Ethyl 3-amino-4-oxo-2-pentenoate | 115975-43-4

• 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 3-amino-4-oxo-2-pentenoate
• 英文别名: ethyl (Z)-3-amino-4-oxopent-2-enoate
• CAS: 115975-43-4
• 化学式: C₇H₁₁NO₃
• 分子量: 157.169
• InChiKey: QJBKPPLTHDHEEG-XQRVVYSFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 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

• 作为产物：
  描述：

  Ethyl 3-azido-4-oxopentanoate 在 乙醛 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 以34%的产率得到Ethyl 3-amino-4-oxo-2-pentenoate
  参考文献：
  名称：

  Base-Promoted Reactions of .alpha.-Azido Ketones with Aldehydes and Ketones: A Novel Entry to .alpha.-Azido-.beta.-hydroxy Ketones and 2,5-Dihydro-5-hydroxyoxazoles

  摘要：

  The base-promoted reaction of alpha-azido ketones with aldehydes and ketones provides a new and simple route to either alpha-azido-beta-hydroxy ketones, which are valuable 1,2,3-trifunctionalized synthons, or 2,5-dihydro-5-hydroxyoxazoles, which are a little known type of oxazoline. These two products are formed by the electrophilic trapping of two different anions that are produced sequentially during the reaction, The alpha-azido-beta-hydroxy ketones are formed by an aldol reaction between an enolate of the alpha-azidoketone and an aldehyde. The 2,5-dihydro-5-hydroxyoxazoles are formed by electrophilic trapping of an imino anion which is produced by nitrogen loss from the cx-azido ketone enolate.

  DOI：

  10.1021/jo00113a015

文献信息

• Formation of α-enaminoketones from α-azidoketones: An elimination of molecular nitrogen from α-azidoketones
  作者：Karey Van Sant、Michael S. South

  DOI：10.1016/s0040-4039(00)96852-7

  日期：1987.1