1,3,4,6-tetraphenyl-1,4-dihydro-1,2,4,5-tetrazine | 17355-78-1

• 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: 1,3,4,6-tetraphenyl-1,4-dihydro-1,2,4,5-tetrazine
• 英文别名: 1,4-dihydro-1,3,4,6-tetraphenyl-1,2,4,5-tetrazine；1,3,4,6-Tetraphenyl-1,4-dihydro-1,2,4,5-tetrazin；1,3,4,6-tetraphenyl-1,4-dihydro-[1,2,4,5]tetrazine；1,3,4,6-Tetraphenyl-1,4-dihydro-[1,2,4,5]tetrazin；1,3,4,6-Tetraphenyl-1,4-dihydro-symm.-tetrazin, 2,3,5,6-Tetraphenyl-2,5-dihydro-1,2,4,5-tetrazin；1,4-Dihydro-1,3,4,6-tetraphenyl-1,2,4,5-tetrazin；1,3,4,6-tetraphenyl-1,2,4,5-tetrazine
• CAS: 17355-78-1
• 化学式: C₂₆H₂₀N₄
• 分子量: 388.472
• InChiKey: UGHPWAQUZDYJGP-UHFFFAOYSA-N

物化性质

• 熔点：
  201-201.5 °C
• 沸点：
  527.5±33.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  31.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,3,4,6-tetraphenyl-1,4-dihydro-1,2,4,5-tetrazine 、 alkaline earth salt of/the/ methylsulfuric acid 生成 苯甲腈 、 苯胺
  参考文献：
  名称：

  Bamberger; Grob, Chemische Berichte, 1901, vol. 34, p. 523,526, 528, 529

  摘要：

  DOI：
• 作为产物：
  描述：

  α-chlorobenzaldehyde phenylhydrazone 在 ytterbium(III) triflate 、 对硝基苯甲腈 作用下， 以 氯苯 为溶剂， 生成 1,3,4,6-tetraphenyl-1,4-dihydro-1,2,4,5-tetrazine
  参考文献：
  名称：

  Novel Process for Synthesis of 1,2,4‐Triazoles: Ytterbium Triflate–Catalyzed Cyclization of Hydrazonyl Chlorides with Nitriles

  摘要：

  A series of 1,3,5-trisubstituted 1,2,4-triazoles were synthesized via the intermolecular cyclization of hydrazonyl chlorides with nitriles catalyzed by ytterbium triflate [Yb(OTf)(3)]. The amount of catalysis was discussed and Yb(OTf)(3) could be reused without loss of activity.

  DOI：

  10.1081/scc-200057976

文献信息

• The 1,3-Dipolar Cycloadditions of Nitrile Oxides and Nitrile Imines to Alkyl Dicyanoacetates
  作者：Richard Neidlein、Zhihua Sui

  DOI：10.1002/hlca.19910740306

  日期：1991.5.2

  with the 1,3-dipolar reagents arenecarbonitrile oxides 2′ and arenecarbonitrile imines 5′ to afford 1,2,4-oxadiazol and 1,2,4-triazol derivatives. The arenecarbonitrile oxides 2′ with electron-donating groups on the arene ring gave products 3a–d resulting from addition on both CN groups of 1, and those with electron-withdrawing groups provided mono-adducts 4a–e (Scheme 1). Arylnitrile imines 5′ reacted

  容易得到的烷基dicyanoacetates 1与1,3-偶极试剂反应arenecarbonitrile氧化物2 '和arenecarbonitrile亚胺5 '，得到1,2,4-恶二唑和1,2,4-三唑衍生物。在芳烃环上带有给电子基团的芳烃腈氧化物2 '产生的产物3a - d是在两个CN基团1上加成而得到的，而带有吸电子基团的芳烃腈提供了单加合物4a - e（方案1）。芳腈亚胺5 '与1反应生成双加和单加产物（方案2）; 双加合物8a，b具有酯结构，而单加合物6a - d具有乙烯酮-半缩醛结构。
• New Synthesis of 1-Substituted-1<i>H</i>-indazoles via 1,3-Dipolar Cycloaddition of <i>in situ</i> Generated Nitrile Imines and Benzyne
  作者：Christian Spiteri、Steve Keeling、John E. Moses

  DOI：10.1021/ol101150t

  日期：2010.8.6

  A new synthesis of 1-substitued-1H-indazoles via 1,3-dipolar cycloaddition of nitrile imines to benzyne is described. The reaction is completed within 5 min, affording the corresponding N(1)−C(3) disubstituted indazoles in moderate to excellent yields.

  描述了通过腈亚胺的1，3-偶极环加成反应生成苯并炔的1-取代-1 H-吲唑的新合成方法。反应在5分钟内完成，以中等至极好的收率得到相应的N（1）-C（3）二取代的吲唑。
• Nouvelle voie de synthese d'arylpyrazolo -[4,3-c]-quinoleines via la cycloaddition dipolaire −1,3
  作者：Boujemâa Daou、Mohamed Soufiaoui

  DOI：10.1016/s0040-4020(01)81014-0

  日期：1989.1

  inverse regiospecificity is observed comparatively to the one established for the N-methylindole and N-ethylindole. To establish that regiospecificity chemically, we synthetised furthers arylpyrazolo - [4,3-c] -quinolines by using the Friedländer condensation.

  已通过光谱和化学方法证明了二芳基亚硝胺（DANI）对杂环（如苯并呋喃和N-甲基吲哚）的区域特异性。与在吲哚核的2位具有烷氧基羰基官能团的N-烷基吲哚相比，对于N-甲基吲哚和N-乙基吲哚所确定的反向烷基特异性被观察到。为了通过化学方法确定该区域特异性，我们使用Friedländer缩合反应进一步合成了芳基吡唑并-[4,3-c]-喹啉。
• Synthesis of 1,2,4-Triazol-3-imines via Selective Stepwise Cycloaddition of Nitrile Imines with Organo-cyanamides
  作者：Pallavi Sharma、Shreesha V. Bhat、M. R. Ranga Prabhath、Andrew Molino、Elisa Nauha、David J. D. Wilson、John E. Moses

  DOI：10.1021/acs.orglett.8b01673

  日期：2018.7.20

  A convenient method for the synthesis of 1,2,4-triazol-3-imines through a selective, formal, 1,3-dipolar cycloaddition of organo-cyanamide ions with nitrile imine dipoles is reported. Hydrolysis of the 1,2,4-triazol-3-imines yields the corresponding 1,2,4-triazol-5-ones. A stepwise mechanism, supported by DFT calculations, is invoked to explain the reaction selectivity.

  报道了一种通过有机腈酰胺离子与腈亚胺偶极的选择性，形式，1,3-偶极环加成反应合成1,2,4-三唑-3-亚胺的简便方法。1,2,4-三唑-3-亚胺的水解产生相应的1,2,4-三唑-5-酮。调用DFT计算支持的逐步机制来解释反应的选择性。
• Clovis, James S.; Fliege, Werner; Huisgen, Rolf, Chemische Berichte, 1983, vol. 116, # 9, p. 3062 - 3070
  作者：Clovis, James S.、Fliege, Werner、Huisgen, Rolf

  DOI：——

  日期：——