• Cardenolide und Pregnanderivate aus den Wurzeln vonTrachycalymma fimbriatum (WEIMARCK) BULLOCK Glykoside und Aglykone, 322. Mitteilung
  作者：R. Elber、Ek. Weiss、T. Reichstein

  DOI：10.1002/hlca.19690520841

  日期：——

  AbstractThe roots of Trachycalymma fimbriatum (WEIMARCK) BULLOCK contain both cardenolide and pregnaneglycosides. Elimination of 2‐deoxysugars by mild acid hydrolysis gave a mixture from which some anhydroderivatives and the following compounds could be isolated: uzarigenin (l), ascleposide = 3‐O‐(6‐deoxy‐β‐D‐allopyranosyl)‐uzarigenin (4), coroglaucigenin (6) and two pregnane derivatives (H and J). Compound H could be identified as 3β,14β‐dihydroxy5α, 17α‐pregnan‐20‐one (10). Compound J is probably a new substance, for which we tentatively assign structure 18, i.e. 3β8β,14β‐trihydroxy‐5α,17α‐pregnan‐20‐one. We suspect H and J to be artefacts produced from the corresponding 17b‐derivatives during acid hydrolysis. 17‐iso‐H is probably a precursor in the biosynthesis of uzarigenin. The cardenolides of Trachycalymma fimbriatum are the same as found in Asclepias glaucophylla, a closely related species, while the pregnane derivatives of the latter are distinctly higher hydroxylated.
• DE842053
  申请人：——

  公开号：——

  公开（公告）日：——