2,5-dipyrazol-1-yl-1,4-benzoquinone | 39736-44-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,5-dipyrazol-1-yl-1,4-benzoquinone
• 英文别名: 2,5-di(1H-pyrazol-1-yl)-1,4-benzoquinone；2,5-(pyrazol-1-yl)benzoquinone；2,5-Di(pyrazol-1-yl)cyclohexa-2,5-diene-1,4-dione
• CAS: 39736-44-2
• 化学式: C₁₂H₈N₄O₂
• 分子量: 240.221
• InChiKey: UGKZGUXROYIUQY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 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：
  69.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [ruthenium(II)(hydride)(chloride)(carbonyl)(triphenylarsine)3] 、 2,5-dipyrazol-1-yl-1,4-benzoquinone 以 乙醇 为溶剂， 反应 3.0h， 以49%的产率得到
  参考文献：
  名称：

  螯合对含有2,5-二（1 H-吡唑-1-基）-1,4-苯醌的有机金属钌（ii）配合物抗癌活性的影响：合成，结构，DNA /蛋白质结合，抗氧化活性和细胞毒性†

  摘要：

  为了深入了解螯合剂对抗癌活性的影响，使用了两种新的二价有机金属钌络合物[Ru（L）Cl（CO）（PPh 3）2 ]（3）和[Ru（L）Cl（CO）（AsPh）3）2 ]（4）（HL = 2,5-二（1 H-吡唑-1-基）-1,4-苯醌），通过元素分析，IR，电子，1 H /已经研究了13 C NMR光谱研究及其生物学活性（DNA /蛋白质相互作用，抗氧化剂和细胞毒性活性研究），并将其与适当的前体复合物[RuHCl（CO）（PPh 3）3进行了比较。]（1），[RuHCl（CO）（AsPh 3）3 ]（2）和配体LH。新的配合物3和4的晶体结构均通过单晶X射线衍射研究确定，该研究揭示了中心钌离子采用扭曲的八面体几何结构，其中L作为一元二齿双键供体，并且观察到螯合剂经历了C–H在邻位之一激活导致形成五元金属环的位置。已通过光物理研究检查了复合物的DNA /蛋白质相互作用，这表明复合物与DNA的

  DOI：

  10.1039/c6ra05867a
• 作为产物：
  描述：

  2,5-bis(pyrazol-1'-yl)-1,4-dihydroxybenzene 在 对苯醌 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.0h， 以71%的产率得到2,5-dipyrazol-1-yl-1,4-benzoquinone
  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

• Reaction of pyrazole addition to quinones
  作者：Paloma Ballesteros、Rosa M. Claramunt、Consuelo Escolastico、M. Dolores Santa Maria、Jose Elguero

  DOI：10.1021/jo00032a048

  日期：1992.3

  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.
• Ding, Li; Biani, Fabrizia Fabrizi de; Bolte, Michael, Organometallics, 2000, vol. 19, p. 5763 - 5768
  作者：Ding, Li、Biani, Fabrizia Fabrizi de、Bolte, Michael、Zanello, Piero、Wagner Matthias

  DOI：——

  日期：——
• High-temperature metal-organic acceptor magnets
  申请人：Jain Rajsapan

  公开号：US20070164251A1

  公开（公告）日：2007-07-19

  A stable magnet having a high Tc is provided. The stable magnet is synthesized from an at least one ion of a metal from a metal-containing precursor and molecules of an organic compound in a metal to organic ratio of at least about 1 ion to 1 organic molecule and as much as 10 or more ions to 1 organic molecule. The metal-containing precursor provides at least one ion having a valency lower than its maximum valency state. The organic molecules are selected from a group of organic compounds having a reduction potential suitable to accept at least one electron from the metal ion and an at least one functional group that is able to coordinate with the metal ion.
• HIGH-TEMPERATURE METAL-ORGANIC ACCEPTOR MAGNETS
  申请人：Jain Rajsapan

  公开号：US20100267978A1

  公开（公告）日：2010-10-21

  A stable magnet having a high Tc is provided. The stable magnet is synthesized from an at least one ion of a metal from a metal-containing precursor and molecules of an organic compound in a metal to organic ratio of at least about 1 ion to 1 organic molecule and as much as 10 or more ions to 1 organic molecule. The metal-containing precursor provides at least one ion having a valency lower than its maximum valency state. The organic molecules are selected from a group of organic compounds having a reduction potential suitable to accept at least one electron from the metal ion and an at least one functional group that is able to coordinate with the metal ion.
• Redox Behaviour of Pyrazolyl-Substituted 1,4-Dihydroxyarenes: Formation of the Corresponding Semiquinones, Quinhydrones and Quinones
  作者：Hans-Wolfram Lerner、Günter Margraf、Tonia Kretz、Olav Schiemann、Jan W. Bats、Gerd Dürner、Fabrizia Fabrizi de Biani、Piero Zanello、Michael Boltea、Matthias Wagner

  DOI：10.1515/znb-2006-0304

  日期：2006.3.1

  Pyrazolyl-substituted 1,4-dihydroxybenzene and 1,4-dihydroxynaphthene derivatives have been synthesized by reaction of 1,4-benzoquinone and 1,4-naphthoquinone, respectively, with pyrazole. Cyclovoltammetric measurements have shown that 1,4-benzoquinone possesses the potential to oxidize 2-(pyrazol-1-yl)- and 2,5-bis(pyrazol-1-yl)-1,4-dihydroxybenzene. The 2,5-bis(pyrazol-1-yl)- 1,4-dihydroxybenzene reacts with air to give quantitatively black insoluble 2,5-bis(pyrazol-1-yl)-1,4- quinhydrone. Black crystals of 2,5-bis(pyrazol-1-yl)-1,4-quinhydrone suitable for X-ray diffraction were grown from methanol at ambient temperature (monoclinic C2/c). The poor yields of pyrazolylsubstituted 1,4-dihydroxybenzene and 1,4-dihydroxynaphthene derivatives can be explained by the formation of insoluble black quinhydrons in the reaction of benzoquinone and naphthoquinone with pyrazole. The dianions of 2-(pyrazol-1-yl)- and 2,5-bis(pyrazol-1-yl)-1,4-dihydroxybenzene react with oxygen to give the corresponding semiquinone anions. 2,5-Bis(pyrazol-1-yl)-1,4-benzoquinone shows two reversible one-electron reduction processes in cyclovoltammetric measurements, whereas pyrazolyl-substituted 1,4-dihdroxybenzene and -naphthene derivatives undergo irreversibile electrontransfer processes.

  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。