(E)-3-{[1-Pyridin-3-yl-meth-(E)-ylidene]-amino}-acrylic acid ethyl ester | 244238-86-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (E)-3-{[1-Pyridin-3-yl-meth-(E)-ylidene]-amino}-acrylic acid ethyl ester
• CAS: 244238-86-6
• 化学式: C₁₁H₁₂N₂O₂
• 分子量: 204.228
• InChiKey: KVRLRJTYELNPQF-WWFUZLPXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.58
• 重原子数：
  15.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  51.55
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (E)-3-{[1-Pyridin-3-yl-meth-(E)-ylidene]-amino}-acrylic acid ethyl ester 在 对苯醌 作用下， 以 1,4-二氧六环 、 氯仿 为溶剂， 反应 48.0h， 生成 Ethyl 1-pyridin-3-yl-5,6,7,8-tetrahydroisoquinoline-4-carboxylate
  参考文献：
  名称：

  Reaction of N-Vinylic Phosphazenes Derived from β-Amino Acids with Aldehydes. Azadiene-Mediated Synthesis of Dihydropyridines, Pyridines, and Polycyclic Nitrogen Derivatives

  摘要：

  Enamino phosphonium salts 2 are obtained by 1,2-addition of hydrogen chloride to N-vinylic phosphazenes 1 derived from triphenylphosphine. Aza-Wittig reaction of phosphazenes 1 derived from triphenylphosphine and 6 derived from diphenylmethylphosphine with aldehydes 3 leads to the formation of 2-azadienes 7. Reaction of azadienes 7 with enamines affords dihydropyridines 9 and 11, pyridines 12, and bicyclic nitrogen heterocycles 15-18 in a regioselective fashion, while heterodiene 20 reacts in the same way with pyrrolidinocyclohexanone giving 1-azaphenanthrene compound 21. Reaction of enamino phosphonium salts 2 with aldehydes 3 gives symmetrical dihydropyridines 5.

  DOI：

  10.1021/jo9902650
• 作为产物：
  描述：

  3-吡啶甲醛 、 4-(Ethoxycarbonyl)-1,1-diphenyl-1-methyl-2-aza-1λ⁵-phosphabuta-1,3-diene 以 氯仿 为溶剂， 反应 2.0h， 以67%的产率得到(E)-3-{[1-Pyridin-3-yl-meth-(E)-ylidene]-amino}-acrylic acid ethyl ester
  参考文献：
  名称：

  Reaction of N-Vinylic Phosphazenes Derived from β-Amino Acids with Aldehydes. Azadiene-Mediated Synthesis of Dihydropyridines, Pyridines, and Polycyclic Nitrogen Derivatives

  摘要：

  Enamino phosphonium salts 2 are obtained by 1,2-addition of hydrogen chloride to N-vinylic phosphazenes 1 derived from triphenylphosphine. Aza-Wittig reaction of phosphazenes 1 derived from triphenylphosphine and 6 derived from diphenylmethylphosphine with aldehydes 3 leads to the formation of 2-azadienes 7. Reaction of azadienes 7 with enamines affords dihydropyridines 9 and 11, pyridines 12, and bicyclic nitrogen heterocycles 15-18 in a regioselective fashion, while heterodiene 20 reacts in the same way with pyrrolidinocyclohexanone giving 1-azaphenanthrene compound 21. Reaction of enamino phosphonium salts 2 with aldehydes 3 gives symmetrical dihydropyridines 5.

  DOI：

  10.1021/jo9902650