N-ethylhydroxyglycine | 141555-53-5

• 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: N-ethylhydroxyglycine
• 英文别名: 2-(Ethylamino)-2-hydroxyacetic acid
• CAS: 141555-53-5
• 化学式: C₄H₉NO₃
• 分子量: 119.12
• InChiKey: NUHKBHGDYCAQTL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.1
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  69.6
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  乙胺 、 乙醛酸 以 水 为溶剂， 反应 48.0h， 以33.6%的产率得到N-ethylhydroxyglycine
  参考文献：
  名称：

  The reaction of glyoxylic acid with ammonia revisited

  摘要：

  Upon addition of ammonia or an alkylamine to glyoxylic acid an ammonium derivative of glyoxylic acid precipitates quantitatively. With the use of solid-state C-13 and N-15 NMR spectroscopy, it is shown that adducts of glyoxylic acid and ammonia or the alkylamine are obtained. These compounds are not stable in aqueous solution. The compositions of the aqueous solutions have been investigated by H-1, C-13, N-15, and O-17 NMR. Under basic conditions hexahydro-s-triazine-2,4,6-tricarboxylate is the predominant species in a solution of the adduct of ammonia and glyoxylic acid, whereas upon acidification (pH < 6) glyoxylate is the only organic species. In a basic solution of the adduct of ethylamine and glyoxylic acid N-ethylirainoacetate is the only species. The N-methyl adduct shows an intermediate behavior: both the hexahydrotriazine and the imine are observed. Under acidic conditions deamination to glyoxylate always occurs. Intermediates in the reaction of glyoxylic acid and ammonia could be detected with H-1 NMR, when the reaction was performed with an excess of ammonia. The mechanism of these reactions is discussed.

  DOI：

  10.1021/jo00040a035

文献信息

• The reaction of glyoxylic acid with ammonia revisited
  作者：Anthonius J. Hoefnagel、Herman Van Bekkum、Joop A. Peters

  DOI：10.1021/jo00040a035

  日期：1992.7

  Upon addition of ammonia or an alkylamine to glyoxylic acid an ammonium derivative of glyoxylic acid precipitates quantitatively. With the use of solid-state C-13 and N-15 NMR spectroscopy, it is shown that adducts of glyoxylic acid and ammonia or the alkylamine are obtained. These compounds are not stable in aqueous solution. The compositions of the aqueous solutions have been investigated by H-1, C-13, N-15, and O-17 NMR. Under basic conditions hexahydro-s-triazine-2,4,6-tricarboxylate is the predominant species in a solution of the adduct of ammonia and glyoxylic acid, whereas upon acidification (pH < 6) glyoxylate is the only organic species. In a basic solution of the adduct of ethylamine and glyoxylic acid N-ethylirainoacetate is the only species. The N-methyl adduct shows an intermediate behavior: both the hexahydrotriazine and the imine are observed. Under acidic conditions deamination to glyoxylate always occurs. Intermediates in the reaction of glyoxylic acid and ammonia could be detected with H-1 NMR, when the reaction was performed with an excess of ammonia. The mechanism of these reactions is discussed.