4α-chloro-5α-androstan-3β-ol-17-one | 65370-36-7

• 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: 4α-chloro-5α-androstan-3β-ol-17-one
• 英文别名: (S)-4α-Chlor-5α-androstan-3β-ol-17-on；4α-Chlor-5α-androstan-3β-ol-17-on；(3S,4S,5R,8R,9S,10R,13S,14S)-4-chloro-3-hydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthren-17-one
• CAS: 65370-36-7
• 化学式: C₁₉H₂₉ClO₂
• 分子量: 324.891
• InChiKey: KQBJWRFVCBUMGI-ATMNEXLDSA-N

物化性质

• 沸点：
  451.3±45.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4α-chloro-5α-androstan-3β-ol-17-one 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 生成 (3aS,3bR,5aS,6R,8aR,8bS,10aS)-8a,10a-dimethyl-1-oxo-3,3a,3b,4,5,5a,6,7,8,8b,9,10-dodecahydro-2H-indeno[5,4-e]indene-6-carbaldehyde
  参考文献：
  名称：

  Dmochowska-Gladysz,J.; Siewinski,A., Bulletin de l'Academie Polonaise des Sciences, Serie des Sciences Chimiques, 1977, vol. 25, p. 581 - 587

  摘要：

  DOI：
• 作为产物：
  描述：

  氯司替勃 在 potato dextrose broth medium 作用下， 以 乙醇 为溶剂， 反应 96.0h， 以15%的产率得到4α-chloro-5α-androstan-3β-ol-17-one
  参考文献：
  名称：

  Formation of 5α steroids by biotranformation involving the 5α-reductase activity of Penicillium decumbens

  摘要：

  The biotransformation of a series of Delta(4)-3-ketosteroids by the fungus Penicillium decumbens ATCC 10436 has been investigated. Conversion to the 5 alpha-dihydrosteroid was observed for several substrates of the androstene and pregnene series: the reaction is tolerant of non-polar subdituents (Cl and CH3) at C-4 of the substrate, but does not occur in the presence of a 4-hydroxyl group, or with additional unsaturation at the Delta(1) or Delta(6) positions. A-nor-, B-nor-, 3-deoxy-, and 3,5-cycloandrostanes are not reduced, but 6-methylenetestosterone is converted to a 6-methylene-5 alpha-dihydro derivative. Several biotransformations are reported which involve oxidoreductase activity at C-3 and/or C-17, either concomitant or independent of Delta(4) reduction: the substrate specificity of the oxidoreductase processes has been examined and defined by the use of 3 alpha-hydroxy, 3 beta-hydroxy, 3-keto, and 17 beta-hydroxy-17-keto substituted steroids. In this way, the existence in P. decumbens of 3 beta-hydroxy-3-keto and 17 beta-hydroxy-17-keto oxidoreductases has been demonstrated.

  DOI：

  10.1016/0039-128x(94)90020-5