5α-androstan-3β,17α-diyl diacetate | 909-07-9

• 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: 5α-androstan-3β,17α-diyl diacetate
• 英文别名: 3β,17α-Diacetoxy-5α-androstan；3β,17α-diacetoxy-5α-androstane；(10S)-3c.17t-Diacetoxy-10r.13c-dimethyl-(5tH.8cH.9tH.14tH)-hexadecahydro-1H-cyclopenta[a]phenanthren；5α-Androstandiyl-(3β.17α)-diacetat；[(3S,5S,8R,9S,10S,13S,14S,17R)-17-acetyloxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate
• CAS: 909-07-9
• 化学式: C₂₃H₃₆O₄
• 分子量: 376.536
• InChiKey: BQIBBYLXJDSLIR-CULVSFGYSA-N

物化性质

• 熔点：
  141-142 °C
• 沸点：
  440.150±18.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.103±0.10 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-乙酰基-5Α-雄烷二醇 在 吡啶 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 26.0h， 生成 5α-androstan-3β,17α-diyl diacetate
  参考文献：
  名称：

  Practical synthesis of androgen: the efficient transformation of 17-oxo group to 17α-hydroxy group

  摘要：

  The present report describes the improved transformation of the 17-oxo group in 3 beta-acetoxy-5 alpha-androstan-17-one to a 17 alpha-hydroxy group. A mixture of 17 alpha-acetoxy and 16-ene compounds, which are usually produced by the standard synthetic route, were treated with peracetic acid (epoxidation of the 16-ene compound) and then sodium hydroxide (reduction-hydrolysis) to give the desired 17 alpha-hydroxy compound in much better yield than that in previous reports. Recrystallization of the crude product with cyclohexane-methanol gave the pure compound in 54% yield (total yield from starting ketone). (Steroids 63:630-632). (C) 1998 by Elsevier Science Inc.

  DOI：

  10.1016/s0039-128x(98)00067-1

文献信息

• Francisco, Cosme G.; Freire, Raimundo; Hernandez, Rosendo, Journal of the Chemical Society. Perkin transactions I, 1983, p. 297 - 304
  作者：Francisco, Cosme G.、Freire, Raimundo、Hernandez, Rosendo、Melian, Daniel、Salazar, Jose A.、Suarez, Ernesto

  DOI：——

  日期：——
• Sexualhormone XV. Über cis-Testosteron und andere 17-cis-Oxyderivate des Androstans und Androstens
  作者：L. Ruzicka、H. Kägi

  DOI：10.1002/hlca.193601901115

  日期：——
• Practical synthesis of androgen: the efficient transformation of 17-oxo group to 17α-hydroxy group
  作者：Tetsuo Ohta、Huyue Zhang、Yoshitaka Torihara、Takemasa Hida、Isao Furukawa

  DOI：10.1016/s0039-128x(98)00067-1

  日期：1998.12

  The present report describes the improved transformation of the 17-oxo group in 3 beta-acetoxy-5 alpha-androstan-17-one to a 17 alpha-hydroxy group. A mixture of 17 alpha-acetoxy and 16-ene compounds, which are usually produced by the standard synthetic route, were treated with peracetic acid (epoxidation of the 16-ene compound) and then sodium hydroxide (reduction-hydrolysis) to give the desired 17 alpha-hydroxy compound in much better yield than that in previous reports. Recrystallization of the crude product with cyclohexane-methanol gave the pure compound in 54% yield (total yield from starting ketone). (Steroids 63:630-632). (C) 1998 by Elsevier Science Inc.