(Z)-6,7-dimethoxy-2-carbethoxy-1-(2-nitrobenzylidene)-1,2,3,4-tetrahydroisoquinoline | 1262335-18-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: (Z)-6,7-dimethoxy-2-carbethoxy-1-(2-nitrobenzylidene)-1,2,3,4-tetrahydroisoquinoline
• 英文别名: ethyl (1Z)-6,7-dimethoxy-1-[(2-nitrophenyl)methylidene]-3,4-dihydroisoquinoline-2-carboxylate
• CAS: 1262335-18-1
• 化学式: C₂₁H₂₂N₂O₆
• 分子量: 398.415
• InChiKey: JGDQUSQPTIXLMG-WQRHYEAKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  93.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (Z)-6,7-dimethoxy-2-carbethoxy-1-(2-nitrobenzylidene)-1,2,3,4-tetrahydroisoquinoline 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以55%的产率得到3-(4,5-dimethoxy-2-vinylphenyl)-5-nitro-2Hisoquinolin-1-one
  参考文献：
  名称：

  (Z)-Ethyl 2-phenyl-1-(2-vinylphenyl)vinylcarbamates. Part 1: Synthesis and preliminary studies on their divergent transformation into benzo[c]phenanthridines and 2-phenyl-1,4-naphthoquinones

  摘要：

  Treatment of N-carbethoxy-1-benzylideneisoquinolines with LDA gives N-ethoxycarbonyl-1-amino-1-(2-vinylphenyl)-2-phenylethylenes, which can easily be transformed into N-carbethoxy-1-amino-2-phenylnaphthalenes. Bischler-Napieralski reaction of these latter compounds affords the corresponding benzo[c]phenanthridines, while their hydrolysis and subsequent oxidation constitutes a novel route to 2-phenyl-1,4-naphthoquinones. (c) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.10.035
• 作为产物：
  描述：

  6,7-dimethoxy-1-(2-nitro-benzyl)-3,4-dihydro-isoquinoline 、 氯甲酸乙酯 在 sodium carbonate 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 2.5h， 以44%的产率得到(Z)-6,7-dimethoxy-2-carbethoxy-1-(2-nitrobenzylidene)-1,2,3,4-tetrahydroisoquinoline
  参考文献：
  名称：

  (Z)-Ethyl 2-phenyl-1-(2-vinylphenyl)vinylcarbamates. Part 1: Synthesis and preliminary studies on their divergent transformation into benzo[c]phenanthridines and 2-phenyl-1,4-naphthoquinones

  摘要：

  Treatment of N-carbethoxy-1-benzylideneisoquinolines with LDA gives N-ethoxycarbonyl-1-amino-1-(2-vinylphenyl)-2-phenylethylenes, which can easily be transformed into N-carbethoxy-1-amino-2-phenylnaphthalenes. Bischler-Napieralski reaction of these latter compounds affords the corresponding benzo[c]phenanthridines, while their hydrolysis and subsequent oxidation constitutes a novel route to 2-phenyl-1,4-naphthoquinones. (c) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.10.035

文献信息

• (Z)-Ethyl 2-phenyl-1-(2-vinylphenyl)vinylcarbamates. Part 1: Synthesis and preliminary studies on their divergent transformation into benzo[c]phenanthridines and 2-phenyl-1,4-naphthoquinones
  作者：Mónica Treus、Cristian O. Salas、Marcos A. Gonazález、Juan C. Estévez、Ricardo A. Tapia、Ramón J. Estévez

  DOI：10.1016/j.tet.2010.10.035

  日期：2010.12

  Treatment of N-carbethoxy-1-benzylideneisoquinolines with LDA gives N-ethoxycarbonyl-1-amino-1-(2-vinylphenyl)-2-phenylethylenes, which can easily be transformed into N-carbethoxy-1-amino-2-phenylnaphthalenes. Bischler-Napieralski reaction of these latter compounds affords the corresponding benzo[c]phenanthridines, while their hydrolysis and subsequent oxidation constitutes a novel route to 2-phenyl-1,4-naphthoquinones. (c) 2010 Elsevier Ltd. All rights reserved.