3β-Acetoxy-5α,17α-pregn-14-en-20-one | 24663-10-3

• 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-Acetoxy-5α,17α-pregn-14-en-20-one
• 英文别名: 3β-Acetoxy-20-oxo-5α.17α-pregnen-14；[(3S,5S,8R,9S,10S,13R,17R)-17-acetyl-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate
• CAS: 24663-10-3
• 化学式: C₂₃H₃₄O₃
• 分子量: 358.521
• InChiKey: JUAATDNYHZEPLN-XWJVLSSFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3β-Acetoxy-5α,17α-pregn-14-en-20-one 在 吡啶 、 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 48.0h， 生成 3β-Acetoxy-5α-pregn-14-en-20-one
  参考文献：
  名称：

  Simbi, Lumbu; Van Heerden, Fanie R., Journal of the Chemical Society. Perkin transactions I, 1997, # 3, p. 269 - 273

  摘要：

  DOI：
• 作为产物：
  描述：

  14-hydroxy-3β-acetoxy-5α.14β.17βH-pregnanone-(20) 在 吡啶 、 氯化亚砜 作用下， 生成 3β-Acetoxy-5α,17α-pregn-14-en-20-one
  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

文献信息

• 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.
• Simbi, Lumbu; Van Heerden, Fanie R., Journal of the Chemical Society. Perkin transactions I, 1997, # 3, p. 269 - 273
  作者：Simbi, Lumbu、Van Heerden, Fanie R.

  DOI：——

  日期：——