ethyl 1,2,6,7,8,8a-hexahydro-1-(4-nitrophenyl)-4-isoquinolinecarboxylate | 244239-09-6

• 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: ethyl 1,2,6,7,8,8a-hexahydro-1-(4-nitrophenyl)-4-isoquinolinecarboxylate
• 英文别名: Ethyl 1-(4-nitrophenyl)-1,2,6,7,8,8a-hexahydroisoquinoline-4-carboxylate
• CAS: 244239-09-6
• 化学式: C₁₈H₂₀N₂O₄
• 分子量: 328.368
• InChiKey: XJQWFWWYUDHZNW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  84.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 1,2,6,7,8,8a-hexahydro-1-(4-nitrophenyl)-4-isoquinolinecarboxylate 在 对苯醌 作用下， 以 1,4-二氧六环 为溶剂， 反应 14.0h， 以90%的产率得到Ethyl 1-(4-nitrophenyl)-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：

  4-(Ethoxycarbonyl)-1,1-diphenyl-1-methyl-2-aza-1λ⁵-phosphabuta-1,3-diene 以 氯仿 为溶剂， 反应 3.0h， 生成 ethyl 1,2,6,7,8,8a-hexahydro-1-(4-nitrophenyl)-4-isoquinolinecarboxylate
  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

文献信息

• Reaction of <i>N</i>-Vinylic Phosphazenes Derived from β-Amino Acids with Aldehydes. Azadiene-Mediated Synthesis of Dihydropyridines, Pyridines, and Polycyclic Nitrogen Derivatives
  作者：Francisco Palacios、Esther Herrán、Gloria Rubiales

  DOI：10.1021/jo9902650

  日期：1999.8.1

  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.