2-bromo-N-(2-methylallyl)-N-(1-phenylvinyl)benzamide | 1333120-22-1

• 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-bromo-N-(2-methylallyl)-N-(1-phenylvinyl)benzamide
• 英文别名: 2-bromo-N-(2-methylprop-2-enyl)-N-(1-phenylethenyl)benzamide
• CAS: 1333120-22-1
• 化学式: C₁₉H₁₈BrNO
• 分子量: 356.262
• InChiKey: PJDNPWPRNICMMA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-bromo-N-(2-methylallyl)-N-(1-phenylvinyl)benzamide 在 Pd(Q-Phos)2 、 potassium iodide 作用下， 以 甲苯 为溶剂， 反应 16.0h， 生成 rac-(2S,9bR)-2-iodomethyl-2-methyl-9b-phenyl-2,3-dihydro-1H-pyrrolo[2,1-a]isoindol-5(9bH)-one 、 rac-(2R,9bR)-2-iodomethyl-2-methyl-9b-phenyl-2,3-dihydro-1H-pyrrolo[2,1-a]isoindol-5(9bH)-one
  参考文献：
  名称：

  Palladium-Catalyzed Carbohalogenation: Bromide to Iodide Exchange and Domino Processes

  摘要：

  Aryl bromides have been used to prepare a variety of nitrogen- and oxygen-containing heterocycles featuring new carbon-carbon and carbon-iodine bonds. This palladium-catalyzed carbohalogenation requires potassium iodide for the reaction to proceed in high yields. Additionally, the first examples of domino carbohalogenation reactions have been demonstrated using both aryl iodide and aryl bromide starting materials. Complex products with multiple rings and stereogenic centers are generated in excellent yields with moderate to excellent diastereoselectivities.

  DOI：

  10.1021/ja206099t
• 作为产物：
  描述：

  2-溴苯甲酸 在 草酰氯 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 2-bromo-N-(2-methylallyl)-N-(1-phenylvinyl)benzamide
  参考文献：
  名称：

  Palladium-Catalyzed Carbohalogenation: Bromide to Iodide Exchange and Domino Processes

  摘要：

  Aryl bromides have been used to prepare a variety of nitrogen- and oxygen-containing heterocycles featuring new carbon-carbon and carbon-iodine bonds. This palladium-catalyzed carbohalogenation requires potassium iodide for the reaction to proceed in high yields. Additionally, the first examples of domino carbohalogenation reactions have been demonstrated using both aryl iodide and aryl bromide starting materials. Complex products with multiple rings and stereogenic centers are generated in excellent yields with moderate to excellent diastereoselectivities.

  DOI：

  10.1021/ja206099t