8-((E)-But-2-enyl)-1-di-p-tolylmethyl-5-hydroxy-6-methoxy-isoquinoline-3-carboxylic acid ethyl ester | 133495-86-0

• 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-((E)-But-2-enyl)-1-di-p-tolylmethyl-5-hydroxy-6-methoxy-isoquinoline-3-carboxylic acid ethyl ester
• 英文别名: ethyl 1-[bis(4-methylphenyl)methyl]-8-[(E)-but-2-enyl]-5-hydroxy-6-methoxyisoquinoline-3-carboxylate
• CAS: 133495-86-0
• 化学式: C₃₂H₃₃NO₄
• 分子量: 495.618
• InChiKey: CCXILOWCCYTJNM-SOFGYWHQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  37
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  68.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (Z)-3-{2-[((E)-But-2-enyl)oxy]-3-methoxy-phenyl}-2-di-p-tolylvinylideneamino-acrylic acid ethyl ester 以20%的产率得到
  参考文献：
  名称：

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

  摘要：

  DOI：

文献信息

• Domino reactions. One-pot preparation of fluoreno[2,3,4-ij]isoquinoline derivatives from conjugated ketene imines
  作者：Pedro Molina、Mateo Alajarin、Angel Vidal、J. Fenau-Dupont、J. P. Declerq

  DOI：10.1021/jo00012a039

  日期：1991.6

  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.