[2-(Benzylamino)-1-(4-nitrophenyl)-2-oxoethyl] pent-4-enoate | 1040354-28-6

• 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: [2-(Benzylamino)-1-(4-nitrophenyl)-2-oxoethyl] pent-4-enoate
• CAS: 1040354-28-6
• 化学式: C₂₀H₂₀N₂O₅
• 分子量: 368.389
• InChiKey: JTXOOPGAUYRSHE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  101
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-戊烯酸 、 苄异腈 、 对硝基苯甲醛 以 甲醇 为溶剂， 反应 12.0h， 以83%的产率得到[2-(Benzylamino)-1-(4-nitrophenyl)-2-oxoethyl] pent-4-enoate
  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

• Catalysis of Ugi Four Component Coupling Reactions by Rare Earth Metal Triflates
  作者：Babajide O. Okandeji、Jonathan R. Gordon、Jason K. Sello

  DOI：10.1021/jo800745a

  日期：2008.7.1

  Substoichiometric quantities of scandium and ytterbium triflate increase the yield of Ugi four component coupling reactions of aromatic aldehydes 2- to 7-fold. These rare earth metal triflates enhance the reaction yields primarily via activation of the imine intermediate of this multicomponent reaction.