3,11-dioxo-17α-hydroxyandrost-4-ene-17-carbonitrile | 132639-69-1

• 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: 3,11-dioxo-17α-hydroxyandrost-4-ene-17-carbonitrile
• 英文别名: (8S,9S,10R,13S,14S,17R)-17-hydroxy-10,13-dimethyl-3,11-dioxo-1,2,6,7,8,9,12,14,15,16-decahydrocyclopenta[a]phenanthrene-17-carbonitrile
• CAS: 132639-69-1
• 化学式: C₂₀H₂₅NO₃
• 分子量: 327.423
• InChiKey: JHNKMSMCNITKIH-GECNCUIPSA-N

物化性质

• 熔点：
  203-205 °C
• 沸点：
  543.7±50.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  24
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  78.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,11-dioxo-17α-hydroxyandrost-4-ene-17-carbonitrile 在 N-甲基吗啉 、 盐酸 、 potassium fluoride 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 65.17h， 生成 spiro-3'-pentyl-2',3,4',11-tetraone
  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
• 作为产物：
  描述：

  肾上腺甾酮 生成 3,11-dioxo-17α-hydroxyandrost-4-ene-17-carbonitrile
  参考文献：
  名称：

  TEICHMULLER, GERHARD;SCHMIDT, FRANK;GRAUPNER, ELKE;KRAHMER, SIGRID;RABE, +

  摘要：

  DOI：