N'-(4-methylphenyl)sulfonyl-N-(4-oxocyclohexa-2,5-dien-1-ylidene)benzenecarboximidamide | 494210-56-9

• 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'-(4-methylphenyl)sulfonyl-N-(4-oxocyclohexa-2,5-dien-1-ylidene)benzenecarboximidamide
• CAS: 494210-56-9
• 化学式: C₂₀H₁₆N₂O₃S
• 分子量: 364.425
• InChiKey: ALGDHZCKMQKCTK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 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'-(4-methylphenyl)sulfonyl-N-(4-oxocyclohexa-2,5-dien-1-ylidene)benzenecarboximidamide 在 氯 作用下， 以 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 以79%的产率得到N'-(4-methylphenyl)sulfonyl-N-(2,3,5-trichloro-4-hydroxyphenyl)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
• 作为产物：
  描述：

  N-(氯苯基亚甲基)-4-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'-(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

文献信息

• Reaction of some N-substituted 1,4-benzoquinone imines with sodium arenesulfinates
  作者：S. A. Konovalova、A. P. Avdeenko、I. L. Marchenko

  DOI：10.1134/s1070428014070082

  日期：2014.7

  N-Arylsulfonyl, N-aroyl, and N-[arylsulfonylimino(phenyl)methyl] derivatives of 1,4-benzoquinone imine reacted with sodium arenesulfinates to give 1,4-, 1,6-, and 6,1-addition products which were formed according to two concurrent paths: direct nucleophilic addition of arenesulfinate anion to neutral quinone imine molecule and radical ion addition of arenesulfinate radical to radical anion derived

  Ñ -Arylsulfonyl，Ñ芳酰基，和Ñ - [arylsulfonylimino（苯基）甲基] -1,4-苯醌亚胺衍生物与钠arenesulfinates反应，得到1,4-，1,6-，和6,1加成产物，其根据两个并发路径形成：将芳族亚磺酸根阴离子直接亲核加成到中性醌亚胺分子上，以及将芳族亚磺酸根自由基加成至醌基亚胺衍生的自由基上的自由基离子。
• ——
  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.
• ——
  作者：A. P. Avdeenko、V. V. Pirozhenko、L. M. Yagupol'skii、I. L. Marchenko

  DOI：10.1023/a:1012430601142

  日期：——

  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.
• ——
  作者：A. P. Avdeenko、I. L. Marchenko、S. A. Konovalova

  DOI：10.1023/a:1016555324390

  日期：——

  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.