ethyl [2,3-bis(methoxycarbonyl)propyl](vinyl)phosphinate | 1032101-85-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl [2,3-bis(methoxycarbonyl)propyl](vinyl)phosphinate
• 英文别名: Ethyl [2,3-bis(methoxycarbonyl)propyl](vinyl)-phosphinate；dimethyl 2-[[ethenyl(ethoxy)phosphoryl]methyl]butanedioate
• CAS: 1032101-85-1
• 化学式: C₁₁H₁₉O₆P
• 分子量: 278.242
• InChiKey: UVAMZDNKMZCAGW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  18
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl [2,3-bis(methoxycarbonyl)propyl](vinyl)phosphinate 在 盐酸 、 四丁基溴化铵 、 potassium carbonate 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 [2,3-bis(hydroxycarbonyl)propyl][3-amino-3-(hydroxycarbonyl)propyl]phosphinic acid
  参考文献：
  名称：

  Synthesis of phosphinic acids on the basis of hypophosphites: VI. General methods for synthesis of pseudo-γ-glutamylpeptides

  摘要：

  A general method for synthesis of 2-substituted pseudo-gamma-glutamylpeptides, namely, [2-(hydroxy-carbonyl)ethyl][3-amino-3-(hydroxycarbonyl)propyl]phosphinic acids I which are phosphinic acid analogs of,gamma-glutamylpeptides. Bis(trimethylsilyl) hypophosphite (IV) formed from ammonium hypophosphite (II) in situ was added to the respective ck-substituted acrylate to form bis(trimethylsilyl) [2-R-2-(alkoxycarbonyl)ethyl]phosphonites V. Treatment of compounds V in situ with excess dibromoethane followed by alcoholysis gave [2-R-2-( alkoxycarbon),I)ethyl](2-bromoethyl)phosphonic acids VI which without isolation were treated with excess triethyl orthoformate. The sirnultanious esterification and dehydrobrommation led to [2-R-2-( alkoxy-carbonyl)ethyl 1(vinyl)phosphinates III which were isolated and characterized. The Michael addition of diethyl acetamidomalonate to vinylphosphinates III followed by acid hydrolysis of phosphinates VII without their isolation resulted in formation of target [2-R-2-(hydi-oxycai-bonyl)ethyl][')-amino-3-(hydroxycarbonyl)]proyl]phosphinic acids-pseudo-gamma-glutamylpeptides I.

  DOI：

  10.1134/s1070363207050076
• 作为产物：
  描述：

  、 原甲酸三乙酯 生成 ethyl [2,3-bis(methoxycarbonyl)propyl](vinyl)phosphinate
  参考文献：
  名称：

  Synthesis of phosphinic acids on the basis of hypophosphites: VI. General methods for synthesis of pseudo-γ-glutamylpeptides

  摘要：

  A general method for synthesis of 2-substituted pseudo-gamma-glutamylpeptides, namely, [2-(hydroxy-carbonyl)ethyl][3-amino-3-(hydroxycarbonyl)propyl]phosphinic acids I which are phosphinic acid analogs of,gamma-glutamylpeptides. Bis(trimethylsilyl) hypophosphite (IV) formed from ammonium hypophosphite (II) in situ was added to the respective ck-substituted acrylate to form bis(trimethylsilyl) [2-R-2-(alkoxycarbonyl)ethyl]phosphonites V. Treatment of compounds V in situ with excess dibromoethane followed by alcoholysis gave [2-R-2-( alkoxycarbon),I)ethyl](2-bromoethyl)phosphonic acids VI which without isolation were treated with excess triethyl orthoformate. The sirnultanious esterification and dehydrobrommation led to [2-R-2-( alkoxy-carbonyl)ethyl 1(vinyl)phosphinates III which were isolated and characterized. The Michael addition of diethyl acetamidomalonate to vinylphosphinates III followed by acid hydrolysis of phosphinates VII without their isolation resulted in formation of target [2-R-2-(hydi-oxycai-bonyl)ethyl][')-amino-3-(hydroxycarbonyl)]proyl]phosphinic acids-pseudo-gamma-glutamylpeptides I.

  DOI：

  10.1134/s1070363207050076