(4-methoxyphenyl)-(3-(4-methoxyphenyl)-1-phenyl-1H-1,2,4-triazol-5-yl)-ketone phenylhydrazone

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (4-methoxyphenyl)-(3-(4-methoxyphenyl)-1-phenyl-1H-1,2,4-triazol-5-yl)-ketone phenylhydrazone
• 英文别名: N-[[(4-methoxyphenyl)-[5-(4-methoxyphenyl)-2-phenyl-1,2,4-triazol-3-yl]methylidene]amino]aniline
• 化学式: C₂₉H₂₅N₅O₂
• 分子量: 475.55
• InChiKey: GAAHTRJBZGZYEC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.82
• 重原子数：
  36.0
• 可旋转键数：
  8.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  73.56
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  ethyl 3,8-bis-(4-methoxyphenyl)-1,6-diphenyl-1,5,6,8a-tetrahydro[1,2,4]triazolo[4,3-d][1,2,4]triazine-5-carboxylate 以 氯仿 为溶剂， 反应 12.0h， 以93%的产率得到(4-methoxyphenyl)-(3-(4-methoxyphenyl)-1-phenyl-1H-1,2,4-triazol-5-yl)-ketone phenylhydrazone
  参考文献：
  名称：

  The Behaviour of Nitrilimines Towards Ethyl Isocyanoacetate

  摘要：

  Interactions between nitrilimines and the title isocyanide afford, through two competing pathways, 2,3-diliydro-1,2,4-triazines and 1,3-oxazoles. In situ cycloaddition of unreacted nitrilimine with the triazines gives rise to a third class of products, the bicyclic 1,5,6,8a-tetrahydro[1,2,4]triazolo[4,3-d][1,2,4]triazines. Acceptor-free representatives of the latter are prone to triazine ring cleavage, yielding triazolyl ketone hydrazones which served as a structure proof. Substituent effects became apparent upon employment of N-(4-methoxyphenyl)- and N-(4-nitrophenyl)nitrilimines: whereas the former afforded a quinoxaline as the fourth product, triazine formation was totally blocked with the latter, the corresponding oxazole being the sole product. The constitution of acceptor-substituted bicyclic compounds (which failed to give the structure-revealing hydrazones) was established by an X-ray diffraction analysis.

  DOI：

  10.1007/s00706-002-0470-2

文献信息

• 1,2,3- and 1,2,4-triazolium salts, pyrazoles, and quinoxalines from diarylnitrilimines and isocyanides: A study of the scope
  作者：Dietrich Moderhack、Ali Daoud

  DOI：10.1002/jhet.5570400411

  日期：2003.7

  4-triazolium salts 11 are formed. Compounds 11 with tert-butyl group at the ring are unstable too, giving rise to triazoles 13. Pyrazole formation (analogues of 14) is completely suppressed when both tert-butyl and aryl isocyanides are used, whereas access to this ring system works best with see-alkyl isocyanides (the influence of substituents of 2 being almost negligible in this case). Formation of quinoxalines

  已经发现四种标题化合物的形成强烈地依赖于取代基：1,2,3-三唑鎓盐6并非由具有与C-或N-苯基连接的电子受体的腈2产生。同样，叔丁基和芳基异氰酸酯不提供这类化合物。由前者的异氰化物得到季铵化产物7，而由后者的1,2,4-三唑鎓盐11得到。在环上具有叔丁基的化合物11也不稳定，从而产生三唑13。吡唑的形成（类似14）当两个被完全抑制叔丁基和芳基异腈的使用，而访问该环系统的工作原理最好看到烷基异氰化物（的取代基的影响2是在这种情况下几乎可以忽略）。由中间体1，2-二重氮基22通过扩环形成喹喔啉23非常受雇于使用在N-苯基上带有供体取代基的2，并且在此前提下，闭环22实际上与性质无关异氰化物。的形成23不与观察到2 有受体基团。
• The Behaviour of Nitrilimines Towards Ethyl Isocyanoacetate
  作者：Dietrich Moderhack、Ali Daoud、Peter G. Jones

  DOI：10.1007/s00706-002-0470-2

  日期：2002.9.1

  Interactions between nitrilimines and the title isocyanide afford, through two competing pathways, 2,3-diliydro-1,2,4-triazines and 1,3-oxazoles. In situ cycloaddition of unreacted nitrilimine with the triazines gives rise to a third class of products, the bicyclic 1,5,6,8a-tetrahydro[1,2,4]triazolo[4,3-d][1,2,4]triazines. Acceptor-free representatives of the latter are prone to triazine ring cleavage, yielding triazolyl ketone hydrazones which served as a structure proof. Substituent effects became apparent upon employment of N-(4-methoxyphenyl)- and N-(4-nitrophenyl)nitrilimines: whereas the former afforded a quinoxaline as the fourth product, triazine formation was totally blocked with the latter, the corresponding oxazole being the sole product. The constitution of acceptor-substituted bicyclic compounds (which failed to give the structure-revealing hydrazones) was established by an X-ray diffraction analysis.