4-(3-Methoxyphenyl)but-3-ynyl cyanoformate | 1280640-17-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-(3-Methoxyphenyl)but-3-ynyl cyanoformate
• 英文别名: 4-(3-methoxyphenyl)but-3-ynyl cyanoformate
• CAS: 1280640-17-6
• 化学式: C₁₃H₁₁NO₃
• 分子量: 229.235
• InChiKey: ZPQBDMVXVDSFAF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  59.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(3-Methoxyphenyl)but-3-ynyl cyanoformate 在 四(三苯基膦)钯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.08h， 以83%的产率得到C₁₃H₁₁NO₃
  参考文献：
  名称：

  Palladium-Catalyzed C−CN Activation for Intramolecular Cyanoesterification of Alkynes

  摘要：

  Conditions for the C-CN activation and intramolecular cyanoesterification of alkynes to provide butenolides in good to excellent yields are presented. Pd catalysts, high temperatures/short reaction times (microwave irradiation), and Lewis basic solvents minimized competitive decarbonylation. Less sterically encumbered, electron-rich alkynes underwent cyanoesterification with greater ease compared to sterically encumbered, electron-deficient alkynes. The results led to the hypothesis that migratory insertion of the alkyne, rather than C-CN activation, might be the product-determining step.

  DOI：

  10.1021/ol200274h
• 作为产物：
  描述：

  羰基二氰化物 、 4-(3-methoxyphenyl)but-3-yn-1-ol 以 乙醚 为溶剂， 反应 12.0h， 以72%的产率得到4-(3-Methoxyphenyl)but-3-ynyl cyanoformate
  参考文献：
  名称：

  Palladium-Catalyzed C−CN Activation for Intramolecular Cyanoesterification of Alkynes

  摘要：

  Conditions for the C-CN activation and intramolecular cyanoesterification of alkynes to provide butenolides in good to excellent yields are presented. Pd catalysts, high temperatures/short reaction times (microwave irradiation), and Lewis basic solvents minimized competitive decarbonylation. Less sterically encumbered, electron-rich alkynes underwent cyanoesterification with greater ease compared to sterically encumbered, electron-deficient alkynes. The results led to the hypothesis that migratory insertion of the alkyne, rather than C-CN activation, might be the product-determining step.

  DOI：

  10.1021/ol200274h