2,3,5,6-tetrachlorohydroquinone diacetate | 5533-10-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: 2,3,5,6-tetrachlorohydroquinone diacetate
• 英文别名: 1,4-diacetoxy-2,3,5,6-tetrachloro-benzene；(Tetrachlor-p-phenylen)-diacetat；1,4-Diacetoxy-2,3,5,6-tetrachlor-benzol；Tetrachlorhydrochinon-diacetat；1,4-Benzenediol, 2,3,5,6-tetrachloro-, diacetate；(4-acetyloxy-2,3,5,6-tetrachlorophenyl) acetate
• CAS: 5533-10-8
• 化学式: C₁₀H₆Cl₄O₄
• 分子量: 331.967
• InChiKey: MGVDBRWFYNBCMA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,3,5,6-tetrachlorohydroquinone diacetate 在 sodium hydrogen sulfate 、 copper(II) sulfate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 4.0h， 以75%的产率得到
  参考文献：
  名称：

  [EN] HIGH-AND LOW-POTENTIAL, WATER-SOLUBLE, ROBUST QUINONES
  [FR] QUINONES ROBUSTES SOLUBLES DANS L'EAU À POTENTIEL FAIBLE ET ÉLEVÉ

  摘要：

  本文披露了取代的对苯二酚、1,4-喹啉醌、邻苯二酚、1,2-喹啉醌、蒽醌和蒽氢醌。取代的对苯二酚和邻苯二酚的化学式为：而取代的1,4-喹啉醌或1,2-喹啉醌具有相应的氧化结构（1,4-苯醌和1,2-苯醌）。R1、R2、R3和R4中的一个或多个包括磺酸酯基、磺酰胺基或膦酸酯基，而不包括这些基团之一的R1、R2、R3和R4包括烷基、环烷基、硫醚、亚硫醚、砜、卤代烷基、卤素、腈、酰亚胺、吡唑或其组合。取代的蒽醌的化学式为：而取代的蒽氢醌具有相应的还原结构。R1-R8中的一个或多个通过硫醚、胺或醚与环相连，包括一个或多个烷基。不含这些基团之一的R1-R8包括烷基、环烷基、硫醚、亚硫醚、砜、卤代烷基、卤素、羟基、烷氧基、醚、胺或氢的任何基团。取代的对苯二酚、1,4-喹啉醌、邻苯二酚、1,2-喹啉醌、蒽醌或蒽氢醌在水中溶解，在水酸性溶液中稳定，并且在氧化形式中具有有用的还原电位。因此，它们可以用作新兴技术中的氧化还原中介体，例如在介导燃料电池或有机介质流动电池中。

  公开号：

  WO2018160618A1
• 作为产物：
  描述：

  1,2,4,5-四氯-3-甲氧基-6-硝基苯 在 sodium dithionite 、 亚硝基硫酸 、 乙醇 、 硫酸 作用下， 生成 2,3,5,6-tetrachlorohydroquinone diacetate
  参考文献：
  名称：

  58. 1：2：4：5-四氯苯的衍生物。第一部分：硝基和氨基化合物

  摘要：

  DOI：

  10.1039/jr9430000233

文献信息

• Reactions of<i>p</i>-Benzoquinone Derivatives with Ethylenediamine
  作者：Teruzo Asahara、Manabu Sen\={o}、Takuma Teshirogi

  DOI：10.1246/bcsj.44.1687

  日期：1971.6

  reaction results of p-benzoquinone derivatives with various amino compounds, it becomes clear that chloranil reacts with ethylenediamine to afford an unexpected product. The spectroscopic analyses of the product show that this is an addition compound with some contribution of charge-transfer structures. Bromanil gives a similar product upon reaction with ethylenediamine.

  从对苯醌衍生物与各种氨基化合物的反应结果可以看出，氯苯醌与乙二胺反应得到了意想不到的产物。产物的光谱分析表明这是一种具有电荷转移结构的加成化合物。Bromanil 与乙二胺反应得到类似的产物。
• High-solubility thioether quinones
  申请人：Wisconsin Alumni Research Foundation

  公开号：US10597359B2

  公开（公告）日：2020-03-24

  Substituted hydroquinones and quinones and methods of synthesizing such compounds are disclosed herein. The substituted hydroquinones have the formula: while the substituted quinones have the corresponding oxidized structure (1,4-benzoquinones). One, two, three, or all four of R1, R2, R3 and R4 comprise a thioether moiety and a sulfonate moiety, and wherein each R1, R2, R3 and R4 that does not comprise a thioether and a sulfonate moiety sulfonate moiety is independently a hydrogen, an alkyl or an electron withdrawing group. The substituted hydroquinones and quinones are soluble in water, stable in aqueous acid solutions, and have a high reduction potential in the oxidized form. Accordingly, they can be used as redox mediators in emerging technologies, such as in mediated fuel cells or organic-mediator flow batteries.

