N-[(4-nitrophenyl)thio]-2,6-dichloro-1,4-benzoquinone imine | 5147-73-9

• 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-nitrophenyl)thio]-2,6-dichloro-1,4-benzoquinone imine
• 英文别名: N-(p-Nitrophenylsulfenyl)-2,6-dichlorchinonimin；2,6-Dichloro-4-(4-nitrophenyl)sulfanyliminocyclohexa-2,5-dien-1-one
• CAS: 5147-73-9
• 化学式: C₁₂H₆Cl₂N₂O₃S
• 分子量: 329.163
• InChiKey: KCYRBDUWFUKGCD-UHFFFAOYSA-N

物化性质

• 熔点：
  260-262 °C
• 沸点：
  474.3±55.0 °C(Predicted)
• 密度：
  1.57±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  101
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-硝基苯亚磺酰氯 、 2,6-二氯-4-氨基苯酚 在 三乙胺 、 碘苯二乙酸 作用下， 以 乙醚 、 溶剂黄146 为溶剂， 以30%的产率得到N-[(4-nitrophenyl)thio]-2,6-dichloro-1,4-benzoquinone imine
  参考文献：
  名称：

  Comparison of preparation methods of N-arylsulfinyl-1,4-benzoquinone monoimines

  摘要：

  讨论了三种制备N-芳基亚磺酰基-1,4-苯醌亚胺的工艺的优缺点：芳基硫酰氯与1,4-苯醌肟的反应、N-芳基硫-1,4-苯醌亚胺的氧化，以及芳基亚磺酰氯与对氨基酚的反应后氧化。获得了一系列新的N-芳基亚磺酰基-1,4-苯醌亚胺。

  DOI：

  10.1134/s1070428008020085

文献信息

• <i>Z</i>,<i>E</i>-Isomerization mechanism for<i>N</i>-arylthio-1,4-benzoquinonimines: DNMR and DFT investigations
  作者：V. V. Pirozhenko、A. B. Rozhenko、A. P. Avdeenko、S. A. Konovalova、A. A. Santalova

  DOI：10.1002/mrc.2254

  日期：2008.9

  Z, E‐Isomerization has been investigated for the series of the N‐arylthio‐1,4‐benzoquinonimines using a line shape analysis in the 1H NMR spectra. Thermodynamic parameters and substituent effects have been analyzed for the isomerization process. It has been shown based on the DFT (B3LYP) calculations that the dynamic transformation for N‐arylthio‐1,4‐benzoquinonimines should be considered as a combination

  已经使用 1H NMR 谱中的线形分析研究了 N-芳硫基-1,4-苯醌亚胺系列的 Z, E-异构化。分析了异构化过程的热力学参数和取代基效应。基于 DFT (B3LYP) 计算表明，N-芳硫基-1,4-苯醌亚胺的动态转化应被视为两种不同过程的组合，围绕 NS 键的旋转和在氮通过具有线性 C NS 部分的过渡态。实验测量的异构化活化的自由能 (ΔG298 K) 取决于醌亚胺部分和苯环中的取代，并且可以指氮原子的反转或围绕 NS 键的受阻旋转。版权所有 © 2008 John Wiley &
• ——
  作者：V. V. Pirozhenko、A. P. Avdeenko、A. L. Yusina、S. A. Konovalova

  DOI：10.1023/a:1020945308712

  日期：——

  Introduction of chlorine substituents into quinone imine fragment results in virtually the same variations in the chemical shifts of the quinoid ring carbons both in N-arylthio and N-arylsulfonyl-1,4-benzoquinone imines as compared to the unsubstituted analogs. In both classes of chloro-substituted compounds the effect of substituents in the benzene ring on the character and the range of chemical shifts variations for the carbon signals from the quinoid ring also turned out to be identical. Any differences observed may be due to the change in the geometry of the molecules, in particular, to the increase in the bond angle C=N-S.
• Reactions of arylsulfinyl chlorides and N-(arylsulfonyl)arylsulfinimidoyl chlorides with p-aminophenols
  作者：A. P. Avdeenko、S. A. Konovalova、A. A. Santalova

  DOI：10.1134/s1070428007100107

  日期：2007.10

  In reactions of arylsulfinyl chlorides and N-(arylsulfonyl)arylsulfinimidoyl chlorides with p-aminophenols formed N-arylthio-1,4-benzoquinone imines, evidently through a stage of N- arylsulfinyl-4-aminophenols and N-(N- arylsulfonyl)arylsulfinylimidoyl-4-aminophenols that under the reaction conditions eliminate respectively H2O and ArSO2NH2.
• Comparison of preparation methods of N-arylsulfinyl-1,4-benzoquinone monoimines
  作者：A. P. Avdeenko、S. A. Konovalova、A. A. Santalova

  DOI：10.1134/s1070428008020085

  日期：2008.2

  Advantages and shortcomings were discussed of three procedures for preparation N-arylsulfinyl-1,4-benzoquinone imines: the reaction of arenesulfenyl chlorides with 1,4-benzoquinone oximes, the oxidation of N-arylthio-1,4-benzoquinone imines, and the reaction of arylsulfinyl chlorides with p-aminophenols followed by oxidation. A series of new N-arylsulfinyl-1,4-benzoquinone imines was obtained.

  讨论了三种制备N-芳基亚磺酰基-1,4-苯醌亚胺的工艺的优缺点：芳基硫酰氯与1,4-苯醌肟的反应、N-芳基硫-1,4-苯醌亚胺的氧化，以及芳基亚磺酰氯与对氨基酚的反应后氧化。获得了一系列新的N-芳基亚磺酰基-1,4-苯醌亚胺。