8-fluoro-6,11,11a,12-tetrahydroindolo[1,2-b]isoquinoline | 1597592-93-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: 8-fluoro-6,11,11a,12-tetrahydroindolo[1,2-b]isoquinoline
• 英文别名: 8-Fluoro-6,11,11a,12-tetrahydroindolo[1,2-b]isoquinoline
• CAS: 1597592-93-2
• 化学式: C₁₆H₁₄FN
• 分子量: 239.292
• InChiKey: OLTKOCCBUAKIFC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-allyl-phenylamine 在 tris-(dibenzylideneacetone)dipalladium(0) 、 lithium aluminium tetrahydride 、 tricyclohexylphosphine tetrafluoroborate 、 sodium t-butanolate 作用下， 以 乙醚 、 甲苯 为溶剂， 反应 18.0h， 生成 8-fluoro-6,11,11a,12-tetrahydroindolo[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

文献信息

• Synthesis of Substituted Tetrahydroindoloisoquinoline Derivatives via Intramolecular Pd-Catalyzed Alkene Carboamination Reactions
  作者：Jeremiah Alicea、John P. Wolfe

  DOI：10.1021/jo500470m

  日期：2014.5.2

  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.