3-Phenyl-propynoic acid benzyl-(benzylcarbamoyl-furan-2-yl-methyl)-amide | 440121-42-6

• 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: 3-Phenyl-propynoic acid benzyl-(benzylcarbamoyl-furan-2-yl-methyl)-amide
• 英文别名: N-benzyl-N-[2-(benzylamino)-1-(furan-2-yl)-2-oxoethyl]-3-phenylprop-2-ynamide
• CAS: 440121-42-6
• 化学式: C₂₉H₂₄N₂O₃
• 分子量: 448.521
• InChiKey: NYCJVFNNCVUNAB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  34
• 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：
  62.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-Phenyl-propynoic acid benzyl-(benzylcarbamoyl-furan-2-yl-methyl)-amide 在 ytterbium(III) triflate 作用下， 以 1,4-二氧六环 为溶剂， 以91%的产率得到N,2-dibenzyl-5-hydroxy-3-oxo-4-phenylisoindoline-1-carboxamide
  参考文献：
  名称：

  Studies on the sequential multi-component coupling/Diels–Alder cycloaddition reaction

  摘要：

  The synthesis of highly functionalized oxabicyclo[2.2.1]heptadiene derivatives through the sequential Use of all Ugi or Passerini multi-component coupling reaction followed by an intramolecular acetylene/furan Diels-Alder reaction was investigated. The nature of the heteroatom in the tether was determined to play a critical role. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)02299-7
• 作为产物：
  描述：

  糠醛 、 苄异腈 、 苯丙炔酸 以 甲醇 为溶剂， 反应 12.0h， 以4%的产率得到Phenyl-propynoic acid benzylcarbamoyl-furan-2-yl-methyl ester
  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