[2-(hydroxycarbonyl)propyl][3-amino-3-(hydroxycarbonyl)propyl]phosphinic acid

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: [2-(hydroxycarbonyl)propyl][3-amino-3-(hydroxycarbonyl)propyl]phosphinic acid
• 英文别名: 2-Amino-4-[2-carboxypropyl(hydroxy)phosphoryl]butanoic acid
• 化学式: C₈H₁₆NO₆P
• 分子量: 253.192
• InChiKey: XJLAKNBTWHOYHE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.3
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  138
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  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-(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

文献信息

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

  DOI：10.1134/s1070363207050076

  日期：2007.5

  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.