1,4-dihydroxy-2,3-bis(pyrazol-1'-yl)benzene | 123834-58-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1,4-dihydroxy-2,3-bis(pyrazol-1'-yl)benzene
• 英文别名: 2,3-bis(pyrazol-1'-yl)-1,4-dihydroxybenzene；1,4-dihydroxy-2,3-bis(pyrazol-1-yl)benzene；2,3-bis(pyrazol-1-yl)-1,4-dihydroxybenzene；2,3-Di(1H-pyrazol-1-yl)-1,4-benzenediol；2,3-di(pyrazol-1-yl)benzene-1,4-diol
• CAS: 123834-58-2
• 化学式: C₁₂H₁₀N₄O₂
• 分子量: 242.237
• InChiKey: LPZCYKKJSCUPHC-UHFFFAOYSA-N

物化性质

• 沸点：
  486.7±45.0 °C(Predicted)
• 密度：
  1.46±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  76.1
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,4-dihydroxy-2,3-bis(pyrazol-1'-yl)benzene 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 1,4-二氧六环 为溶剂， 反应 25.0h， 生成 tetrapyrazolylhydroquinone
  参考文献：
  名称：

  Reaction of pyrazole addition to quinones

  摘要：

  The reactions of pyrazole, 4-nitropyrazole, 3,5-dimethylpyrazole, and 4-chloro-3,5-dimethylpyrazole with 1,4-benzoquinone in dioxane have been analyzed. Mono- and 2,3-bis-adducts were obtained and only in the case of pyrazole was a 2,5-bis(pyrazol-1-yl)-1,4-dihydroxybenzene formed. Further oxidation of the mono- and bis-adducts with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) afforded the quinones, which in turn added 1 mol of azole (pyrazole and imidazole) to yield tetrapyrazolylquinols. Nitration of the 2,3-bis(pyrazol-1-yl)- and 2,3-bis(3,5-dimethylpyrazol-1-yl)-1,4-dihydroxybenzenes has been performed to prepare the corresponding 4-nitropyrazolyl derivatives.

  DOI：

  10.1021/jo00032a048
• 作为产物：
  描述：

  吡唑 、 对苯醌 以 1,4-二氧六环 为溶剂， 反应 1.0h， 以30%的产率得到2,5-bis(pyrazol-1'-yl)-1,4-dihydroxybenzene
  参考文献：
  名称：

  Redox Behaviour of Pyrazolyl-Substituted 1,4-Dihydroxyarenes: Formation of the Corresponding Semiquinones, Quinhydrones and Quinones

  摘要：

  摘要：通过1,4-苯醌和1,4-萘醌与吡唑反应，合成了吡唑基取代的1,4-二羟基苯和1,4-二羟基萘衍生物。循环伏安测量表明，1,4-苯醌具有氧化2-(吡唑-1-基)-和2,5-双(吡唑-1-基)-1,4-二羟基苯的潜力。2,5-双(吡唑-1-基)-1,4-二羟基苯与空气反应，定量生成不溶于黑色2,5-双(吡唑-1-基)-1,4-喹喙醌。适用于X射线衍射的黑色2,5-双(吡唑-1-基)-1,4-喹喙醌晶体从甲醇在室温下生长（单斜C2/c）。解释了吡唑基取代的1,4-二羟基苯和1,4-二羟基萘衍生物的产率低，是由于苯醌和萘醌与吡唑反应形成不溶的黑色喹喙醌。2-(吡唑-1-基)-和2,5-双(吡唑-1-基)-1,4-二羟基苯的二阴离子与氧反应生成相应的半喹喙醌负离子。2,5-双(吡唑-1-基)-1,4-苯醌在循环伏安测量中显示出两个可逆的单电子还原过程，而吡唑基取代的1,4-二羟基苯和-萘衍生物经历不可逆的电子转移过程。

  DOI：

  10.1515/znb-2006-0304

文献信息

• [EN] HIGH-AND LOW-POTENTIAL, WATER-SOLUBLE, ROBUST QUINONES<br/>[FR] QUINONES ROBUSTES SOLUBLES DANS L'EAU À POTENTIEL FAIBLE ET ÉLEVÉ
  申请人：WISCONSIN ALUMNI RES FOUND

