4-chloro-N-[2,2-dichloro-1-(4-methylphenyl)-2-phenylethyl]benzenesulfonamide | 429619-19-2

• 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: 4-chloro-N-[2,2-dichloro-1-(4-methylphenyl)-2-phenylethyl]benzenesulfonamide
• 英文别名: N-[2,2-dichloro-1-(4-methylphenyl)-2-phenylethyl]-4-chlorobenzenesulfonamide；4-chloro-N-[2,2-dichloro-1-(4-methylphenyl)-2-phenylethyl]benzenesulfon-amide
• CAS: 429619-19-2
• 化学式: C₂₁H₁₈Cl₃NO₂S
• 分子量: 454.804
• InChiKey: AQFNAJMGARQDTR-UHFFFAOYSA-N

物化性质

• 沸点：
  564.4±60.0 °C(Predicted)
• 密度：
  1.375±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  54.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-chloro-N-[2,2-dichloro-1-(4-methylphenyl)-2-phenylethyl]benzenesulfonamide 在 sodium carbonate 、 硫脲 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以25%的产率得到2-chloro-1-(4-chlorophenylsulfonyl)-2-(4-methylphenyl)-3-phenylaziridine
  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：

  N,N-dichloro-4-chlorobenzenesulfonamide 在 硫酸 作用下， 反应 5.0h， 生成 4-chloro-N-[2,2-dichloro-1-(4-methylphenyl)-2-phenylethyl]benzenesulfonamide
  参考文献：
  名称：

  摘要：

  Benzene, toluene, and 2-chlorothiophene regioselectively react with N-(2,2-dichloro-2-phenylethylidene)arenesulfonamides in the presence of oleum to give N-[1-aryl(or hetaryl)-2,2-dichloro-2-phenylethyl]arenesulfonamides. Analogous C-amidoalkylation products are formed by the action of N-(2,2-dichloro-1-hydroxy-2-phenylethyl)- and N-(1-arylsulfonylamino-2,2-dichloro-2-phenylethyl)arenesulfonamides on toluene and 2-chlorothiophene in concentrated sulfuric acid.

  DOI：

  10.1023/a:1013135722293

文献信息

• Amidine derivatives of α-arylglycines from N-(1-aryl-2,2,2-trichloroethyl)amides of arenesulfonic acids and secondary amines
  作者：Igor B. Rozentsveig、Galina G. Levkovskaya、Gulnur N. Rozentsveig、Anna N. Mirskova、Leonid B. Krivdin、Ludmila I. Larina、Aleksandr I. Albanov

  DOI：10.1016/j.tetlet.2005.10.079

  日期：2005.12

  The interaction of N-(1-aryl-2,2,2-trichloroethyl)amides of arenesulfonic acids with secondary amines or their salts in the presence of inorganic bases involves the formation of chloroaziridine intermediates. Depending upon the solvent and reagent ratio, the reaction results in N-[1-dialkylamino-2-chloro-2-arylethylidene]-, N-[2-dialkylamino-1-chloro-2-arylethylidene]-, N-[1,2-bis(dialkylamino)-2-arylethylidene]-

  的相互作用ñ -的芳烃磺酸与无机碱的存在下仲胺或它们的盐的酰胺（1-芳基2,2,2-三氯乙基）涉及chloroaziridine中间体的形成。根据溶剂和试剂的比例，反应产生N- [1-二烷基氨基-2-氯-2-芳基亚乙基]-，N- [2-二烷基氨基-1-氯-2-芳基亚乙基]-，N- [1芳烃磺酸的-，2-双（二烷基氨基）-2-芳基亚乙基]-和N-（1,2-二氧代-2-芳基乙烯）酰胺。
• 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