3-(4-硝基苯基)-1,5-二(苯基)-1,2,4,5-四氮杂环己-2-烯 | 31994-78-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3-(4-硝基苯基)-1,5-二(苯基)-1,2,4,5-四氮杂环己-2-烯
• 英文名称: 3-(4-nitrophenyl)-1,5-diphenylverdazyl
• 英文别名: 2,4-diphenyl-6-(4-nitrophenyl)verdazyl；2,4-diphenyl-6-(4-nitrophenyl)-3,4-dihydro-1,2,4,5-tetrazin-1(2H)-yl
• CAS: 31994-78-2
• 化学式: C₂₀H₁₆N₅O₂
• 分子量: 358.379
• InChiKey: UKPWQAIIVKAFCL-UHFFFAOYSA-N

物化性质

• 熔点：
  205-206 °C(Solv: N,N-dimethylformamide (68-12-2); water (7732-18-5))

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  65.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(4-硝基苯基)-1,5-二(苯基)-1,2,4,5-四氮杂环己-2-烯 在 1,2-二苯肼 作用下， 以 苯 为溶剂， 生成 6-(4-硝基苯基)-2,4-二苯基-1,3-二氢-1,2,4,5-四嗪
  参考文献：
  名称：

  Polumbrik, O.M.; Ryabokon', I.G.; Markovskii, L.N., Journal of Organic Chemistry USSR (English Translation), 1982, vol. 18, p. 917 - 921

  摘要：

  DOI：
• 作为产物：
  描述：

  对硝基苯甲醛 在 盐酸 、 potassium hydrogensulfate 、 sodium acetate 、 sodium hydroxide 、 sodium nitrite 作用下， 以 1,4-二氧六环 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 45.0h， 生成 3-(4-硝基苯基)-1,5-二(苯基)-1,2,4,5-四氮杂环己-2-烯
  参考文献：
  名称：

  Triarylverdazyl 自由基作为可充电有机电池的有希望的氧化还原活性成分

  摘要：

  提出了一种基于带有各种取代基的稳定 Verdazyl 自由基的可充电有机电池电活性组件的新设计。verdazyl 部分的 3 位芳香取代基影响还原电位，几乎不影响氧化电位，而 1 位芳香取代基相反影响该自由基的氧化电位，而对还原电位没有任何影响。获得的电化学数据使我们能够揭示阴极和阳极过程的结构-电位关系，这提供了具有破纪录的“电化学间隙”参数的三芳基戊二烯自由基的设计。

  DOI：

  10.1007/s11172-020-2905-5
• 作为试剂：
  描述：

  3-溴环己烯 在 3-(4-硝基苯基)-1,5-二(苯基)-1,2,4,5-四氮杂环己-2-烯 、 高氯酸四乙基铵 作用下， 以 硝基苯 为溶剂， 生成 1,3-环己二烯
  参考文献：
  名称：

  摘要：

  The salt effect on the rate of dehydrobromination of 3-bromocyclohexene in PhNO2 depends on the nature of the verdazyl indicator, With triphenylverdazyl and its chloro and nitro derivatives in the presence of Et4NClO4, a normal salt effect is observed, in the presence of bromides, a superposition of normal and special salt effects, while in the presence of chlorides, a superposition of normal and special negative salt effects. With the dimethoxy verdazyl derivative, a normal salt effect is always observed.

  DOI：

  10.1023/a:1015349429876

文献信息

• Syntheses of 3-(substituted)-2,4,6-triphenylverdazyls
  作者：Alan R. Katritzky、Sergei A. Belyakov、H. Dupont Durst、Ruixin Xu、Naresh S. Dalal

