Acetic acid (3S,8R,9S,10R,13S,14S)-17-cyano-3-hydroxy-10,13-dimethyl-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl ester | 17006-14-3

• 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: Acetic acid (3S,8R,9S,10R,13S,14S)-17-cyano-3-hydroxy-10,13-dimethyl-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl ester
• CAS: 17006-14-3
• 化学式: C₂₂H₃₁NO₃
• 分子量: 357.493
• InChiKey: FLRMWQWGPTUUFN-CUDKJUOTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.14
• 重原子数：
  26.0
• 可旋转键数：
  1.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  70.32
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (3S,8R,9S,10R,13S,14S)-17-cyano-3-hydroxy-10,13-dimethyl-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl ester 在 吡啶 、 sodium carbonate 、 lithium tri-t-butoxyaluminum hydride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成
  参考文献：
  名称：

  A new class of long-acting hormonal steroid preparation: synthesis of dimeric androgens coupled at C3-C3 and C-17-C3 and of an androgen-progestogen combination

  摘要：

  3beta-Hydroxy-4-androsten-17-one was prepared from 4-androsten-3,17-dione according to the method of Klimstra and Colton (1) and dimerized by means of esterification with succinic acid. The reduction with lithium-tri-t-butoxyaluminium hydride gave a testosterone derivative coupled between C3-C3 which showed after a single injection of 10 mg a protracted but relatively weak androgenic effect in castrated male rats. The direct esterification of testosterone hemisuccinate with 4-androsten-3beta, 17beta-diol gave the testosterone derivative coupled between C17-C3 which showed a more even and more protracted time response curve than testosterone enanthate. The testosterone-ethynodiol succinate also coupled between C17-C3, showed an androgenic depot-effect similar to that of the dimeric C17-C3 testosterone derivative.

  DOI：

  10.1016/0039-128x(76)90128-8
• 作为产物：
  描述：

  雄烯二酮 在 lithium tri-t-butoxyaluminum hydride 作用下， 以 四氢呋喃 为溶剂， 生成 Acetic acid (3S,8R,9S,10R,13S,14S)-17-cyano-3-hydroxy-10,13-dimethyl-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl ester
  参考文献：
  名称：

  The synthesis of 3β-hydroxyestr-4-en-17-one and 3β-hydroxiandrost-4-en-17-one

  摘要：

  DOI：

  10.1016/0039-128x(67)90119-5