6-Bromo-3-vinyl-hept-6-enal | 151654-86-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-Bromo-3-vinyl-hept-6-enal
• CAS: 151654-86-3
• 化学式: C₉H₁₃BrO
• 分子量: 217.106
• InChiKey: LZYUDWXTUQHJBU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.07
• 重原子数：
  11.0
• 可旋转键数：
  6.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  6-Bromo-3-vinyl-hept-6-enal 在 palladium diacetate 4 A molecular sieve 、 sodium cyanoborohydride 、 三乙胺 、 三(邻甲基苯基)磷 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 14.0h， 生成 (3aR,6aS)-1-Benzyl-6a-methyl-6-methylene-octahydro-cyclopenta[b]pyrrole
  参考文献：
  名称：

  Synthesis of bicyclic nitrogen compounds via tandem intramolecular Heck cyclization and subsequent trapping of intermediate .pi.-allylpalladium complexes

  摘要：

  Intramolecular palladium-mediated three-component cyclizations of substrates containing vinyl halide, olefin, and sulfonamide moieties to generate a diverse group of nitrogen heterocycles have been developed. The methodology has been applied to construction of both fused and bridged bicyclic systems. The strategy can also be used for spirocyclizations. This chemistry involves regiospecific generation of pi-allylpalladium complexes via Heck reactions of vinyl halides and simple olefins, followed by nucleophilic addition of sulfonamide anions to these intermediates.

  DOI：

  10.1021/jo00072a030
• 作为产物：
  描述：

  6-Bromo-3-((E)-2-ethoxy-vinyl)-hept-6-en-1-ol 以 various solvent(s) 为溶剂， 反应 17.0h， 以87%的产率得到6-Bromo-3-vinyl-hept-6-enal
  参考文献：
  名称：

  Synthesis of bicyclic nitrogen compounds via tandem intramolecular Heck cyclization and subsequent trapping of intermediate .pi.-allylpalladium complexes

  摘要：

  Intramolecular palladium-mediated three-component cyclizations of substrates containing vinyl halide, olefin, and sulfonamide moieties to generate a diverse group of nitrogen heterocycles have been developed. The methodology has been applied to construction of both fused and bridged bicyclic systems. The strategy can also be used for spirocyclizations. This chemistry involves regiospecific generation of pi-allylpalladium complexes via Heck reactions of vinyl halides and simple olefins, followed by nucleophilic addition of sulfonamide anions to these intermediates.

  DOI：

  10.1021/jo00072a030