N-benzyl-3-(4-ethanoylphenyl)propanamide | 960149-63-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-benzyl-3-(4-ethanoylphenyl)propanamide
• 英文别名: 3-(4-acetylphenyl)-N-benzylpropanamide
• CAS: 960149-63-7
• 化学式: C₁₈H₁₉NO₂
• 分子量: 281.354
• InChiKey: SBVPLUPVXJZOAI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (E)-3-(4-acetylphenyl)acrylaldehyde 、 苄胺 在 triazolium salt 咪唑 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 15.33h， 以56%的产率得到N-benzyl-3-(4-ethanoylphenyl)propanamide
  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.