N-(3-bromo-4-hydroxyphenyl)-N'-(4-methylphenyl)sulfonylbenzenecarboximidamide | 308291-86-3

• 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-(3-bromo-4-hydroxyphenyl)-N'-(4-methylphenyl)sulfonylbenzenecarboximidamide
• CAS: 308291-86-3
• 化学式: C₂₀H₁₇BrN₂O₃S
• mdl: MFCD02079064
• 分子量: 445.337
• InChiKey: VQMQSNNQCSTJFK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  87.1
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(3-bromo-4-hydroxyphenyl)-N'-(4-methylphenyl)sulfonylbenzenecarboximidamide 在 lead(IV) acetate 、 氢溴酸 作用下， 以 溶剂黄146 为溶剂， 生成 N-(3,5-dibromo-4-hydroxyphenyl)-N'-(4-methylphenyl)sulfonylbenzenecarboximidamide
  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'-(4-methylphenyl)sulfonyl-N-(4-oxocyclohexa-2,5-dien-1-ylidene)benzenecarboximidamide 在 氢溴酸 作用下， 以 溶剂黄146 为溶剂， 以65%的产率得到N-(3-bromo-4-hydroxyphenyl)-N'-(4-methylphenyl)sulfonylbenzenecarboximidamide
  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