  公开号：WO2018160618A1

  公开（公告）日：2018-09-07

  Substituted hydroquinones, 1,4-quinones, catechols, 1,2-quinones, anthraquinones, and anthrahydroquinones are disclosed herein. The substituted hydroquinones and catechols have the formula: while the substituted 1,4-quinones or 1,2-have the corresponding oxidized structure (1,4- benzoquinones and 1,2-benzoquinones). One or more of R1, R2, R3 and R4 include a sulfonate moiety, a sulfonimide moiety, or a phosphonate moiety, and any of R1, R2, R3 and R4 that do not include one of these moieties include an alkyl, a cycloalkyl, a thioether, a sulfoxide, a sulfone, a haloalkyl, a halogen, a nitrile, an imide, a pyrazole, or combinations thereof. The substituted anthraquinones have the formula: while the substituted anthrahydroquinones have the corresponding reduced structure. One or more of R1-R8 have a sulfonate or phosphate tethered to the ring by a thi other, amine, or ether including one or more alkyl groups. Any of R1-R8 that do not contain one of these moieties include an alkyl, a cycloalkyl, a thiother, a sulfoxide, a sulfone, a haloalkyl, a halogen, a hydroxyl, an alkoxyl, an ether, an amine, or hydrogen The substituted hydroquinones, 1,4-quinones, catechols, 1,2-quinones, anthraquinones, or anthrahydroquinones are soluble in water, stable in aqueous acid solutions, and have useful reduction potentials 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。
• Electronic properties of hydroquinone-containing ruthenium complexes in different oxidation states
  作者：Tia E. Keyes、Pradeep M. Jayaweera、John J. McGarvey、Johannes G. Vos

  DOI：10.1039/a607941e

  日期：——

  Some novel bis(2,2′-bipyridyl)ruthenium(II) complexes based on the ligands 1,4-dihydroxy-2,5-bis(pyrazol-1-yl)benzene (H 2 L p ) and 1,4-dihydroxy-2,3-bis(pyrazol-1-yl)benzene (H 2 L o ) have been prepared and characterized. The spectroscopic properties of the analogous H 2 L p complex containing deuteriated 2,2′-bipyridyl were also studied. The compounds have been oxidized and the electronic properties associated with both oxidation states examined in detail using resonance-Raman and UV/VIS/NIR spectroscopy. In the parent compounds the first redox process is hydroquinone based and the lowest-energy absorption is assigned to a hydroquinone to 2,2′-bipyridyl interligand transition. The products obtained upon oxidation are best described as ruthenium(II)–quinone complexes and their lowest-energy transition is assigned to a Ru II to quinone charge transfer.

  基于配体1,4-二羟基-2,5-双(吡唑-1-基)苯（H2Lp）和1,4-二羟基-2,3-双(吡唑-1-基)苯（H2Lo）的二（2,2′-联吡啶）钌（II）新式化合物（H2Lp和H2Lo）已经制备并表征。类似H2Lp（含氘代2,2′-联吡啶）的光谱性质也进行了研究。这些化合物已经氧化，并且使用共振拉曼和紫外/可见/近红外光谱详细研究了与两种氧化态相关的电子性质。在母体化合物中，第一个氧化还原过程是基于对苯二酚的，并且最低能量吸收被分配给对苯二酚到2,2′-联吡啶的过渡。氧化后得到的产品最好描述为钌（II）-醌的复合物，其最低能量转移被分配给Ru（II）到醌的电荷转移。
• Complexes of rhodium and iridium derived from 2,5-bis(pyrazol-1′-yl)-1,4-dihydroxybenzene
  作者：P. Cornago、C. Escolástico、M.D. Santa María、R.M. Claramunt、D. Carmona、M. Esteban、L.A. Oro、C. Foces-Foces、A.L. Llamas-Saiz、J. Elguero

  DOI：10.1016/0022-328x(94)80015-4

  日期：1994.3

  behaviour of the ligand 2,5-bis(pyrazol-1′-yl)-1,4-dihydroxybenzene (H2LL) towards RhI, IrI, RhIII and IrIII complexes is reported. This compound with two OH groups might act as a neutral ligand (H2LL), as a monoanionic ligand (HLL−) or as a dianionic ligand (LL2−). Complexes of all the three kinds have been isolated. In the case of H2LL, the compounds are not organometallic complexes but clathrates

  据报道，配体2，5-双（吡唑-1'-基）-1，4-二羟基苯（H 2 LL）对Rh I，Ir I，Rh III和Ir III配合物的行为。这具有两个OH基的化合物可能作为中性配体（H 2 LL），作为单阴离子配体（HLL -作为双阴离子配体（LL或）2- ）。三种复合物均已分离。在H 2 LL的情况下，化合物不是有机金属配合物，而是包合物。的主-客体复合物[晶体和分子结构（η 5 -C 5我5）的RhCl} 2 - （μ-Cl）的2报告了] -H 2 LL（6a）。宿主和客人都具有晶体学C i对称性。没有金属-H 2 LL化学键存在，主体分子和客体分子之间的范德华相互作用决定了晶体的堆积。一个的异衍生物[IrRh（η 5 -C 5我5）氯2（LL）]（图7c）已被分离。
• 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。
• Catalán, Javier; Fabero, Fernando; Soledad Guijarro, Journal of the American Chemical Society, 1990, vol. 112, # 2, p. 747 - 759
  作者：Catalán, Javier、Fabero, Fernando、Soledad Guijarro、Claramunt, Rosa M.、Dolores Santa María、De la Concepción Foces-Foces、Cano, Felix Hernández、Elguero, José、Sastre, Roberto

  DOI：——

  日期：——