苯磺酰胺,N-[2-(1-溴乙烯基)-5-己烯基]-4-甲基- | 139705-49-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 苯磺酰胺,N-[2-(1-溴乙烯基)-5-己烯基]-4-甲基-
• 英文名称: N-[2-(1-bromoethenyl)hex-5-enyl]-4-methylbenzenesulfonamide
• CAS: 139705-49-0
• 化学式: C₁₅H₂₀BrNO₂S
• 分子量: 358.299
• InChiKey: OLLLAISXXBNDJS-UHFFFAOYSA-N

物化性质

• 沸点：
  458.5±55.0 °C(Predicted)
• 密度：
  1.300±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.76
• 重原子数：
  20.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  46.17
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  苯磺酰胺,N-[2-(1-溴乙烯基)-5-己烯基]-4-甲基- 在 palladium diacetate 四丁基氯化铵 、 sodium carbonate 、 三(邻甲基苯基)磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以49%的产率得到1-Methyl-7-methylene-2-(toluene-4-sulfonyl)-2-aza-bicyclo[2.2.1]heptane
  参考文献：
  名称：

  A palladium-mediated approach to construction of nitrogen heterocycles

  摘要：

  Sequential regiospecific C-C and C-N bond-forming reactions via a novel variation of the Heck reaction can be used to synthesize nitrogen-containing heterocyclic systems.

  DOI：

  10.1021/jo00035a006
• 作为产物：
  描述：

  1-庚烯-6-炔 在 sodium hydroxide 、 正丁基锂 、 偶氮二甲酸二异丙酯 、 双氧水 、 溶剂黄146 、 9-bromo-9-borabicyclo[3.3.1]nonane 、 三苯基膦 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 苯磺酰胺,N-[2-(1-溴乙烯基)-5-己烯基]-4-甲基-
  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

文献信息

• Synthesis of bicyclic nitrogen compounds via tandem intramolecular Heck cyclization and subsequent trapping of intermediate .pi.-allylpalladium complexes
  作者：G. Davis Harris、R. Jason Herr、Steven M. Weinreb

  DOI：10.1021/jo00072a030

  日期：1993.9

  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.
• A palladium-mediated approach to construction of nitrogen heterocycles
  作者：G. Davis Harris、R. Jason Herr、Steven M. Weinreb

  DOI：10.1021/jo00035a006

  日期：1992.4

  Sequential regiospecific C-C and C-N bond-forming reactions via a novel variation of the Heck reaction can be used to synthesize nitrogen-containing heterocyclic systems.