N-(Ethoxycarbonyl)-2-cyano-4-phenyl-1-azabutadiene | 147688-82-2

• 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: N-(Ethoxycarbonyl)-2-cyano-4-phenyl-1-azabutadiene
• 英文别名: ethyl (NZ)-N-[(E)-1-cyano-3-phenylprop-2-enylidene]carbamate
• CAS: 147688-82-2
• 化学式: C₁₃H₁₂N₂O₂
• 分子量: 228.25
• InChiKey: OKWACBKMAWKONL-YHAURASGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  62.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(Ethoxycarbonyl)-2-cyano-4-phenyl-1-azabutadiene 、 丙烯酸甲酯（MA） 反应 25.0h， 生成 Methyl N-(ethoxycarbonyl)-1,2,3,4-tetrahydro(3S^*,4R^*)-4-phenyl-6-cyanonicotinate 、 Methyl N-(ethoxycarbonyl)-1,2,3,4-tetrahydro(3S^*,4S^*)-4-phenyl-6-cyanonicotinate
  参考文献：
  名称：

  Diels-Alder reaction of 2-cyano-1-azadienes. The effect of nitrogen substituents

  摘要：

  The Diels-Alder reactions of 2-cyano-1-aza dienes with three nitrogen substituents possessing different electronic requirements (phenyl, CO2C2H5, and OCH3) were studied with three dienophiles with different electronic requirements (styrene, methyl acrylate, and ethyl vinyl ether). The N-phenyl substituent aza diene was equally reactive with all three dienophiles. The N-CO2C2H5-substituted aza diene behaved as an electrophilic diene being more reactive with the electron-rich ethyl vinyl ether than styrene or methyl acrylate. The N-CO2C2H5-substituted aza diene is more reactive with all three dienophiles, including methyl acrylate, than the N-phenyl substituent azadiene. The N-OCH3-substituted aza diene was unreactive with all three dienophiles under the conditions investigated.

  DOI：

  10.1021/jo00060a023
• 作为产物：
  描述：

  N-(ethoxycarbonyl)triphenylphosphinimine 、 (E)-cinnamoyl cyanide 以 苯 为溶剂， 反应 22.0h， 以25%的产率得到N-(Ethoxycarbonyl)-2-cyano-4-phenyl-1-azabutadiene
  参考文献：
  名称：

  Diels-Alder reaction of 2-cyano-1-azadienes. The effect of nitrogen substituents

  摘要：

  The Diels-Alder reactions of 2-cyano-1-aza dienes with three nitrogen substituents possessing different electronic requirements (phenyl, CO2C2H5, and OCH3) were studied with three dienophiles with different electronic requirements (styrene, methyl acrylate, and ethyl vinyl ether). The N-phenyl substituent aza diene was equally reactive with all three dienophiles. The N-CO2C2H5-substituted aza diene behaved as an electrophilic diene being more reactive with the electron-rich ethyl vinyl ether than styrene or methyl acrylate. The N-CO2C2H5-substituted aza diene is more reactive with all three dienophiles, including methyl acrylate, than the N-phenyl substituent azadiene. The N-OCH3-substituted aza diene was unreactive with all three dienophiles under the conditions investigated.

  DOI：

  10.1021/jo00060a023

文献信息

• Diels-Alder reaction of 2-cyano-1-azadienes. The effect of nitrogen substituents
  作者：Celine Trione、Leticia M. Toledo、Scott D. Kuduk、Frank W. Fowler、David S. Grierson

  DOI：10.1021/jo00060a023

  日期：1993.4

  The Diels-Alder reactions of 2-cyano-1-aza dienes with three nitrogen substituents possessing different electronic requirements (phenyl, CO2C2H5, and OCH3) were studied with three dienophiles with different electronic requirements (styrene, methyl acrylate, and ethyl vinyl ether). The N-phenyl substituent aza diene was equally reactive with all three dienophiles. The N-CO2C2H5-substituted aza diene behaved as an electrophilic diene being more reactive with the electron-rich ethyl vinyl ether than styrene or methyl acrylate. The N-CO2C2H5-substituted aza diene is more reactive with all three dienophiles, including methyl acrylate, than the N-phenyl substituent azadiene. The N-OCH3-substituted aza diene was unreactive with all three dienophiles under the conditions investigated.