(Z)-2-Amino-4-oxo-hex-2-enoic acid methyl ester | 142311-58-8

• 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: (Z)-2-Amino-4-oxo-hex-2-enoic acid methyl ester
• 英文别名: methyl (Z)-2-amino-4-oxohex-2-enoate
• CAS: 142311-58-8
• 化学式: C₇H₁₁NO₃
• 分子量: 157.169
• InChiKey: XBQVXDCZHXXRDP-XQRVVYSFSA-N

物化性质

• 沸点：
  278.7±35.0 °C(Predicted)
• 密度：
  1.108±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  69.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (Z)-2-Amino-4-oxo-hex-2-enoic acid methyl ester 在 甲醇 、 硫酸氢铵 、 potassium dihydrogenphosphate 、 baker's yeast 、 乙醇 、 葡萄糖 、 magnesium sulfate 作用下， 以 水 为溶剂， 反应 24.0h， 以71%的产率得到Methyl 2-hydroxy-4-oxohexanoate
  参考文献：
  名称：

  Regio - and enantioselective bioreduction of ethyl 2,4-dioxoalkanoates and γ-Keto-α-enamino esters with fermenting baker's yeast

  摘要：

  2,4-Dioxoalkanoates 1a-d and the parent compounds gamma-keto-alpha-enamino esters 2a-d are regioselectively reduced by baker's yeast to (R)-alpha-hydroxy-gamma-ketoesters 4a-d in moderate to good chemical yield and appreciable enantioselectivity. Pig liver esterase enantioselective hydrolysis of the acetyl derivatives 3a-d, easily obtained by treatment of racemic alpha-hydroxy-gamma-keto esters 4a-d, produced the optically active (S) 4a-d in good chemical (60-92%) and optical (53-92%) yield.

  DOI：

  10.1016/s0040-4039(00)78883-6
• 作为产物：
  描述：

  methyl 2,4-dioxohexanoate 在 ammonium acetate 作用下， 以 溶剂黄146 、 苯 为溶剂， 生成 (Z)-2-Amino-4-oxo-hex-2-enoic acid methyl ester
  参考文献：
  名称：

  Regio - and enantioselective bioreduction of ethyl 2,4-dioxoalkanoates and γ-Keto-α-enamino esters with fermenting baker's yeast

  摘要：

  2,4-Dioxoalkanoates 1a-d and the parent compounds gamma-keto-alpha-enamino esters 2a-d are regioselectively reduced by baker's yeast to (R)-alpha-hydroxy-gamma-ketoesters 4a-d in moderate to good chemical yield and appreciable enantioselectivity. Pig liver esterase enantioselective hydrolysis of the acetyl derivatives 3a-d, easily obtained by treatment of racemic alpha-hydroxy-gamma-keto esters 4a-d, produced the optically active (S) 4a-d in good chemical (60-92%) and optical (53-92%) yield.

  DOI：

  10.1016/s0040-4039(00)78883-6

文献信息

• Decatungstate-Catalyzed Photochemical Synthesis of Enaminones from Vinyl Azides and Aldehydes
  作者：Stanislav A. Paveliev、Oleg O. Segida、Olga M. Mulina、Igor B. Krylov、Alexander O. Terent’ev

  DOI：10.1021/acs.orglett.2c03364

  日期：2022.12.16

  Visible light-induced synthesis of enaminones from vinyl azides and aldehydes under decatungstate photocatalysis was developed. The reaction proceeds via acyl radical generation from aldehyde, followed by its addition to vinyl azide, nitrogen elimination, hydrogen atom abstraction by the intermediate iminyl radical, and tautomerization. Photochemical synthesis was efficiently conducted under both batch

  开发了在十钨酸盐光催化下从乙烯基叠氮化物和醛类的可见光诱导合成烯胺酮。该反应通过从醛产生酰基自由基，然后将其加成到乙烯基叠氮化物、氮消除、中间体亚胺基自由基夺取氢原子和互变异构来进行。光化学合成在分批和流动条件下均有效进行。该方法可应用于各种乙烯基叠氮化物和醛，并以 15-72% 的收率提供所需的产品。