ethyl 1-benzhydryl-8-[(E)-but-2-enyl]-5-hydroxy-6-methoxyisoquinoline-3-carboxylate | 133495-80-4

• 分子结构分类: 有机化合物 - 生物碱及其衍生物
• 英文名称: ethyl 1-benzhydryl-8-[(E)-but-2-enyl]-5-hydroxy-6-methoxyisoquinoline-3-carboxylate
• CAS: 133495-80-4
• 化学式: C₃₀H₂₉NO₄
• 分子量: 467.565
• InChiKey: WTAZRUBURXCCQN-GQCTYLIASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  35
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 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：

  Ethyl 5-(crotonyloxy)-1-(diphenylmethyl)-6-methoxyisoquinoline-3-carboxylate 以 甲苯 为溶剂， 反应 16.0h， 以35%的产率得到ethyl 1-benzhydryl-8-[(E)-but-2-enyl]-5-hydroxy-6-methoxyisoquinoline-3-carboxylate
  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

• One-pot preparation of derivatives of the unknown fluoreno[2,3,4-i,j]isoquinoline ring from conjugated ketenimines by a consecutive electrocyclic ring-closure/Claisen rearrangement/intramolecular Diels–Alder cycloaddition/double aromatization process
  作者：Pedro Molina、Mateo Alajarín、Angel Vidal、J. Feneau-Dupont、J. P. Declercq

  DOI：10.1039/c39900000829

  日期：——

  A short synthesis of fluoreno[2,3,4-i,j]isoquinoline derivatives (8) based on a new method of three consecutive annelations which involves thermal cyclization of conjugated ketenimines is described; the crystal structure of (8) has been determined.

  描述了一种基于三步连续化的新方法的氟代[2,3,4- i，j ]异喹啉衍生物（8）的简短合成，该方法涉及共轭酮亚胺的热环化。已经确定了（8）的晶体结构。
• MOLINA, PEDRO;ALAJARIN, MATEO;VIDAL, ANGEL;FENEAU-DUPONT, J.;DECLERCQ, J.+, J. CHEM. SOC. CHEM. COMMUN.,(1990) N1, C. 829-831
  作者：MOLINA, PEDRO、ALAJARIN, MATEO、VIDAL, ANGEL、FENEAU-DUPONT, J.、DECLERCQ, J.+

  DOI：——

  日期：——
• 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：——