N'-(4-methylphenyl)sulfonyl-N-(2,3,5,6-tetrachloro-4-oxocyclohexa-2,5-dien-1-ylidene)benzenecarboximidamide | 308292-17-3

• 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'-(4-methylphenyl)sulfonyl-N-(2,3,5,6-tetrachloro-4-oxocyclohexa-2,5-dien-1-ylidene)benzenecarboximidamide
• CAS: 308292-17-3
• 化学式: C₂₀H₁₂Cl₄N₂O₃S
• 分子量: 502.205
• InChiKey: JBOUAASQLHBZDY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  84.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N'-(4-methylphenyl)sulfonyl-N-(2,3,5,6-tetrachloro-4-oxocyclohexa-2,5-dien-1-ylidene)benzenecarboximidamide 在 氯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以50%的产率得到N-(2,3,5,5,6,6-hexachloro-4-oxocyclohex-2-en-1-ylidene)-N'-(4-methylphenyl)sulfonylbenzenecarboximidamide
  参考文献：
  名称：

  摘要：

  The study of chlorination of N-(N-arylsulfonylarylimidoyl)-1,4-benzoquinone imines and of N-(N-arylsulfonylarylimidoyl)-1,4-aminophenols revealed that the dominant stage in the process was the formation of cyclohexene structures, 4-(N-arylsulfonylarylimidoyl)imino-2,5,6-trichloro-2-cyclohexene-1-ones, resulting from addition of a Cl-2 molecule across the C=C bond of the quinoid ring. These substances suffer a prototropic rearrangements yielding N-(N-arylsulfonylarylimidoyl)-2,3,6-trichloro-4-aminophenols. The latter are the most common reaction products. The products of deeper chlorination were also obtained.

  DOI：

  10.1023/a:1016555324390
• 作为产物：
  描述：

  N²-p-Toluolsulfonyl-N¹-(4'-hydroxyphenyl)benzamidin 在 氯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 N'-(4-methylphenyl)sulfonyl-N-(2,3,5,6-tetrachloro-4-oxocyclohexa-2,5-dien-1-ylidene)benzenecarboximidamide
  参考文献：
  名称：

  摘要：

  The study of chlorination of N-(N-arylsulfonylarylimidoyl)-1,4-benzoquinone imines and of N-(N-arylsulfonylarylimidoyl)-1,4-aminophenols revealed that the dominant stage in the process was the formation of cyclohexene structures, 4-(N-arylsulfonylarylimidoyl)imino-2,5,6-trichloro-2-cyclohexene-1-ones, resulting from addition of a Cl-2 molecule across the C=C bond of the quinoid ring. These substances suffer a prototropic rearrangements yielding N-(N-arylsulfonylarylimidoyl)-2,3,6-trichloro-4-aminophenols. The latter are the most common reaction products. The products of deeper chlorination were also obtained.

  DOI：

  10.1023/a:1016555324390

文献信息

• ——
  作者：A. P. Avdeenko、I. L. Marchenko、S. A. Konovalova

  DOI：10.1023/a:1012377401470

  日期：——

  The direction of hydrohalogenation of N-substituted p-quinonimines was predicted on the basis of orbital coefficients of the C-2 and C-3 atoms in the lowest unoccupied molecular orbital, calculated by the PM3 method. It was assumed that the reaction is orbital-controlled and that the initial act of hydrohalogenation is nucleophilic attack by halide ion. The proposed approach was verified by experimental hydrochlorination and hydrobromination of N-(N-arylsulfonylbenzimidoyl)-1,4-benzoquinonimines which take up HHlg molecule following the 1,4-addition scheme, i.e., the halogen atom adds to C-2 of the quinoid ring.