(Z)-2-Azido-3-[3-methoxy-2-(3-methyl-but-2-enyloxy)-phenyl]-acrylic acid ethyl ester | 133495-70-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (Z)-2-Azido-3-[3-methoxy-2-(3-methyl-but-2-enyloxy)-phenyl]-acrylic acid ethyl ester
• 英文别名: ethyl (Z)-2-azido-3-[3-methoxy-2-(3-methylbut-2-enoxy)phenyl]prop-2-enoate
• CAS: 133495-70-2
• 化学式: C₁₇H₂₁N₃O₄
• 分子量: 331.371
• InChiKey: GLVQBMJPHNHTBO-KAMYIIQDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.25
• 重原子数：
  24.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  93.52
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (Z)-2-Azido-3-[3-methoxy-2-(3-methyl-but-2-enyloxy)-phenyl]-acrylic acid ethyl ester 以 乙醚 、 甲苯 为溶剂， 反应 13.0h， 生成 (Z)-2-Diphenylvinylideneamino-3-[3-methoxy-2-(3-methyl-but-2-enyloxy)-phenyl]-acrylic acid ethyl ester
  参考文献：
  名称：

  Domino reactions. One-pot preparation of fluoreno[2,3,4-ij]isoquinoline derivatives from conjugated ketene imines

  摘要：

  Iminophosphoranes 4, derived from ethyl alpha-azido-2-(allyloxy)-3-methoxycinnamates, react with ketenes to give the corresponding ketene imines, which by thermal treatment at 150-160-degrees-C undergo a consecutive electrocyclic ring closure/Claisen rearrangement/second ring closure/double aromatization process to give isoquinoline derivatives 7 and/or the previously unknown fluoreno[2,3,4-ij]isoquinolines 9 in moderate yields. Similarly, iminophosphoranes 14 derived from ethyl alpha-azido-2,3-disubstituted-4-(allyloxy)cinnamates reacted with diphenyl ketene to give the intermediate ketene imines, which at 150-160-degrees-C undergo a cascade of pericyclic reactions to give the isoquinolines 15 and the pentacyclic compounds 16 in moderate yields.

  DOI：

  10.1021/jo00012a039
• 作为产物：
  描述：

  邻香草醛 在 sodium ethanolate 、 potassium carbonate 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 30.0h， 生成 (Z)-2-Azido-3-[3-methoxy-2-(3-methyl-but-2-enyloxy)-phenyl]-acrylic acid ethyl ester
  参考文献：
  名称：

  Domino reactions. One-pot preparation of fluoreno[2,3,4-ij]isoquinoline derivatives from conjugated ketene imines

  摘要：

  Iminophosphoranes 4, derived from ethyl alpha-azido-2-(allyloxy)-3-methoxycinnamates, react with ketenes to give the corresponding ketene imines, which by thermal treatment at 150-160-degrees-C undergo a consecutive electrocyclic ring closure/Claisen rearrangement/second ring closure/double aromatization process to give isoquinoline derivatives 7 and/or the previously unknown fluoreno[2,3,4-ij]isoquinolines 9 in moderate yields. Similarly, iminophosphoranes 14 derived from ethyl alpha-azido-2,3-disubstituted-4-(allyloxy)cinnamates reacted with diphenyl ketene to give the intermediate ketene imines, which at 150-160-degrees-C undergo a cascade of pericyclic reactions to give the isoquinolines 15 and the pentacyclic compounds 16 in moderate yields.

  DOI：

  10.1021/jo00012a039

文献信息

• MOLINA, PEDRO;ALAJARIN, MATEO;VIDAL, ANGEL;FENAU-DUPONT, J.;DECLERQ, J. P+, J. ORG. CHEM., 56,(1991) N2, C. 4008-4016
  作者：MOLINA, PEDRO、ALAJARIN, MATEO、VIDAL, ANGEL、FENAU-DUPONT, J.、DECLERQ, J. P+

  DOI：——

  日期：——