hydroxysarcosine | 141555-52-4

• 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: hydroxysarcosine
• 英文别名: Hydroxy(methylamino)acetic acid；2-hydroxy-2-(methylamino)acetic acid
• CAS: 141555-52-4
• 化学式: C₃H₇NO₃
• 分子量: 105.093
• InChiKey: UFEVCHNDUJQYRK-UHFFFAOYSA-N

物化性质

• 沸点：
  280.3±30.0 °C(Predicted)
• 密度：
  1.323±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -3.4
• 重原子数：
  7
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  69.6
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  hydroxysarcosine 、 2-甲氨基-5-氯二苯甲酮 以 乙醇 、 水 为溶剂， 反应 24.0h， 以71%的产率得到6-chloro-1,2-dihydro-1,3-dimethyl-4-phenylquinazoline-2-carboxylic acid
  参考文献：
  名称：

  羟基甘氨酸的反应。4-苯基喹唑啉衍生物的新合成路线

  摘要：

  羟基甘氨酸与2-氨基二苯甲酮的反应以高收率和在温和的条件下得到1,2-二氢-4-苯基-喹唑啉-2-羧酸。它们可以分别通过重排和通过空气氧化而平滑地转化为相应的3，4-二氢异构体和喹唑啉衍生物。6-氯-1,2-二氢-1-甲基-4-苯基喹唑啉-2-羧酸的X射线晶体结构显示C（2）处的羧酸根和N（1）处的甲基位于轴向位置。

  DOI：

  10.1016/s0040-4020(01)80432-4
• 作为产物：
  描述：

  甲胺 、 乙醛酸 以 水 为溶剂， 反应 48.0h， 以56%的产率得到hydroxysarcosine
  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.
• Reactions of hydroxyglycines. New synthetic routes to 4-phenylquinazoline derivatives
  作者：Anthonius J. Hoefnagel、Henk van Koningsveld、Frank van Meurs、Joop A. Peters、Anton Sinnema、Herman van Bekkum

  DOI：10.1016/s0040-4020(01)80432-4

  日期：1993.7

  Reaction of hydroxyglycine with 2-aminobenzophenones gives 1,2-dihydro-4-phenyl-quinazoline-2-carboxylic acids in high yields and under mild conditions. These can be smoothly converted into the corresponding 3,4-dihydro isomers and into quinazoline derivatives via rearrangement and oxidation by air, respectively. The X-ray crystallographic structure of 6-chloro-1,2-dihydro-1-methyl-4-phenylquinazoline-2-carboxylic

  羟基甘氨酸与2-氨基二苯甲酮的反应以高收率和在温和的条件下得到1,2-二氢-4-苯基-喹唑啉-2-羧酸。它们可以分别通过重排和通过空气氧化而平滑地转化为相应的3，4-二氢异构体和喹唑啉衍生物。6-氯-1,2-二氢-1-甲基-4-苯基喹唑啉-2-羧酸的X射线晶体结构显示C（2）处的羧酸根和N（1）处的甲基位于轴向位置。