pregnenolone acetate 20-cyanohydrin | 22641-61-8

• 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: pregnenolone acetate 20-cyanohydrin
• 英文别名: markiertes 3β-Acetoxy-20-hydroxy-20-cyan-Δ⁵-pregnen；[(3S,8S,9S,10R,13S,14S,17S)-17-(1-cyano-1-hydroxyethyl)-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate
• CAS: 22641-61-8
• 化学式: C₂₄H₃₅NO₃
• 分子量: 385.547
• InChiKey: CGKWLCMNOXWDRB-FRBBPBPFSA-N

物化性质

• 熔点：
  154.5-156.5 °C
• 沸点：
  518.4±30.0 °C(Predicted)
• 密度：
  1.13±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：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  70.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  pregnenolone acetate 20-cyanohydrin 在 sodium tungstate 、 三氯化铝 吡啶 、 sodium chlorite 、 periodate reagent 、 双氧水 、 二异丁基氢化铝 、 三乙胺 、 三氯氧磷 作用下， 以 吡啶 、 氘代吡啶 为溶剂， 生成 16-妊娠双烯醇酮
  参考文献：
  名称：

  Synthesis of 16-dehydro-20-oxopregnanes from 17α,20-epoxy-23,24-dinorcholan-22-oic acids. Highly stereospecific oxirane → allyl alcohol isomerization of an epoxycarboxylic acid

  摘要：

  A microbial degradation product of natural sterols was converted into traditional precursor of steroid syntheses by a simple sequence. The title isomerization, the key step, was investigated to demonstrate a concerted mechanism, in which a cyclic transition state, involving the oxirane oxygen, the beta- and gamma-carbon, the gamma-proton to be removed and the catalyst coordinated by the carboxylate group, is postulated.

  DOI：

  10.1016/s0040-4039(00)78366-3
• 作为产物：
  描述：

  16-脱氢孕烯醇酮乙酸酯 在 palladium on activated charcoal 氢气 作用下， 生成 pregnenolone acetate 20-cyanohydrin
  参考文献：
  名称：

  Synthesis of 16-dehydro-20-oxopregnanes from 17α,20-epoxy-23,24-dinorcholan-22-oic acids. Highly stereospecific oxirane → allyl alcohol isomerization of an epoxycarboxylic acid

  摘要：

  A microbial degradation product of natural sterols was converted into traditional precursor of steroid syntheses by a simple sequence. The title isomerization, the key step, was investigated to demonstrate a concerted mechanism, in which a cyclic transition state, involving the oxirane oxygen, the beta- and gamma-carbon, the gamma-proton to be removed and the catalyst coordinated by the carboxylate group, is postulated.

  DOI：

  10.1016/s0040-4039(00)78366-3

文献信息

• Benzoyl trifluoromethanesulfonate. A mild reagent for the benzoylation of sterically hindered hydroxyls
  作者：Lindsey Brown、Masato Koreeda

  DOI：10.1021/jo00195a001

  日期：1984.10
• Kalvoda,J. et al., Helvetica Chimica Acta, 1966, vol. 49, p. 424 - 436
  作者：Kalvoda,J. et al.

  DOI：——

  日期：——