2-ethoxycarbonyl-4-(4-methylphenyl)aminobenz[f]isoquinoline | 1315574-36-7

• 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: 2-ethoxycarbonyl-4-(4-methylphenyl)aminobenz[f]isoquinoline
• 英文别名: Ethyl 4-(4-methylanilino)benzo[f]isoquinoline-2-carboxylate；ethyl 4-(4-methylanilino)benzo[f]isoquinoline-2-carboxylate
• CAS: 1315574-36-7
• 化学式: C₂₃H₂₀N₂O₂
• 分子量: 356.424
• InChiKey: XRPWMVRJEXCUFC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  51.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-(1-bromonaphthalen-2-yl)-1,3-dioxolane 在 正丁基锂 、 sodium 作用下， 以 乙醚 、 乙醇 、 正己烷 、 甲苯 为溶剂， 反应 72.75h， 生成 2-ethoxycarbonyl-4-(4-methylphenyl)aminobenz[f]isoquinoline
  参考文献：
  名称：

  retro-Cheletropic ene reactions with 2-carbena-1,3-dioxolane as chelefuge

  摘要：

  N[beta-(Hetero)arylvinyl] ketenimines and carbodiimides bearing adequately positioned 1,3-dioxolane functions experience a new class of tandem process consisting of a 6 pi electrocyclic ring closure followed by a rare retro-cheletropic ene reaction, the extrusion of 2-carbena-1,3-dioxolane. This mechanistic sequence is supported by a computational study using DFT methods, showing that the simultaneous recovery of aromaticity at two rings is the clue for the low energy barrier of the retro-cheletropic step. Moreover, the highly exergonic decomposition of 2-carbena-1,3-dioxolane into CO2 plus ethylene contribute to the success of the tandem sequences. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.05.119

文献信息

• retro-Cheletropic ene reactions with 2-carbena-1,3-dioxolane as chelefuge
  作者：Mateo Alajarin、Marta Marin-Luna、Maria-Mar Ortin、Pilar Sanchez-Andrada、Angel Vidal

  DOI：10.1016/j.tet.2011.05.119

  日期：2011.8

  N[beta-(Hetero)arylvinyl] ketenimines and carbodiimides bearing adequately positioned 1,3-dioxolane functions experience a new class of tandem process consisting of a 6 pi electrocyclic ring closure followed by a rare retro-cheletropic ene reaction, the extrusion of 2-carbena-1,3-dioxolane. This mechanistic sequence is supported by a computational study using DFT methods, showing that the simultaneous recovery of aromaticity at two rings is the clue for the low energy barrier of the retro-cheletropic step. Moreover, the highly exergonic decomposition of 2-carbena-1,3-dioxolane into CO2 plus ethylene contribute to the success of the tandem sequences. (C) 2011 Elsevier Ltd. All rights reserved.