N-benzyl-3-bromo-N-(2,3-dimethylbut-2-enyl)benzenesulfonamide

• 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: N-benzyl-3-bromo-N-(2,3-dimethylbut-2-enyl)benzenesulfonamide
• 英文别名: N-benzyl-3-bromo-N-(2,3-dimethylbut-2-enyl)lbenzenesulfonamide
• 化学式: C₁₉H₂₂BrNO₂S
• 分子量: 408.359
• InChiKey: IRVIDVBVLCVIDE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-benzyl-3-bromo-N-(2,3-dimethylbut-2-enyl)benzenesulfonamide 在 三乙基硅烷 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以94%的产率得到N-苄基-3-溴苯磺酰胺
  参考文献：
  名称：

  Methylprenyl and Prenyl Protection for Sulfonamides

  摘要：

  2-Methylprenyl (MePre) is an efficient protection for sulfonamides. The acidic cleavage of this group leads to volatile by-products and the product can be obtained in high purity without additional purification. MePre group is resistant to Pd/C-catalysed hydrogenolysis at 1 atm, Suzuki-Miyaura reaction, Ni(0) catalysis conditions and oxidising reagents such as NIS and DDQ. The prenyl (Pre) group can also be used to protect sulfonamides in certain cases; however, the substrate scope is limited due to the side product formation.

  DOI：

  10.1055/s-0034-1379428
• 作为产物：
  描述：

  3-溴苯磺酰氯 在 碳酸氢钠 、 caesium carbonate 作用下， 以 1,4-二氧六环 为溶剂， 反应 3.0h， 生成 N-benzyl-3-bromo-N-(2,3-dimethylbut-2-enyl)benzenesulfonamide
  参考文献：
  名称：

  Methylprenyl and Prenyl Protection for Sulfonamides

  摘要：

  2-Methylprenyl (MePre) is an efficient protection for sulfonamides. The acidic cleavage of this group leads to volatile by-products and the product can be obtained in high purity without additional purification. MePre group is resistant to Pd/C-catalysed hydrogenolysis at 1 atm, Suzuki-Miyaura reaction, Ni(0) catalysis conditions and oxidising reagents such as NIS and DDQ. The prenyl (Pre) group can also be used to protect sulfonamides in certain cases; however, the substrate scope is limited due to the side product formation.

  DOI：

  10.1055/s-0034-1379428

文献信息

• Methylprenyl and Prenyl Protection for Sulfonamides
  作者：Aigars Jirgensons、Anna Nikitjuka、Aleksandra Nekrasova

  DOI：10.1055/s-0034-1379428

  日期：——

  2-Methylprenyl (MePre) is an efficient protection for sulfonamides. The acidic cleavage of this group leads to volatile by-products and the product can be obtained in high purity without additional purification. MePre group is resistant to Pd/C-catalysed hydrogenolysis at 1 atm, Suzuki-Miyaura reaction, Ni(0) catalysis conditions and oxidising reagents such as NIS and DDQ. The prenyl (Pre) group can also be used to protect sulfonamides in certain cases; however, the substrate scope is limited due to the side product formation.