Ethyl 5,5-dimethyl-1-hydroxy-2-methoxy-9b-phenyl-4a,9b-dihydro-4H-fluoreno<2,3,4-ij>isoquinoline-11-carboxylate | 133495-83-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: Ethyl 5,5-dimethyl-1-hydroxy-2-methoxy-9b-phenyl-4a,9b-dihydro-4H-fluoreno<2,3,4-ij>isoquinoline-11-carboxylate
• CAS: 133495-83-7
• 化学式: C₃₁H₂₉NO₄
• 分子量: 479.576
• InChiKey: UDQKUXATZXFRKY-VVFBEHOQSA-N

反应信息

• 作为产物：
  描述：

  (Z)-2-Diphenylvinylideneamino-3-[3-methoxy-2-(3-methyl-but-2-enyloxy)-phenyl]-acrylic acid ethyl ester 以 甲苯 为溶剂， 反应 16.0h， 以29%的产率得到1-Benzhydryl-5-hydroxy-6-methoxy-8-(3-methyl-but-2-enyl)-isoquinoline-3-carboxylic 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