4-chloro-N'-(4-methylphenyl)sulfonyl-N-(4-oxocyclohexa-2,5-dien-1-ylidene)benzenecarboximidamide | 355856-79-0

• 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: 4-chloro-N'-(4-methylphenyl)sulfonyl-N-(4-oxocyclohexa-2,5-dien-1-ylidene)benzenecarboximidamide
• CAS: 355856-79-0
• 化学式: C₂₀H₁₅ClN₂O₃S
• 分子量: 398.87
• InChiKey: FXAKHUSBYSFCAV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.92
• 重原子数：
  27.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  75.93
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  4-chloro-N'-(4-methylphenyl)sulfonyl-N-(4-oxocyclohexa-2,5-dien-1-ylidene)benzenecarboximidamide 在 lead(IV) acetate 、 盐酸 作用下， 以 氯仿 、 溶剂黄146 为溶剂， 反应 1.0h， 生成 N-[1-(4-Chloro-phenyl)-1-(3,5-dichloro-4-hydroxy-phenylamino)-meth-(Z)-ylidene]-4-methyl-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：

  4-chloro-N-(4-hydroxyphenyl)-N'-(4-methylphenyl)sulfonylbenzenecarboximidamide 在 lead(IV) acetate 作用下， 以 溶剂黄146 为溶剂， 以85%的产率得到4-chloro-N'-(4-methylphenyl)sulfonyl-N-(4-oxocyclohexa-2,5-dien-1-ylidene)benzenecarboximidamide
  参考文献：
  名称：

  摘要：

  Oxidation of N-(N-arylsulfonylimidoyl)-4-aminophenols gave the corresponding N-(N-arylsulfonylimidoyl)-1,4-benzoquinonimines, derivatives of N-aroyl- and N-acetyl-1,4-benzoquinonimines. The structure of the products was studied by the X-ray diffraction method and H-1 and C-13 NMR spectroscopy. N-(N-Arylsulfonylimidoyl)-1,4-benzoquinonimines were found to undergo fast (on the NMR time scale) Z,E isomerization about the C=N bond in the quinonimine fragment. N-(N-Arylsulfonylacetimidoyl)-1,4-benzoquinonimines in solution give rise to dynamic Z,E-isomerization with respect to the C=N bond in the N-arylsulfonylacetimidoyl fragment.

  DOI：

  10.1023/a:1012430601142