20ξ-(Diethylphosphono)-20ξ-isocyano-3-methoxypregna-3,5-diene | 139527-71-2

• 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: 20ξ-(Diethylphosphono)-20ξ-isocyano-3-methoxypregna-3,5-diene
• CAS: 139527-71-2
• 化学式: C₂₇H₄₂NO₄P
• 分子量: 475.609
• InChiKey: KCVWQINQKGKYCM-NQPCHBBOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.14
• 重原子数：
  33.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  57.12
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  20ξ-(Diethylphosphono)-20ξ-isocyano-3-methoxypregna-3,5-diene 在 高氯酸 作用下， 以 1,4-二氧六环 为溶剂， 生成 黄体酮 、 黄体酮EP杂质M
  参考文献：
  名称：

  Chemistry of N,P-acetals: application to the synthesis of 20-ketosteroids

  摘要：

  A series of new derivatives of alpha-(isocyanomethyl)phosphonates (6a,b,c and 9) is described, which are formed by methylation of (E)-17-[(diethylphosphono)isocyanomethylene] steroids 5a,b,c and 17-beta-[(diethylphosphono)isocyanomethyl] steroid 8. It proved possible to hydrolyze these compounds under relatively mild conditions to 20-ketosteroids 7a,b,c and 10, showing for the first time that geminal N- and P-substituted carbon compounds do react as N,P-acetals.

  DOI：

  10.1021/jo00034a012
• 作为产物：
  描述：

  3-甲氧基雄甾-3,5-二烯-17-酮 在 sodium tetrahydroborate 、 potassium tert-butylate 、 二异丙胺 、 三氯氧磷 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 5.58h， 生成 20ξ-(Diethylphosphono)-20ξ-isocyano-3-methoxypregna-3,5-diene
  参考文献：
  名称：

  Chemistry of N,P-acetals: application to the synthesis of 20-ketosteroids

  摘要：

  A series of new derivatives of alpha-(isocyanomethyl)phosphonates (6a,b,c and 9) is described, which are formed by methylation of (E)-17-[(diethylphosphono)isocyanomethylene] steroids 5a,b,c and 17-beta-[(diethylphosphono)isocyanomethyl] steroid 8. It proved possible to hydrolyze these compounds under relatively mild conditions to 20-ketosteroids 7a,b,c and 10, showing for the first time that geminal N- and P-substituted carbon compounds do react as N,P-acetals.

  DOI：

  10.1021/jo00034a012