  本文公开了取代的氢醌和醌类化合物以及合成此类化合物的方法。取代的对苯二酚具有以下式子 而取代的醌类具有相应的氧化结构（1,4-苯醌）。R1、R2、R3 和 R4 中的一、二、三或全部四个包含硫醚分子和磺酸分子，其中不包含硫醚分子和磺酸分子的每个 R1、R2、R3 和 R4 独立地是氢、烷基或取电子基团。取代的对苯二酚和醌类可溶于水，在酸性水溶液中稳定，在氧化形式下具有较高的还原电位。因此，它们可用作新兴技术中的氧化还原介质，如介导燃料电池或有机介质液流电池。
• High solubility thioether quinones
  申请人：Wisconsin Alumni Research Foundation

  公开号：US11021441B2

  公开（公告）日：2021-06-01

  Substituted hydroquinones and quinones and methods of synthesizing such compounds are disclosed herein. The substituted hydroquinones have the formula: while the substituted quinones have the corresponding oxidized structure (1,4-benzoquinones). One, two, three, or all four of R1, R2, R3 and R4 comprise a thioether moiety and a sulfonate moiety, and wherein each R1, R2, R3 and R4 that does not comprise a thioether and a sulfonate moiety sulfonate moiety is independently a hydrogen, an alkyl or an electron withdrawing group. The substituted hydroquinones and quinones are soluble in water, stable in aqueous acid solutions, and have a high reduction potential in the oxidized form. Accordingly, they can be used as redox mediators in emerging technologies, such as in mediated fuel cells or organic-mediator flow batteries.

  本文公开了取代的氢醌和醌类化合物以及合成此类化合物的方法。取代的对苯二酚具有以下式子 而取代的醌类具有相应的氧化结构（1,4-苯醌）。R1、R2、R3 和 R4 中的一、二、三或全部四个包含硫醚分子和磺酸分子，其中每个不包含硫醚分子和磺酸分子的 R1、R2、R3 和 R4 独立地是氢、烷基或取电子基团。 取代的对苯二酚和醌类可溶于水，在酸性水溶液中稳定，在氧化形式下具有较高的还原电位。因此，它们可用作新兴技术中的氧化还原介质，如介导燃料电池或有机介质液流电池。
• Acid Catalysis vs. Electron-Transfer Catalysis via Organic Cations or Cation-Radicals as the Reactive Intermediate. Are These Distinctive Mechanisms?
  作者：Rajendra Rathore、Jay K. Kochi、Augusto Canavesi、Larry L. Miller、Giovanni V. Sebastiani、George W. Francis、József Szúnyog、Bengt Långström

  DOI：10.3891/acta.chem.scand.52-0114

  日期：——

  Proton transfer to aromatic and olefinic donors (D) lends to the facile interchange of transient carbocations (DH+) and cation-radical (D+.). The same types of cation and cation-radical are reactive intermediates in the acid catalysis and the electron-transfer catalysis of such organic transformations as benzylic coupling, epoxide.-pinacol rearrangements and cis-trans isomerization of stilbenes when they are both carried out under otherwise identical reaction conditions, However, the rapid exchange of diamagnetic cations and paramagnetic cation-radicals blurs the traditional view of sepal ate electrophilic and homolytic processes, and rigorous experimental evidence is required to establish whether acid catalysis and electron-transfer catalysis actually represent distinct mechanistic categories.
• Properties of chlorinated dihydroxybenzenes — Components of pulp bleaching effluents
  作者：Terrence J. Smith、Ross H. Wearne、Adrian F.A. Wallis

  DOI：10.1016/0045-6535(94)90285-2

  日期：1994.10

  Gas chromatography and mass spectrometry data are given for the acetates of the chlorodihydroxybenzenes which are components of wood pulp bleaching effluents and biologically-treated effluents, and are proposed intermediates in the chlorination of humic acids. The chlorohydroxybenzenes include the nine chlorocatechols, the six chlorohydroquinones and the seven known chlororesorcinols. The 22 chlorinated compounds were generally well separated on a phenyl methyl silicone column with the exception of three dichloro compounds. The chloro compounds with the same level of chlorine substitution were not able to be distinguished on the basis of their electron impact mass spectra.