ethyl 2-(2-chlorophenyl)indolizine-1-carboxylate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: ethyl 2-(2-chlorophenyl)indolizine-1-carboxylate
• 化学式: C₁₇H₁₄ClNO₂
• 分子量: 299.757
• InChiKey: PNHPFUYVUSWNHH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  30.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-吡啶乙酸乙酯 、 邻氯苯乙酮 在 二叔丁基过氧化物 、 碘 、 copper(ll) bromide 作用下， 反应 5.0h， 以70%的产率得到ethyl 2-(2-chlorophenyl)indolizine-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.