N-{[(benzenesulfonyl)-imino](phenyl)methyl}-3,5-dimethyl-1,4-benzoquinone imine | 308291-68-1

• 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-{[(benzenesulfonyl)-imino](phenyl)methyl}-3,5-dimethyl-1,4-benzoquinone imine
• 英文别名: N'-(benzenesulfonyl)-N-(3,5-dimethyl-4-oxocyclohexa-2,5-dien-1-ylidene)benzenecarboximidamide
• CAS: 308291-68-1
• 化学式: C₂₁H₁₈N₂O₃S
• 分子量: 378.452
• InChiKey: RUAFNDYYSNQGJI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 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-{[(benzenesulfonyl)-imino](phenyl)methyl}-3,5-dimethyl-1,4-benzoquinone imine 在 盐酸 作用下， 以 氯仿 为溶剂， 反应 0.5h， 以68%的产率得到N-[1-(2-Chloro-4-hydroxy-3,5-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
• 作为产物：
  描述：

  N-(氯苯基亚甲基)-苯磺酰胺 在 lead(IV) acetate 、 sodium acetate 作用下， 以 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 N-{[(benzenesulfonyl)-imino](phenyl)methyl}-3,5-dimethyl-1,4-benzoquinone imine
  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