3-(4-nitrophenyl)-1,5-diphenylformazan | 56156-44-6

• 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: 3-(4-nitrophenyl)-1,5-diphenylformazan
• 英文别名: 3-(p-nitrophenyl)-1,5-diphenylformazan；1,5-diphenyl-3-p-nitrophenylformazan
• CAS: 56156-44-6
• 化学式: C₁₉H₁₅N₅O₂
• 分子量: 345.36
• InChiKey: DLARSDSEYVUIBT-YMGPPEANSA-N

物化性质

• 沸点：
  509.1±52.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.15
• 重原子数：
  26.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  92.25
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  3-(4-nitrophenyl)-1,5-diphenylformazan 在 1-氯苯并三氮唑 作用下， 以 苯 为溶剂， 反应 0.08h， 以95%的产率得到5-(4-nitro-phenyl)-2,3-diphenyl-tetrazolium; chloride
  参考文献：
  名称：

  Katritzky, Alan R.; Belyakov, Sergey A.; Lam, Jamshed N., Heterocycles, 1994, vol. 39, # 1, p. 73 - 80

  摘要：

  DOI：
• 作为产物：
  描述：

  (对硝基苯基)丙酮酸 、 苯胺 在 盐酸 、 sodium hydroxide 、 sodium nitrite 作用下， 生成 3-(4-nitrophenyl)-1,5-diphenylformazan
  参考文献：
  名称：

  丙酮酸衍生物的新合成大环冠-甲醛

  摘要：

  通过适当的双重氮盐4a-c与丙酮酸和芳基丙酮酸8a-c的偶氮偶联来制备大环冠-甲氮杂7a-c，12a-g。后者的容易获得的性质提供了对1，5-对称的双取代的3-芳基甲氮烷（例如10a-g）及其预期有价值的应用的大环冠衍生物的容易获得。

  DOI：

  10.1016/s0040-4020(01)89286-3

文献信息

• A Direct One-Step Preparation of Triarylverdazylium Salts from the Corresponding Triarylformazans
  作者：Alan R. Katritzky、Sergei A. Belyakov

  DOI：10.1055/s-1997-1516

  日期：1997.1

  6-(4-Substituted-phenyl)-2,4-diphenylverdazylium salts 2 (8 examples, 55-93%) were prepared by the reaction of 3-(4-substituted-phenyl)-1,5-diphenylformazans 1 with formaldehyde and different organic and inorganic acids in a two-phase chloroform/water medium by brief and gentle heating. Self-phase-transfer catalysis is apparently involved. Subsequent reductions of the salts 2 with excess ascorbic acid in the two-phase system give the corresponding verdazyl radicals, while in methanol the reduction proceeds to form leuco-verdazyls.

  6-(4-取代苯基)-2,4-二苯基verdazylium盐2（8个例子，产率55-93%）是通过将3-(4-取代苯基)-1,5-二苯基福尔马赞1与甲醛及不同有机和无机酸在双相氯仿/水介质中进行短暂温和加热反应制备的。显然涉及自相转移催化。随后在双相系统中用过量抗坏血酸还原盐2，生成相应的verdazyl自由基，而在甲醇中还原则形成亚甲基verdazyl。
• 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。
• Syntheses of Formazans Under Phase-Transfer Conditions
  作者：Alan A. Katritzky、Sergei A. Belyakov、Dai Cheng、H. Dupont Durst

  DOI：10.1055/s-1995-3958

  日期：1995.5

  Several 1,3,5-triarylformazans were synthesized (42-77%) using a new methodology. Azo-coupling of aryldiazonium salts with arylaldehyde arylhydrazones under mild basic conditions in two-phase liquid-liquid media is efficiently promoted by phase-transfer catalysts (onium salts or dicyclohexano-18-crown-6) at 5-25°C. The condensation of benzaldehyde with phenylhydrazine followed by phase-transfer catalyzed azo-coupling with phenyldiazonium chloride (one-pot procedure) gave 1,3,5-triphenylformazan in a 54% yield without isolation of the intermediate benzaldehyde phenylhydrazone. A double azo-coupling reaction of phenyldiazonium chloride with 9 different CH-active compounds afforded corresponding formazan only in the case of phenylpyruvic acid. Reaction in malonamide gave 3-carbamoyl-1,5-diphenylformazan instead of the expected 1,5-diphenylformazan.

  采用一种新方法合成了多种 1,3,5-三芳基甲臢（42-77%）。相转移催化剂（鎓盐或二环己烷-18-冠醚-6）可在 5-25°C 的温度下，在两相液液介质的温和碱性条件下有效促进芳基偶氮盐与芳基醛芳基肼的偶氮偶联反应。苯甲醛与苯肼发生缩合反应，然后在相转移催化下与苯基重氮氯化物发生偶氮偶联反应（一锅法），得到 1,3,5-三苯基甲酰肼，收率为 54%，且无需分离中间体苯甲醛苯腙。苯基重氮酰氯与 9 种不同的 CH 活性化合物进行双偶氮偶联反应，只有苯基丙酮酸能得到相应的甲臢。在丙二酰胺中反应得到的是 3-氨基甲酰基-1,5-二苯基甲臢，而不是预期的 1,5-二苯基甲臢。
• Belyakov, S. A., Journal of Organic Chemistry USSR (English Translation), 1989, vol. 25, # 10.2, p. 2034 - 2035
  作者：Belyakov, S. A.

  DOI：——

  日期：——
• Arylations mediated by lead(IV) in the presence of formazan and imine ligands
  作者：Amjid Iqbal、Mark G. Moloney、Hamid Latif Siddiqui、Amber L. Thompson

  DOI：10.1016/j.tetlet.2009.05.086

  日期：2009.8

  The use of formazan and imine ligands in arylations of beta-dicarbonyl systems by phenyl boronic acid/lead(IV) carboxylates is examined. (C) 2009 Elsevier Ltd. All rights reserved.