N-(4-chlorophenylsulfonyl)-N'-(2,6-dimethyl-4-oxo-2,5-cyclohexadienylidene)benzamidine

• 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-chlorophenylsulfonyl)-N'-(2,6-dimethyl-4-oxo-2,5-cyclohexadienylidene)benzamidine
• 英文别名: N'-(4-chlorophenylsulfonyl)-N-(2,6-dimethyl-4-oxocyclohexa-2,5-dienylidene)benzimidamide；N'-(4-chlorophenylsulfonyl)-N-(2,6-dimethyl-4-oxocyclohexa-2,5-dien-1-ylidene)benzenecarboximidamide；N'-(4-chlorophenyl)sulfonyl-N-(2,6-dimethyl-4-oxocyclohexa-2,5-dien-1-ylidene)benzenecarboximidamide
• 化学式: C₂₁H₁₇ClN₂O₃S
• 分子量: 412.897
• InChiKey: ZYGQMMOVCBUSJM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  28
• 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-(4-chlorophenylsulfonyl)-N'-(2,6-dimethyl-4-oxo-2,5-cyclohexadienylidene)benzamidine 在 盐酸 、 lead(IV) tetraacetate 作用下， 以 氯仿 、 溶剂黄146 为溶剂， 反应 1.16h， 生成 N'-(4-chlorophenylsulfonyl)-N-(3,5-dichloro-2,6-dimethyl-4-oxocyclohexa-2,5-dien-1-ylidene)benzenecarboximidamide
  参考文献：
  名称：

  Hydrohalogenation of N-[arylsulfonylimino(phenyl)methyl]-1,4-benzoquinone monoimines having alkyl substituents in the quinoid ring

  摘要：

  Hydrohalogenation of N-[arylsulfonylimino(phenyl)methyl]-2,5(3,5)-dimethyl-1,4-benzoquinone monoimines follows exclusively the 1,4-addition pattern, whereas N-[arylsulfonylimino(phenyl)methyl]-2,6-dimethyl-1,4-benzoquinone monoimines take up hydrogen halides according to the 6,3-addition scheme.

  DOI：

  10.1134/s1070428011070116
• 作为产物：
  描述：

  N'-(4-chlorophenyl)sulfonyl-N-(4-hydroxy-2,6-dimethylphenyl)benzenecarboximidamide 在 lead(IV) tetraacetate 作用下， 以 溶剂黄146 为溶剂， 以82%的产率得到N-(4-chlorophenylsulfonyl)-N'-(2,6-dimethyl-4-oxo-2,5-cyclohexadienylidene)benzamidine
  参考文献：
  名称：

  Hydrohalogenation of N-[arylsulfonylimino(phenyl)methyl]-1,4-benzoquinone monoimines having alkyl substituents in the quinoid ring

  摘要：

  Hydrohalogenation of N-[arylsulfonylimino(phenyl)methyl]-2,5(3,5)-dimethyl-1,4-benzoquinone monoimines follows exclusively the 1,4-addition pattern, whereas N-[arylsulfonylimino(phenyl)methyl]-2,6-dimethyl-1,4-benzoquinone monoimines take up hydrogen halides according to the 6,3-addition scheme.

  DOI：

  10.1134/s1070428011070116

文献信息

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

  DOI：10.1023/a:1013860204257

  日期：——

  N-[N-Arylsulfonylbenz(acet)imidoyl]-3,5-dimethyl-1,4-benzoquinonimines react with alcohols to give the corresponding adducts at the activated C=N bond. The adducts lose alcohol molecule on heating to afford initial quinonimines. Hydrolysis of the title compounds leads to formation of the corresponding quinones and N-arylsulfonylamidines.
• Thiocyanation of N-arylsulfonyl-, N-aroyl-, and N-[(N-arylsulfonyl)benzimidoyl]-1,4-benzoquinone imines
  作者：A. P. Avdeenko、V. V. Pirozhenko、S. A. Konovalov、D. A. Roman’kov、G. V. Palamarchuk、O. V. Shishkinc

  DOI：10.1134/s1070428009030105

  日期：2009.3

  Reactions of thiocyanate ion with N-aroyl-, N-arylsulfonyl-, and N-(N-arylsulfonylbenzimidoyl)-1,4-benzoquinone imines follow the 1,4-addition pattern, and the adducts undergo intramolecular cyclization to give the corresponding N-substituted 5-amino-1,3-benzoxathiol-2-ones as final products.
• Reactions of N-substituted 2,6(3,5)-dialkyl-1,4-benzoquinone imines with arenesulfinic acids
  作者：A. P. Avdeenko、S. A. Konovalova、D. A. Roman’kov、K. S. Burmistrov、V. M. Nichvoloda、O. V. Shishkin、R. I. Zubatyuk、G. V. Palamarchuk

  DOI：10.1134/s1070428009010084

  日期：2009.1

  The regioselectivity in the reactions of N-arylsulfonyl-2,6-dialkyl-1,4-benzoquinone imines with arenesulfinic acids (1,6-, 6,1-, or 6,3-addition) is determined by steric factor, while in the reactions of N-aroyl-1,4-benzoquinone imines electronic effect of substituents in the quinoid ring is crucial. The reactions of N-arylsulfonyl-3,5-dimethyl-1,4-benzoquinone imines with arenesulfinic acids follow mainly the 1,4-addition pattern. N-(N-Arylsulfonylbenzimidoyl)-1,4-benzoquinone imines are capable of reacting in a way similar to both N-arylsulfonyl and N-aroyl derivatives.
• Hydrohalogenation of N-[arylsulfonylimino(phenyl)methyl]-1,4-benzoquinone monoimines having alkyl substituents in the quinoid ring
  作者：A. P. Avdeenko、S. A. Konovalova、V. V. Pirozhenko、O. P. Ledeneva、A. A. Santalova

  DOI：10.1134/s1070428011070116

  日期：2011.7

  Hydrohalogenation of N-[arylsulfonylimino(phenyl)methyl]-2,5(3,5)-dimethyl-1,4-benzoquinone monoimines follows exclusively the 1,4-addition pattern, whereas N-[arylsulfonylimino(phenyl)methyl]-2,6-dimethyl-1,4-benzoquinone monoimines take up hydrogen halides according to the 6,3-addition scheme.
• Halogenation of N′-(Arenesulfonyl)-N-[2,6(3,5)-dialkyl-4-oxocyclohexa-2,5-dien-1-ylidene]benzenecarboximidamides and Their Reduction Products
  作者：A. P. Avdeenko、S. A. Konovalova、S. V. Shishkina

  DOI：10.1134/s1070428021010061

  日期：2021.1