17α-ethoxycarbonyloxy-3-oxoandrost-4-ene-17-carbonitrile | 132639-68-0

• 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-ethoxycarbonyloxy-3-oxoandrost-4-ene-17-carbonitrile
• 英文别名: [(8R,9S,10R,13S,14S,17R)-17-cyano-10,13-dimethyl-3-oxo-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-17-yl] ethyl carbonate
• CAS: 132639-68-0
• 化学式: C₂₃H₃₁NO₄
• 分子量: 385.503
• InChiKey: ZVAOAJHHLVZEAV-JZTHCNPZSA-N

物化性质

• 沸点：
  556.6±50.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  76.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  雄烯二酮 在 四丁基氯化铵 、 sodium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 720.0h， 生成 17α-ethoxycarbonyloxy-3-oxoandrost-4-ene-17-carbonitrile
  参考文献：
  名称：

  Highly efficient synthesis of steroid-17-spiro-5'-oxazolidine-2', 4' -diones from 17-keto steroids

  摘要：

  Spiro[androst-4-en-17alpha, 5'-oxazolidine]-2', 3, 4'-trione 8-alpha and spiro]androst-4-en-17alpha, 5'-oxazolidine[-2', 3, 4', 11-tetraone 8b, two potentially bioactive spiranes, were prepared from the parent 17-ketones in four steps (64% and 49.5% yield, respectively). The key intermediates were the hydroxyimidates 5a and 5b, which easily underwent cyclization to the corresponding spirooxazolinone 4'-enol ethers when treated with alkychlorocarbonates. The respective N-amyl derivatives of the spiranes 8a and 8b were obtained with n-pentyl bromide in the presence of KF. A new method for the synthesis of steroid 17-alpha-hydroxy-17-carboxyesters and 17-alpha-hydroxy-17-carboxamides is described. Attempts to synthesize the title compounds from these products were unsuccessful.

  DOI：

  10.1016/0039-128x(90)90088-s

文献信息

• Highly efficient synthesis of steroid-17-spiro-5'-oxazolidine-2', 4' -diones from 17-keto steroids
  作者：Mauro Ginanneschi、Mario Chelli、Annamaria Papini、Gianfranco Rapi

  DOI：10.1016/0039-128x(90)90088-s

  日期：1990.11

  Spiro[androst-4-en-17alpha, 5'-oxazolidine]-2', 3, 4'-trione 8-alpha and spiro]androst-4-en-17alpha, 5'-oxazolidine[-2', 3, 4', 11-tetraone 8b, two potentially bioactive spiranes, were prepared from the parent 17-ketones in four steps (64% and 49.5% yield, respectively). The key intermediates were the hydroxyimidates 5a and 5b, which easily underwent cyclization to the corresponding spirooxazolinone 4'-enol ethers when treated with alkychlorocarbonates. The respective N-amyl derivatives of the spiranes 8a and 8b were obtained with n-pentyl bromide in the presence of KF. A new method for the synthesis of steroid 17-alpha-hydroxy-17-carboxyesters and 17-alpha-hydroxy-17-carboxamides is described. Attempts to synthesize the title compounds from these products were unsuccessful.