Methyl 3-bromoandrosta-3,5-diene-17β-carboxylate | 119169-85-6

• 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: Methyl 3-bromoandrosta-3,5-diene-17β-carboxylate
• 英文别名: methyl (8S,9S,10R,13S,14S,17S)-3-bromo-10,13-dimethyl-2,7,8,9,11,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthrene-17-carboxylate
• CAS: 119169-85-6
• 化学式: C₂₁H₂₉BrO₂
• 分子量: 393.364
• InChiKey: FQMFMBKUJMQDRW-YFWFAHHUSA-N

物化性质

• 沸点：
  457.1±45.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Methyl 3-bromoandrosta-3,5-diene-17β-carboxylate 在 氢氧化钾 、 草酰氯 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 28.5h， 生成 爱普列特
  参考文献：
  名称：

  Improved Syntheses of Epristeride, a Potent Human 5.alpha.-Reductase Inhibitor

  摘要：

  Two improved syntheses of a potent human 5 alpha-reductase inhibitor, epristeride, SK&F 105657, are described. The first synthesis starts from methyl 3-oxoandrost-4-ene-17 beta-carboxylate (1), which is converted to epristeride (5) in four synthetic steps in 44% overall yield. The second synthesis starts from commercially available 3-oxoandrost-4-en-17 beta-carboxylic acid (7), which is converted to epristeride (5) in two synthetic steps in 63% overall yield. Both syntheses are suitable for large scale production and have been employed to produce kilograms supplies of epristeride in high purity.

  DOI：

  10.1021/jo00099a031
• 作为产物：
  描述：

  雄甾-3-酮-4-烯-17bata-羧酸甲酯 在 三溴化磷 作用下， 以 溶剂黄146 为溶剂， 反应 21.0h， 以85%的产率得到Methyl 3-bromoandrosta-3,5-diene-17β-carboxylate
  参考文献：
  名称：

  Improved Syntheses of Epristeride, a Potent Human 5.alpha.-Reductase Inhibitor

  摘要：

  Two improved syntheses of a potent human 5 alpha-reductase inhibitor, epristeride, SK&F 105657, are described. The first synthesis starts from methyl 3-oxoandrost-4-ene-17 beta-carboxylate (1), which is converted to epristeride (5) in four synthetic steps in 44% overall yield. The second synthesis starts from commercially available 3-oxoandrost-4-en-17 beta-carboxylic acid (7), which is converted to epristeride (5) in two synthetic steps in 63% overall yield. Both syntheses are suitable for large scale production and have been employed to produce kilograms supplies of epristeride in high purity.

  DOI：

  10.1021/jo00099a031