N-(3,5-dichloro-4-hydroxyphenyl)-N'-(phenylsulfonyl)benzenecarboximidamide | 314751-12-7

• 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-(3,5-dichloro-4-hydroxyphenyl)-N'-(phenylsulfonyl)benzenecarboximidamide
• 英文别名: N'-(benzenesulfonyl)-N-(3,5-dichloro-4-hydroxyphenyl)benzenecarboximidamide
• CAS: 314751-12-7；408346-36-1
• 化学式: C₁₉H₁₄Cl₂N₂O₃S
• 分子量: 421.304
• InChiKey: QZMXUJFKZPFVCV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 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-(3,5-dichloro-4-hydroxyphenyl)-N'-(phenylsulfonyl)benzenecarboximidamide 在 lead(IV) acetate 作用下， 以 溶剂黄146 为溶剂， 以75%的产率得到N'-(benzenesulfonyl)-N-(3,5-dichloro-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
• 作为产物：
  描述：

  N²-Benzolsulfonyl-N¹-(4'-hydroxyphenyl)benzamidin 在 氯 作用下， 以 溶剂黄146 为溶剂， 以63%的产率得到N-(3,5-dichloro-4-hydroxyphenyl)-N'-(phenylsulfonyl)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.