(8R,9S,10R,11S,13S,14S)-13-Methyl-3,17-dioxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-11-carbonitrile | 478798-45-7

• 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: (8R,9S,10R,11S,13S,14S)-13-Methyl-3,17-dioxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-11-carbonitrile
• 英文别名: (8R,9S,10R,11S,13S,14S)-13-methyl-3,17-dioxo-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthrene-11-carbonitrile
• CAS: 478798-45-7
• 化学式: C₁₉H₂₃NO₂
• 分子量: 297.397
• InChiKey: LXVRZUHTKQDTHN-FPCVLZJASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  57.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (8R,9S,10R,11S,13S,14S)-13-Methyl-3,17-dioxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-11-carbonitrile 在 lithium bromide 、 copper(ll) bromide 作用下， 以 乙腈 为溶剂， 生成 (2S,8R,9S,10R,11S,13S,14S)-2-Bromo-13-methyl-3,17-dioxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-11-carbonitrile
  参考文献：
  名称：

  Synthesis of nitrile derivatives of estrogens

  摘要：

  The first time synthesis of 7alpha- and 11beta-nitrile estradiol is described. Reaction of 7alpha-cyano- 19-nortestosterone with copper(II) bromide in acetonitrile at room temperature results in aromatization of the A-ring. Treatment of 11beta-cyano-19-nortestosterone-17-one under similar condition does not induce A-ring aromatization but rather results in bromination at the 2beta-position. However A-ring aromatized products are obtained when the latter compound is treated with Ac2O-Py-AcOCI, NBS and HCl. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00634-0
• 作为产物：
  描述：

  对甲基苯磺酰甲基异腈 、 estr-5-ene-3,11,17-trione 3,17-bis(cyclic 1,2-ethanediyl acetal) 以 乙二醇二甲醚 为溶剂， 生成 (8R,9S,10R,11S,13S,14S)-13-Methyl-3,17-dioxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-11-carbonitrile 、 (8R,9S,10R,11R,13S,14S)-13-Methyl-3,17-dioxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-11-carbonitrile
  参考文献：
  名称：

  Synthesis of nitrile derivatives of estrogens

  摘要：

  The first time synthesis of 7alpha- and 11beta-nitrile estradiol is described. Reaction of 7alpha-cyano- 19-nortestosterone with copper(II) bromide in acetonitrile at room temperature results in aromatization of the A-ring. Treatment of 11beta-cyano-19-nortestosterone-17-one under similar condition does not induce A-ring aromatization but rather results in bromination at the 2beta-position. However A-ring aromatized products are obtained when the latter compound is treated with Ac2O-Py-AcOCI, NBS and HCl. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00634-0