Acetic acid 4-chloro-1,1-bis-(diethoxy-phosphoryl)-butyl ester | 890847-95-7

• 英文名称: Acetic acid 4-chloro-1,1-bis-(diethoxy-phosphoryl)-butyl ester
• 英文别名: [4-Chloro-1,1-bis(diethoxyphosphoryl)butyl] acetate
• CAS: 890847-95-7
• 化学式: C₁₄H₂₉ClO₈P₂
• 分子量: 422.78
• InChiKey: ZJEHEBVTJWUONG-UHFFFAOYSA-N

物化性质

• 沸点：
  502.4±50.0 °C(Predicted)
• 密度：
  1.213±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  25
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  97.4
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  Acetic acid 4-chloro-1,1-bis-(diethoxy-phosphoryl)-butyl ester 在 palladium on activated charcoal sodium azide 、 氢气 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 60.0 ℃ 、101.33 kPa 条件下， 反应 17.0h， 生成 [4-Acetylamino-1-(diethoxy-phosphoryl)-1-hydroxy-butyl]-phosphonic acid diethyl ester
  参考文献：
  名称：

  Synthesis and Study of Alendronate Derivatives as Potential Prodrugs of Alendronate Sodium for the Treatment of Low Bone Density and Osteoporosis

  摘要：

  Alendronate derivatives were evaluated as potential prodrugs for the osteoporosis drug alendronate sodium in an attempt to enhance the systemic exposure after oral administration. An investigation of the chemical behavior of alendronate derivatives led to development of practical synthetic strategies and prediction of each structural class's prodrug potential. Pharmacokinetic studies of N-myristoylalendronic acid revealed that 25% have been converted in vivo after iv administration in rat, providing an important proof-of-concept for this strategy.

  DOI：

  10.1021/jm060398v
• 作为产物：
  描述：

  4-Chloro-1,1-bis(diethoxyphosphoryl)butan-1-ol 、 乙酰氯 反应 36.0h， 生成 Acetic acid 4-chloro-1,1-bis-(diethoxy-phosphoryl)-butyl ester
  参考文献：
  名称：

  Synthesis and Study of Alendronate Derivatives as Potential Prodrugs of Alendronate Sodium for the Treatment of Low Bone Density and Osteoporosis

  摘要：

  Alendronate derivatives were evaluated as potential prodrugs for the osteoporosis drug alendronate sodium in an attempt to enhance the systemic exposure after oral administration. An investigation of the chemical behavior of alendronate derivatives led to development of practical synthetic strategies and prediction of each structural class's prodrug potential. Pharmacokinetic studies of N-myristoylalendronic acid revealed that 25% have been converted in vivo after iv administration in rat, providing an important proof-of-concept for this strategy.

  DOI：

  10.1021/jm060398v