N-benzyl-N-[2-(benzylamino)-2-oxo-1-phenylethyl]-3-phenylprop-2-ynamide | 1159613-69-0

• 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: N-benzyl-N-[2-(benzylamino)-2-oxo-1-phenylethyl]-3-phenylprop-2-ynamide
• CAS: 1159613-69-0
• 化学式: C₃₁H₂₆N₂O₂
• 分子量: 458.56
• InChiKey: IOCUAKQJDWGJNS-UHFFFAOYSA-N

物化性质

• 密度：
  1.22±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  35
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  49.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  苄异腈 、 苯甲醛 、 苯丙炔酸 以 甲醇 为溶剂， 反应 12.0h， 以11%的产率得到[2-(Benzylamino)-2-oxo-1-phenylethyl] 3-phenylprop-2-ynoate
  参考文献：
  名称：

  Brønsted Acidity of Substrates Influences the Outcome of Passerini Three-Component Reactions

  摘要：

  Passerini three-component reactions of aldehydes, isocyanides, and strong carboxylic acids (i.e., pK(a) < 2) yield alpha-acyloxycarboxamides and/or alpha-acylaminocarbox amides, the characteristic products of Ugi four-component reactions. We propose that alpha-acylaminocarboxamide formation with these substrates is a consequence of in situ Bronsted acid-catalyzed reaction of the isocyanide and aldehyde to yield an imine that participates in an Ugi-type reaction. The apparent transfer of the isocyanide alpha-carbon to protic solvents as a formyl group during imine formation is indicative of new isocyanide reactivity.

  DOI：

  10.1021/jo900831n

文献信息

• Brønsted Acidity of Substrates Influences the Outcome of Passerini Three-Component Reactions
  作者：Babajide O. Okandeji、Jason K. Sello

  DOI：10.1021/jo900831n

  日期：2009.7.17

  Passerini three-component reactions of aldehydes, isocyanides, and strong carboxylic acids (i.e., pK(a) < 2) yield alpha-acyloxycarboxamides and/or alpha-acylaminocarbox amides, the characteristic products of Ugi four-component reactions. We propose that alpha-acylaminocarboxamide formation with these substrates is a consequence of in situ Bronsted acid-catalyzed reaction of the isocyanide and aldehyde to yield an imine that participates in an Ugi-type reaction. The apparent transfer of the isocyanide alpha-carbon to protic solvents as a formyl group during imine formation is indicative of new isocyanide reactivity.