N-[1-(4-methoxyphenyl)-2-phenyl-2,2-dichloroethyl]parachlorophenylsulfonamide | 401516-39-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: N-[1-(4-methoxyphenyl)-2-phenyl-2,2-dichloroethyl]parachlorophenylsulfonamide
• 英文别名: 4-chloro-N-[2,2-dichloro-1-(4-methoxyphenyl)-2-phenylethyl]benzenesulfonamide
• CAS: 401516-39-0
• 化学式: C₂₁H₁₈Cl₃NO₃S
• 分子量: 470.804
• InChiKey: WVFMWRXZRFQMST-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  63.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-[1-(4-methoxyphenyl)-2-phenyl-2,2-dichloroethyl]parachlorophenylsulfonamide 在 sodium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以54%的产率得到4-chloro-N-[2-chloro-2-(4-methoxyphenyl)-1-phenylethenyl]benzenesulfonamide
  参考文献：
  名称：

  Cascade synthesis of 2-amino-5-(4-methoxyphenyl)-4-phenyl-1,3-thiazole by reaction of 4-chloro-N-[2,2-dichloro-1-(4-methoxyphenyl)-2-phenylethyl]benzenesulfonamide with thiourea

  摘要：

  4-Chloro-N-[2,2-dichloro-1-(4-methoxyphenyl)-2-phenylethyl]benzenesulfonamide reacted with thiourea on heating in DMF in the presence of sodium carbonate to give 5-(4-methoxyphenyl)-4-phenyl-1,3-thiazole-2-amine. A probable reaction scheme includes cyclization of the initial N-dichloroethyl amide to N-sulfonyl-2,3-diaryl-2-chloroaziridine which undergoes isomerization with opening of the three-membered ring to 1-arylsulfonylamino-2-chloro-2-(4-methoxyphenyl)-1-phenylethene. The subsequent heterocyclization in the reaction with thiourea is accompanied by aromatization via elimination of the arenesulfonamide fragment.

  DOI：

  10.1134/s1070428011040178
• 作为产物：
  描述：

  苯甲醚 、 1,1-dichloro-2,2-bis(4-chlorophenylsulfonylamino)-1-phenylethane 在 硫酸 作用下， 反应 12.0h， 以75%的产率得到N-[1-(4-methoxyphenyl)-2-phenyl-2,2-dichloroethyl]parachlorophenylsulfonamide
  参考文献：
  名称：

  摘要：

  N-[1-4-Methoxyphenyl-2-phenyl-2,2-dichloroethyl]arenesulfonamides are formed in reaction of N-(2-phenyl,-2.2-dichloroethylidene)-4-chlorobenzenesulfonamide and N-(2-phenyl-2,2-dichloroethylidene)-4-methylbenzenesulfonamide with anisole catalyzed by boron trifluoride etherate, and in reaction of anisole with 1,1-di(arenesulfonamido)-2-phenyl-2,2,-dichloroethanes in the presence of concentrated sulfuric acid.

  DOI：

  10.1023/a:1012457430488

文献信息

• Arylsulfonylaziridines and Arylsulfonylaminoethenes from N-(1-Aryl-2,2-dichloro-2-phenylethyl)arenesulfonamides
  作者：G. N. Rozentsveig、I. B. Rozentsveig、G. G. Levkovskaya、A. I. Albanov、A. N. Mirskova

  DOI：10.1023/b:rujo.0000019749.34777.6f

  日期：2003.12
• ——
  作者：T. I. Drozdova、A. N. Mirskova

  DOI：10.1023/a:1012457430488

  日期：——

  N-[1-4-Methoxyphenyl-2-phenyl-2,2-dichloroethyl]arenesulfonamides are formed in reaction of N-(2-phenyl,-2.2-dichloroethylidene)-4-chlorobenzenesulfonamide and N-(2-phenyl-2,2-dichloroethylidene)-4-methylbenzenesulfonamide with anisole catalyzed by boron trifluoride etherate, and in reaction of anisole with 1,1-di(arenesulfonamido)-2-phenyl-2,2,-dichloroethanes in the presence of concentrated sulfuric acid.
• Cascade synthesis of 2-amino-5-(4-methoxyphenyl)-4-phenyl-1,3-thiazole by reaction of 4-chloro-N-[2,2-dichloro-1-(4-methoxyphenyl)-2-phenylethyl]benzenesulfonamide with thiourea
  作者：G. N. Rozentsveig、V. Yu. Serykh、K. A. Chernyshev、I. B. Rozentsveig、G. G. Levkovskaya、L. B. Krivdin

  DOI：10.1134/s1070428011040178

  日期：2011.4

  4-Chloro-N-[2,2-dichloro-1-(4-methoxyphenyl)-2-phenylethyl]benzenesulfonamide reacted with thiourea on heating in DMF in the presence of sodium carbonate to give 5-(4-methoxyphenyl)-4-phenyl-1,3-thiazole-2-amine. A probable reaction scheme includes cyclization of the initial N-dichloroethyl amide to N-sulfonyl-2,3-diaryl-2-chloroaziridine which undergoes isomerization with opening of the three-membered ring to 1-arylsulfonylamino-2-chloro-2-(4-methoxyphenyl)-1-phenylethene. The subsequent heterocyclization in the reaction with thiourea is accompanied by aromatization via elimination of the arenesulfonamide fragment.