6-(4-methoxyphenyl)-3-(2-pyridyl)-1,2,4-triazine 4-oxide | 517876-17-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 6-(4-methoxyphenyl)-3-(2-pyridyl)-1,2,4-triazine 4-oxide
• 英文别名: 6-(4-Methoxyphenyl)-4-oxido-3-pyridin-2-yl-1,2,4-triazin-4-ium
• CAS: 517876-17-4
• 化学式: C₁₅H₁₂N₄O₂
• 分子量: 280.286
• InChiKey: UVMKOZDRAQAMDG-UHFFFAOYSA-N

物化性质

• 沸点：
  550.3±60.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  73.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-(4-methoxyphenyl)-3-(2-pyridyl)-1,2,4-triazine 4-oxide 以 二氯甲烷 、 甲苯 为溶剂， 反应 2.03h， 生成 4-(4-methoxyphenyl)-1-(2-pyridyl)-6,7-dihydro-5H-cyclopenta[c]pyridine
  参考文献：
  名称：

  Luminescent neutral lanthanide complexes of 5-aryl-2,2′-bipyridine-6-carboxylic acids, synthesis and properties

  摘要：

  Luminescent lanthanide complexes of 4-aryl-1-(2-pyridyl)-6,7-dihydro-5H-cyclopenta[c]pyridine-3-carboxylic acids and 5-toly1-2,2'-bipyridine-6-carboxylic acid were prepared. The ligands were synthesized using the "1,2,4-triazine" methodology. In one case, the opportunity of copper complex preparation, followed by exchange of the metal cation from copper to europium to overcome synthetic difficulties, was demonstrated. The ability of tuning the properties of the complexes by means of varying the structure of the ligands was demonstrated. In particular, the introduction of the cyclopentene moiety allowed the preparation of highly soluble complexes in non-polar organic solvents. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2015.09.055
• 作为产物：
  描述：

  hydrazono-(4-methoxy-phenyl)-acetaldehyde oxime 在 lead(II,IV) oxide 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 生成 6-(4-methoxyphenyl)-3-(2-pyridyl)-1,2,4-triazine 4-oxide
  参考文献：
  名称：

  A Versatile Strategy for the Synthesis of Functionalized 2,2‘-Bi- and 2,2‘:6‘,2‘ ‘-Terpyridines via Their 1,2,4-Triazine Analogues

  摘要：

  A general synthetic route for the synthesis of functionalized bi- and terpyridines is reported. Functionalized 1,2,4-triazene 4-oxides 7 and 8-obtained from the reaction of hydrazones 1 with pyridine aldehydes and followed by oxidation-are functionalized by introduction of a cyano group via nucleophilic aromatic substitution. The thus-obtained 5-cyano-1,2,4-triazines 9 and 10 undergo facile inverse-electron-demand Diels-Alder reactions with enamines and alkenes to yield functionalized bi- and terpyridines, respectively. The substituent at position 6 of the 1,2,4-triazene 4-oxides must be aromatic or heteroaromatic in order to allow their facile synthesis, but other substituents and reagents may vary. Each step of the synthetic route allows diversification, which makes the approach particularly useful for the facile synthesis of a large variety of functionalized bi- and terpyridines.

  DOI：

  10.1021/jo0267955

文献信息

• 5-Acylmethyl-3-(2-pyridyl)-1,2,4-triazines: Synthesis and Complexes with Cu(II)
  作者：A. M. Prokhorov、D. N. Kozhevnikov、V. L. Rusinov、A. I. Matern、M. M. Nikitin、O. N. Chupakhin、I. L. Eremenko、G. G. Aleksandrov

  DOI：10.1007/s11178-006-0022-z

  日期：2005.11

  5-Acylmethyl-3-(2-pyridyl)-1,2,4-triazines are easily prepared from accessible 3-(2-pyridyl)-1,2,4-triazine 4-oxides by reaction of the latter with acetophenone or trifluoroacetone in the presence of NaH. The compounds obtained behaved as efficient ligands in reaction with CuCl2 furnishing dimeric neutral complexes with Cu(II) whose structure was investigated by means of X-ray diffraction analysis.

  5-乙酰甲基-3-(2-吡啶基)-1,2,4-三嗪类化合物通过可获得的3-(2-吡啶基)-1,2,4-三嗪4-氧化物与乙酰苯或三氟乙酰丙酮在NaH存在下的反应轻松制备。所得到的化合物作为高效配体与CuCl2反应，生成具有Cu(II)的二聚中性配合物，其结构通过X射线衍射分析进行了研究。
• An Efficient Cyanide-Free Approach towards 1-(2-Pyridyl)isoquinoline-3-carbonitriles via the Reaction of 5-Phenacyl-1,2,4-triazines with 1,2-Dehydrobenzene in the Presence of Alkyl Nitrites
  作者：Sougata Santra、Dmitry Kopchuk、Alexey Krinochkin、Albert Khasanov、Igor Kovalev、Pavel Slepukhin、Ekaterina Starnovskaya、Anindita Mukherjee、Matiur Rahman、Grigory Zyryanov、Adinath Majee、Vladimir Rusinov、Oleg Chupakhin

  DOI：10.1055/s-0036-1590961

  日期：2018.3

  -1,2,4-triazines with 1,2-dehydrobenzene generated in situ from anthranilic acid and an excess of amyl nitrites afforded the target compounds in good yields. The proposed mechanism involves the in situ transformation of the 5-phenacyl group into the 5-cyano group under the action of alkyl nitrite and the following inverse demand aza-Diels–Alder reaction of thus formed 5-cyano-1,2,4-triazines with 1

  开发了一种用于制备 1-(2-pyridyl)isoquinoline-3-carbonitriles (3-cyanoisoquinolines) 的无氰化物方法。5-phenacyl-3-(2-pyridyl)-1,2,4-triazines 与由邻氨基苯甲酸和过量亚硝酸戊酯原位生成的 1,2-脱氢苯相互作用，以良好的产率得到目标化合物。所提出的机制涉及在亚硝酸烷基酯的作用下 5-苯酰基基团原位转化为 5-氰基基团，以及由此形成的 5-氰基-1,2,4- 的逆向需求 aza-Diels-Alder 反应三嗪与 1,2-脱氢苯反应得到目标产物。5-苯甲酰基取代基的存在是反应的关键，如在 5-苯乙烯基-或 5-苯基乙炔基-3-(2-吡啶基)-1,2,4-三嗪的情况下，1,2观察到,4-三嗪环转化产物