(Z)-4-methyl-N,5-diphenylpent-4-enamide | 1282061-27-1

• 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: (Z)-4-methyl-N,5-diphenylpent-4-enamide
• CAS: 1282061-27-1
• 化学式: C₁₈H₁₉NO
• 分子量: 265.355
• InChiKey: CTZRJPRLCGTNBW-PFONDFGASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (Z)-4-methyl-N,5-diphenylpent-4-enamide 在 烟酸乙酯 、 氧气 、 palladium diacetate 、 sodium carbonate 作用下， 以 1,4-二氧六环 为溶剂， 70.0 ℃ 、101.33 kPa 条件下， 反应 72.0h， 以56%的产率得到(3aR,4R)-3a-methyl-4-phenyl-3,4-dihydro-2H-pyrrolo[1,2-a]indol-1-one
  参考文献：
  名称：

  Pd(II)-Catalyzed Intramolecular Amidoarylation of Alkenes with Molecular Oxygen as Sole Oxidant

  摘要：

  Stereoselective palladium-catalyzed synthesis of structurally versatile indoline derivatives, using molecular oxygen as the sole oxidant, is described. New C-N and C-C bonds form across an alkene in an intramolecular manner. The C-N bond-forming step proceeds via a syn-amidopalladation pathway. The moderate kinetic isotope effects (intramolecular KIE = 3.56) suggest that electrophilic aromatic substitution occurs in the arylation step.

  DOI：

  10.1021/ol2006083
• 作为产物：
  描述：

  (Z)-4-methyl-5-phenylpent-4-enoic acid 在 吡啶 、 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 (Z)-4-methyl-N,5-diphenylpent-4-enamide
  参考文献：
  名称：

  Pd(II)-Catalyzed Intramolecular Amidoarylation of Alkenes with Molecular Oxygen as Sole Oxidant

  摘要：

  Stereoselective palladium-catalyzed synthesis of structurally versatile indoline derivatives, using molecular oxygen as the sole oxidant, is described. New C-N and C-C bonds form across an alkene in an intramolecular manner. The C-N bond-forming step proceeds via a syn-amidopalladation pathway. The moderate kinetic isotope effects (intramolecular KIE = 3.56) suggest that electrophilic aromatic substitution occurs in the arylation step.

  DOI：

  10.1021/ol2006083

文献信息

• Pd(II)-Catalyzed Intramolecular Amidoarylation of Alkenes with Molecular Oxygen as Sole Oxidant
  作者：Kai-Tai Yip、Dan Yang

  DOI：10.1021/ol2006083

  日期：2011.4.15

  Stereoselective palladium-catalyzed synthesis of structurally versatile indoline derivatives, using molecular oxygen as the sole oxidant, is described. New C-N and C-C bonds form across an alkene in an intramolecular manner. The C-N bond-forming step proceeds via a syn-amidopalladation pathway. The moderate kinetic isotope effects (intramolecular KIE = 3.56) suggest that electrophilic aromatic substitution occurs in the arylation step.