8-Allyl-1-benzhydryl-5-benzyloxy-6-methoxy-isoquinoline-3-carboxylic acid ethyl ester | 133522-74-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 8-Allyl-1-benzhydryl-5-benzyloxy-6-methoxy-isoquinoline-3-carboxylic acid ethyl ester
• 英文别名: Ethyl 1-benzhydryl-6-methoxy-5-phenylmethoxy-8-prop-2-enylisoquinoline-3-carboxylate
• CAS: 133522-74-4
• 化学式: C₃₆H₃₃NO₄
• 分子量: 543.662
• InChiKey: ULRDMAPEXLNNKE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.6
• 重原子数：
  41
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  57.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  ethyl α-<(triphenylphosphoranylidene)amino>-5-allyl-2-(benzyloxy)-3-methoxycinnamate 以 甲苯 为溶剂， 反应 17.0h， 生成 8-Allyl-1-benzhydryl-5-benzyloxy-6-methoxy-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

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：——