ethyl 3-(4-chlorobenzoyl)-2-phenylindolizine-1-carboxylate

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 3-(4-chlorobenzoyl)-2-phenylindolizine-1-carboxylate
• 英文别名: Ethyl 3-(4-chlorobenzoyl)-2-phenyl-1-indolizinecarboxylate
• 化学式: C₂₄H₁₈ClNO₃
• 分子量: 403.865
• InChiKey: FZTWJIDOQOHOFM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  47.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-吡啶乙酸乙酯 、 4'-chlorochalcone 在 iron(II) chloride tetrahydrate 、 copper diacetate 作用下， 以 邻二氯苯 为溶剂， 反应 12.0h， 以77%的产率得到ethyl 3-(4-chlorobenzoyl)-2-phenylindolizine-1-carboxylate
  参考文献：
  名称：

  Synthesis of Indolizines through Oxidative Linkage of C–C and C–N Bonds from 2-Pyridylacetates

  摘要：

  Synthesis of indolizine-1-carboxylates through the Ortoleva-King reaction of 2-pyridylacetate followed by the Aldol condensation under mild reaction conditions has been described. This protocol is compatible with a broad range of functional groups, and it has been also successfully extended to unsaturated ketones, bringing about the regioselective formation of benzoyl-substituted indolizines through Michael addition followed by C-N bond formation, which are difficult to prepare by previous methods in a single step.

  DOI：

  10.1021/acs.joc.5b00477

文献信息

• Synthesis of Indolizines through Oxidative Linkage of C–C and C–N Bonds from 2-Pyridylacetates
  作者：Darapaneni Chandra Mohan、Chitrakar Ravi、Venkatanarayana Pappula、Subbarayappa Adimurthy

  DOI：10.1021/acs.joc.5b00477

  日期：2015.7.2

  Synthesis of indolizine-1-carboxylates through the Ortoleva-King reaction of 2-pyridylacetate followed by the Aldol condensation under mild reaction conditions has been described. This protocol is compatible with a broad range of functional groups, and it has been also successfully extended to unsaturated ketones, bringing about the regioselective formation of benzoyl-substituted indolizines through Michael addition followed by C-N bond formation, which are difficult to prepare by previous methods in a single step.