N-[1-(3,5-Dibromo-4-hydroxy-2,6-dimethyl-phenylamino)-1-phenyl-meth-(Z)-ylidene]-benzenesulfonamide | 355856-97-2

• 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-[1-(3,5-Dibromo-4-hydroxy-2,6-dimethyl-phenylamino)-1-phenyl-meth-(Z)-ylidene]-benzenesulfonamide
• 英文别名: N'-(benzenesulfonyl)-N-(3,5-dibromo-4-hydroxy-2,6-dimethylphenyl)benzenecarboximidamide
• CAS: 355856-97-2
• 化学式: C₂₁H₁₈Br₂N₂O₃S
• 分子量: 538.26
• InChiKey: DRLKJPGXMSAPJH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.78
• 重原子数：
  29.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  78.76
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  N-[1-(3,5-Dibromo-4-hydroxy-2,6-dimethyl-phenylamino)-1-phenyl-meth-(Z)-ylidene]-benzenesulfonamide 在 lead(IV) acetate 作用下， 以 溶剂黄146 为溶剂， 以82%的产率得到N-[1-(3,5-Dibromo-2,6-dimethyl-4-oxo-cyclohexa-2,5-dienylideneamino)-1-phenyl-meth-(Z)-ylidene]-benzenesulfonamide
  参考文献：
  名称：

  摘要：

  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.

  DOI：

  10.1023/a:1012377401470
• 作为产物：
  描述：

  N-(2,6-dimethyl-4-oxocyclohexa-2,5-dienylidene)-N'-(phenylsulfonyl)benzimidamide 在 lead(IV) acetate 、 氢溴酸 作用下， 以 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.16h， 生成 N-[1-(3,5-Dibromo-4-hydroxy-2,6-dimethyl-phenylamino)-1-phenyl-meth-(Z)-ylidene]-benzenesulfonamide
  参考文献：
  名称：

  摘要：

  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.

  DOI：

  10.1023/a:1012377401470