ethyl 2-pyrrol-1-ylcyclohex-2-ene-1-carboxylate | 1422271-55-3

• 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-pyrrol-1-ylcyclohex-2-ene-1-carboxylate
• 英文别名: Ethyl 2-pyrrol-1-ylcyclohex-2-ene-1-carboxylate
• CAS: 1422271-55-3
• 化学式: C₁₃H₁₇NO₂
• 分子量: 219.283
• InChiKey: WRUFJJVYQMRGQU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  31.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-环己酮甲酸乙酯 在 4-氯吡啶 、 盐酸 、 氨基甲酸铵 作用下， 以 1,4-二氧六环 、 甲醇 、 水 为溶剂， 生成 Ethyl 2-pyrrol-1-ylcyclohexene-1-carboxylate 、 ethyl 2-pyrrol-1-ylcyclohex-2-ene-1-carboxylate
  参考文献：
  名称：

  An unusual boron tribromide-mediated, one-pot bromination/cyclization reaction. Application to the synthesis of a highly strained cyclopenta[1,3]cyclopropa[1,2-b]pyrrolizin-8-one

  摘要：

  Performing Jefford's cyclization of ethyl 2-pyrrol-1-ylcyclohex-2-ene-1-carboxylate (5) using boron tribromide in refluxing dichloromethane led to a trans-cis bromopyrrolohydrindolone 7 whose debromination in alkaline medium afforded a highly strained cyclopenta[1,3]cyclopropa[1,2-b]pyrrolizin-8-one 6. Compound 7 and two of its diastereoisomers were synthesized in order to better understand this unusual reaction and more generally the reactivity of these systems. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.12.056

文献信息

• An unusual boron tribromide-mediated, one-pot bromination/cyclization reaction. Application to the synthesis of a highly strained cyclopenta[1,3]cyclopropa[1,2-b]pyrrolizin-8-one
  作者：Jean-Pierre Jourdan、Christophe Rochais、Remi Legay、Jana Sopkova de Oliveira Santos、Patrick Dallemagne

  DOI：10.1016/j.tetlet.2012.12.056

  日期：2013.2

  Performing Jefford's cyclization of ethyl 2-pyrrol-1-ylcyclohex-2-ene-1-carboxylate (5) using boron tribromide in refluxing dichloromethane led to a trans-cis bromopyrrolohydrindolone 7 whose debromination in alkaline medium afforded a highly strained cyclopenta[1,3]cyclopropa[1,2-b]pyrrolizin-8-one 6. Compound 7 and two of its diastereoisomers were synthesized in order to better understand this unusual reaction and more generally the reactivity of these systems. (C) 2013 Elsevier Ltd. All rights reserved.