ethyl 2-azido-3-[2-(1,3-dioxolan-2-yl)-1-naphthyl]propenoate | 1315574-33-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: ethyl 2-azido-3-[2-(1,3-dioxolan-2-yl)-1-naphthyl]propenoate
• CAS: 1315574-33-4
• 化学式: C₁₈H₁₇N₃O₄
• 分子量: 339.351
• InChiKey: DWZSEBGXGBJWPO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  25.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  93.52
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  ethyl 2-azido-3-[2-(1,3-dioxolan-2-yl)-1-naphthyl]propenoate 以 乙醚 、 甲苯 为溶剂， 反应 17.0h， 生成
  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
• 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 为溶剂， 反应 31.75h， 生成 ethyl 2-azido-3-[2-(1,3-dioxolan-2-yl)-1-naphthyl]propenoate
  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