17α-Cyanomethyl-17β-hydroxy-5α-estran-3-on | 83807-33-4

• 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: 17α-Cyanomethyl-17β-hydroxy-5α-estran-3-on
• 英文别名: 17α-cyanomethyl-17-hydroxy-5α-estran-3-one；2-[(5S,8R,9R,10S,13S,14S,17R)-17-hydroxy-13-methyl-3-oxo-1,2,4,5,6,7,8,9,10,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthren-17-yl]acetonitrile
• CAS: 83807-33-4
• 化学式: C₂₀H₂₉NO₂
• 分子量: 315.456
• InChiKey: UDPNUGVTUSBARE-NQNADTQCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  61.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  17α-Cyanomethyl-17β-hydroxy-5α-estran-3-on 在 氢氧化钾 、 sodium tetrahydroborate 、 methyl azodicarboxylate 、 三苯基膦 作用下， 以 异丙醇 、 苯 为溶剂， 反应 32.0h， 生成 17α-Cyanomethyl-5α-estran-3α,17β-diol
  参考文献：
  名称：

  Hubner; Fussel; Ponsold, Pharmazie, 1984, vol. 39, # 7, p. 462 - 463

  摘要：

  DOI：
• 作为产物：
  描述：

  17α-Cyanomethyl-5α-estran-3β,17β-diol 在 chromium(VI) oxide 、 硫酸 作用下， 以 丙酮 为溶剂， 生成 17α-Cyanomethyl-17β-hydroxy-5α-estran-3-on
  参考文献：
  名称：

  Microbial transformation of 17α-cyanomethyl-17-hydroxy-4,9-estradien-3-one (STS 557) and 17α-cyanomethyl-19-nortestosterone by Mycobacterium smegmatis

  摘要：

  Microbial transformation of the new progestagen STS 557 (17 alpha-cyanomethyl-17-hydroxy-4,9-estradien-3-one) by Mycobacterium smegmatis yielded predominantly ring A-aromatized compounds: 17 alpha-cyanomethyl-1,3,5(10),9(11)-estratetraene-3, 17-diol, 17 alpha-cyanomethyl-1,3,5(10)-estratriene-3,17-diol and the corresponding 3-methyl ethers. The analogous compound without the 9(10) double bond, 17 alpha-cyanomethyl-19-nortestosterone, was transformed mainly to 5 alpha-hydrogenated metabolites: 17 alpha-cyanomethyl-17-hydroxy-5 alpha-estran-3-one, 17 alpha-cyanomethyl-17-hydroxy-5 alpha-1-estren-3-one, 17 alpha-cyanomethyl-5 alpha-estrane-3 alpha, 17-diol, and 17 alpha-cyanomethyl-5 alpha-estrane-3 beta, 17-diol. From these results, it is concluded that 4,9-dien-3-oxo compounds are not substrates for enzymatic 5 alpha-hydrogenation.

  DOI：

  10.1016/0039-128x(82)90064-2