ethyl 2-amino-3-bromocyclohex-1-ene-1-carboxylate | 1422271-61-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物
• 英文名称: ethyl 2-amino-3-bromocyclohex-1-ene-1-carboxylate
• CAS: 1422271-61-1
• 化学式: C₉H₁₄BrNO₂
• 分子量: 248.12
• InChiKey: YLTBFVBIRVUSMP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.71
• 重原子数：
  13.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  52.32
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  ethyl 2-amino-3-bromocyclohex-1-ene-1-carboxylate 在 sodium cyanoborohydride 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 以60%的产率得到
  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
• 作为产物：
  描述：

  3-bromo-2-hydroxy-cyclohex-1-enecarboxylic acid ethyl ester 在 氨基甲酸铵 作用下， 以 乙醇 为溶剂， 以96%的产率得到ethyl 2-amino-3-bromocyclohex-1-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