N-(3’-chlorobutyl)-4-toluenesulfonamide | 1451062-68-2

• 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-(3’-chlorobutyl)-4-toluenesulfonamide
• 英文别名: N-(3-chlorobutyl)-4-methylbenzenesulfonamide
• CAS: 1451062-68-2
• 化学式: C₁₁H₁₆ClNO₂S
• 分子量: 261.773
• InChiKey: WWPIAYHPSKUHSE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  54.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-(3-丁烯-1-基)-4-甲基苯磺酰胺 在 iron(III) chloride 、 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate 作用下， 反应 24.0h， 以82%的产率得到N-(3’-chlorobutyl)-4-toluenesulfonamide
  参考文献：
  名称：

  An Effective Procedure to Promote Aza–Prins Cyclization Reactions Employing a Combination of Ferric Chloride and an Imidazolium Salt in Benzotrifluoride

  摘要：

  Aza-Prins cyclization reactions of N-tosyl-3-butenylamine with p-methoxybenzaldehyde, 1-naphthaldehyde and 2-naphthaldehyde take place efficiently using a combination 1-butyl-3-methylimidazolium of ferric chloride and hexafluorophosphate in benzotrifluoride (Felm-BTF procedure). The new methodology, leading to formation of target N-tosyl-4-chloro-2-substituted piperidines, is superior to the one using 1-butyl-3-methylimidazolium tetrachloroferrate. The Felm-BTF procedure was also applied to aza-Prins cyclization reactions of other aldehydes. Finally, the effects of imidazolium salts on aza-Prins cyclization reaction promoted by boranetrifluoride-diethyl ether complex, leading to formation of fluorinated piperidines, were explored.

  DOI：

  10.3987/com-12-s(n)78

文献信息

• An Effective Procedure to Promote Aza–Prins Cyclization Reactions Employing a Combination of Ferric Chloride and an Imidazolium Salt in Benzotrifluoride
  作者：Eietsu Hasegawa、Chika Osawa、Minami Tateyama、Kensuke Miura、Eiji Tayama、Hajime Iwamoto

  DOI：10.3987/com-12-s(n)78

  日期：——

  Aza-Prins cyclization reactions of N-tosyl-3-butenylamine with p-methoxybenzaldehyde, 1-naphthaldehyde and 2-naphthaldehyde take place efficiently using a combination 1-butyl-3-methylimidazolium of ferric chloride and hexafluorophosphate in benzotrifluoride (Felm-BTF procedure). The new methodology, leading to formation of target N-tosyl-4-chloro-2-substituted piperidines, is superior to the one using 1-butyl-3-methylimidazolium tetrachloroferrate. The Felm-BTF procedure was also applied to aza-Prins cyclization reactions of other aldehydes. Finally, the effects of imidazolium salts on aza-Prins cyclization reaction promoted by boranetrifluoride-diethyl ether complex, leading to formation of fluorinated piperidines, were explored.