  DOI：10.1139/v94-235

  日期：1994.8.1

  Two series of 2,4,6-triphenylverdazyls substituted at the C(3) position of the heterocyclic ring are obtained using new convenient synthetic methodology. Thus, crown ether assisted solid–liquid phase-transfer catalysis promotes the formation of 3-n-alkyl-substituted 2,4,6-triphenylverdazyls in the reactions of 1,3,5-triphenylformazan with n-alkyl bromides. Under PTC conditions, methylation of 3-(4-nitrophenyl)-1,5-diphenylformazan with methyl iodide exclusively gives the corresponding verdazyl radical. 3-Substituted 2,4,6-triphenylverdazyls containing various di(cyclo)alkylamino moieties at the C(3) position of the verdazyl ring are prepared by the reaction of 1,3,5-triphenylformazan with the corresponding 1-[N,N-di(cyclo)alkylaminomethyl]benzotriazoles under the efficient catalysis of barium hydroxide monohydrate. Sonication of this reaction allows the yields of the verdazyls to be substantially increased. A bis-verdazyl N,N-bonded in the C(3) positions was synthesized. All the radicals obtained were characterized by microanalysis, and by UV–visible and ESR spectroscopy.

  两系列在杂环环的C(3)位置取代的2,4,6-三苯基噻唑基物质，通过新的便捷合成方法得到。因此，冠醚辅助的固液相转移催化促进了1,3,5-三苯基咪唑基与n-烷基溴化物反应中3-n-烷基取代的2,4,6-三苯基噻唑基的形成。在PTC条件下，使用碘甲烷对3-(4-硝基苯基)-1,5-二苯基咪唑基进行甲基化，仅生成相应的噻唑基自由基。在噻唑基环的C(3)位置含有各种二(环)烷基氨基基团的3-取代的2,4,6-三苯基噻唑基通过1,3,5-三苯基咪唑基与相应的1-[N,N-二(环)烷基氨基甲基]苯并三唑在氢氧化钡单水合物的高效催化下反应制备。超声处理这个反应可以显著增加噻唑基的产率。合成了在C(3)位置N,N-键合的双噻唑基。所有获得的自由基都通过微量分析、UV-可见光谱和ESR光谱进行了表征。
• Synthesis and Electrochemical Properties of 2-(4-R1-Phenyl)-6-(4-R2-phenyl)-4-phenyl-3,4-dihydro1,2,4,5-tetrazin-1(2H)-yls
  作者：S. G. Kostryukov、A. V. Balandina、A. Sh. Kozlov、E. V. Kraynov、M. K. Pryanichnikova、O. Yu. Chernyaeva、A. A. Akhmatova、Yu. I. Lukshina

  DOI：10.1134/s1070363220030044

  日期：2020.3

  A new methodology for creating electroactive components for organic batteries, based on the construction of a molecular platform including stable 3,4-dihydro-1,2,4,5-tetrazin-1(2H)-yl radicals was described. A series of 2-(4-R-1-phenyl)-6-(4-R-2-phenyl)-4-phenyl-3,4-dihydro-1,2,4,5-tetrazin-1(2H)-yls with substituents of various nature was obtained. It was shown that the substituents R-1 in the aromatic ring at position 2 of the tetrazinyl fragment influence the value of the oxidation potential in the radical, but do not influence the value of the reduction potentials, while the substituent R-2 of the aromatic ring at position 6 influence the values of the reduction potentials and practically do not influence oxidation potential values. Based on the obtained electrochemical data, a correlation structure-potential value was revealed for the cathodic and anodic process, with the help of which triarylsubstituted 3,4-dihydro-1,2,4,5-tetrazin-1(2H)-yl radicals with high values of the electrochemical gap were obtained.
• Ponomareva, E. A.; Tarasenko, P. V.; Yurchenko, A. G., Journal of Organic Chemistry USSR (English Translation), 1983, vol. 19, p. 481 - 493
  作者：Ponomareva, E. A.、Tarasenko, P. V.、Yurchenko, A. G.、Dvorko, G. F.

  DOI：——

  日期：——
• Polumbrik, O.M.; Ryabokon', I.G.; Skorobagat'ko, E.P., Journal of Organic Chemistry USSR (English Translation), 1982, vol. 18, p. 922 - 927
  作者：Polumbrik, O.M.、Ryabokon', I.G.、Skorobagat'ko, E.P.、Nesterenko, A.M.、Markovskii, L.N.

  DOI：——

  日期：——
• Adiabatic and nonadiabatic transition events in the reaction of verdazyl radicals with mercuric chloride
  作者：L. S. Degtyarev、A. A. Stetsenko

  DOI：10.1007/bf00518087

  日期：——