ethyl 7-((2-(hydroxymethyl)phenyl)amino)hept-2-enoate | 1429207-05-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ethyl 7-((2-(hydroxymethyl)phenyl)amino)hept-2-enoate
• 英文别名: ethyl (E)-7-[2-(hydroxymethyl)anilino]hept-2-enoate
• CAS: 1429207-05-5
• 化学式: C₁₆H₂₃NO₃
• 分子量: 277.364
• InChiKey: DZGGUTSBSPXODY-VZUCSPMQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  20
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  邻氨基苯甲醇 、 ethyl 7-oxohept-2-enoate 在 sodium cyanoborohydride 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 ethyl 7-((2-(hydroxymethyl)phenyl)amino)hept-2-enoate 、 ethyl 7-((2-(hydroxymethyl)phenyl)amino)hept-2-enoate
  参考文献：
  名称：

  Metal-Free α-Amination of Secondary Amines: Computational and Experimental Evidence for Azaquinone Methide and Azomethine Ylide Intermediates

  摘要：

  We have performed a combined computational and experimental study to elucidate the mechanism of a metal-free alpha-amination of secondary amines. Calculations predicted azaquinone methides and azomethine ylides as the reactive intermediates and showed that iminium ions are unlikely to participate in these transformations. These results were confirmed by experimental deuterium-labeling studies and the successful trapping of the postulated azomethine ylide and azaquinone methide intermediates. In addition, computed barrier heights for the rate-limiting step correlate qualitatively with experimental findings.

  DOI：

  10.1021/jo400483h

文献信息

• Metal-Free α-Amination of Secondary Amines: Computational and Experimental Evidence for Azaquinone Methide and Azomethine Ylide Intermediates
  作者：Arne Dieckmann、Matthew T. Richers、Alena Yu. Platonova、Chen Zhang、Daniel Seidel、K. N. Houk

  DOI：10.1021/jo400483h

  日期：2013.4.19

  We have performed a combined computational and experimental study to elucidate the mechanism of a metal-free alpha-amination of secondary amines. Calculations predicted azaquinone methides and azomethine ylides as the reactive intermediates and showed that iminium ions are unlikely to participate in these transformations. These results were confirmed by experimental deuterium-labeling studies and the successful trapping of the postulated azomethine ylide and azaquinone methide intermediates. In addition, computed barrier heights for the rate-limiting step correlate qualitatively with experimental findings.