2-allyl-N-[(2-bromocyclohex-1-en-1-yl)methyl]aniline | 1597592-72-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-allyl-N-[(2-bromocyclohex-1-en-1-yl)methyl]aniline
• CAS: 1597592-72-7
• 化学式: C₁₆H₂₀BrN
• 分子量: 306.245
• InChiKey: CNBSDVPCTGLZOQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.05
• 重原子数：
  18.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  12.03
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  2-allyl-N-[(2-bromocyclohex-1-en-1-yl)methyl]aniline 在 tris-(dibenzylideneacetone)dipalladium(0) 、 tricyclohexylphosphine tetrafluoroborate 、 sodium t-butanolate 作用下， 以 甲苯 为溶剂， 反应 18.0h， 以55%的产率得到6,7,8,9,10,11,11a,12-octahydroindolo[1,2-b]isoquinoline
  参考文献：
  名称：

  Synthesis of Substituted Tetrahydroindoloisoquinoline Derivatives via Intramolecular Pd-Catalyzed Alkene Carboamination Reactions

  摘要：

  Intramolecular Pd-catalyzed alkene carboamination reactions of substituted 2-allyl-N-(2-bromobenzyl)anilines are described. The substrates for these reactions are generated in two steps from readily available 2-allylanilines and 2-bromobenzaldehyde derivatives. The transformations afford substituted tetrahydroindoloisoquinolines, an uncommon class of fused bicyclic heterocycles, in good yield. The mechanism of these transformations is described, and a model that accounts for the observed product stereochemistry is proposed.

  DOI：

  10.1021/jo500470m
• 作为产物：
  描述：

  2-溴-1-环己烯-1-甲醛 在 lithium aluminium tetrahydride 作用下， 以 乙醚 、 甲苯 为溶剂， 生成 2-allyl-N-[(2-bromocyclohex-1-en-1-yl)methyl]aniline
  参考文献：
  名称：

  Synthesis of Substituted Tetrahydroindoloisoquinoline Derivatives via Intramolecular Pd-Catalyzed Alkene Carboamination Reactions

  摘要：

  Intramolecular Pd-catalyzed alkene carboamination reactions of substituted 2-allyl-N-(2-bromobenzyl)anilines are described. The substrates for these reactions are generated in two steps from readily available 2-allylanilines and 2-bromobenzaldehyde derivatives. The transformations afford substituted tetrahydroindoloisoquinolines, an uncommon class of fused bicyclic heterocycles, in good yield. The mechanism of these transformations is described, and a model that accounts for the observed product stereochemistry is proposed.

  DOI：

  10.1021/jo500470m