(E)-17-<(Diethylphosphono)formamidomethylene>-3-methoxyandrosta-3,5-diene | 139563-86-3

• 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: (E)-17-<(Diethylphosphono)formamidomethylene>-3-methoxyandrosta-3,5-diene
• 英文别名: (E)-17-[(Diethylphosphono)formamidomethylene]-3-methoxyandrosta-3,5-diene；N-[(E)-diethoxyphosphoryl-[(8R,9S,10R,13S,14S)-3-methoxy-10,13-dimethyl-1,2,7,8,9,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-17-ylidene]methyl]formamide
• CAS: 139563-86-3
• 化学式: C₂₆H₄₀NO₅P
• 分子量: 477.581
• InChiKey: YNLOCCPGAYTCOZ-LNTLRLOASA-N

物化性质

• 沸点：
  644.4±55.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.31
• 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：
  0.73
• 拓扑面积：
  73.86
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (E)-17-<(Diethylphosphono)formamidomethylene>-3-methoxyandrosta-3,5-diene 在 sodium tetrahydroborate 、 高氯酸 、 potassium tert-butylate 、 二异丙胺 、 三氯氧磷 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醇 为溶剂， 反应 4.42h， 生成 黄体酮
  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：

  异腈甲基磷酸二乙酯 、 3-甲氧基雄甾-3,5-二烯-17-酮 在 potassium tert-butylate 作用下， 生成 (E/Z)-17-(isocyanomethylene)-3-methoxyandrosta-3,5-diene 、 (E)-17-<(Diethylphosphono)formamidomethylene>-3-methoxyandrosta-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