ethyl 5-(benzyloxyamino)-5-oxopentanoate | 960149-58-0

• 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 5-(benzyloxyamino)-5-oxopentanoate
• 英文别名: Ethyl 5-oxo-5-(phenylmethoxyamino)pentanoate；ethyl 5-oxo-5-(phenylmethoxyamino)pentanoate
• CAS: 960149-58-0
• 化学式: C₁₄H₁₉NO₄
• 分子量: 265.309
• InChiKey: QRKXEMXPEOGKFL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  19
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  O-苄基羟胺 、 乙基(1R,2R)-2-甲酰基环丙烷羧酸酯 在 triazolium salt 咪唑 、 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 15.0h， 以53%的产率得到ethyl 5-(benzyloxyamino)-5-oxopentanoate
  参考文献：
  名称：

  N-Heterocyclic Carbene-Catalyzed Redox Amidations of α-Functionalized Aldehydes with Amines

  摘要：

  A catalytic method for the direct synthesis of carboxylic acid amides from amines and alpha-functionalized aldehydes is possible through the synergistic role of a N-heterocyclic carbene catalyst and imidazole, affording amides via activated carboxylates catalytically generated via an internal redox reaction of the aldehyde substrates. The use of imidazole or other N-heterocycles as an additive is essential to overcoming imine formation and serves as a uniquely reactive substrate for the generation of an acyl imidazolium intermediate that is converted to the final amide product.

  DOI：

  10.1021/ja0768136

文献信息

• N-Heterocyclic Carbene-Catalyzed Redox Amidations of α-Functionalized Aldehydes with Amines
  作者：Jeffrey W. Bode、Stephanie S. Sohn

  DOI：10.1021/ja0768136

  日期：2007.11.1

  A catalytic method for the direct synthesis of carboxylic acid amides from amines and alpha-functionalized aldehydes is possible through the synergistic role of a N-heterocyclic carbene catalyst and imidazole, affording amides via activated carboxylates catalytically generated via an internal redox reaction of the aldehyde substrates. The use of imidazole or other N-heterocycles as an additive is essential to overcoming imine formation and serves as a uniquely reactive substrate for the generation of an acyl imidazolium intermediate that is converted to the final amide product.