6-(4''-methoxyphenyl)-3-(2'-quinolyl)-1,2,4-triazine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 6-(4''-methoxyphenyl)-3-(2'-quinolyl)-1,2,4-triazine
• 英文别名: 2-[6-(4-Methoxyphenyl)-1,2,4-triazin-3-yl]quinoline；2-[6-(4-methoxyphenyl)-1,2,4-triazin-3-yl]quinoline
• 化学式: C₁₉H₁₄N₄O
• 分子量: 314.346
• InChiKey: VPBWFYRAVZRNJJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  24
• 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：
  60.8
• 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'-quinolyl)-1,2,4-triazine 在 正丁基锂 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 正己烷 、 乙酸乙酯 为溶剂， 反应 2.17h， 生成 2-(6-(4-methoxyphenyl)-5-(perfluorophenyl)-1,2,4-triazin-3-yl)quinoline
  参考文献：
  名称：

  Direct C H/C Li coupling of 1,2,4-triazines with C6F5Li followed by aza-Diels-Alder reaction as a pot, atom, and step economy (PASE) approach towards novel fluorinated 2,2′-bipyridine fluorophores

  摘要：

  An original pot, atom, and step economy (PASE) approach towards novel pentafluorophenyl-substltuted 2,2'-bipyridine fluorophores, as well as their triazine precursors via oxidative transition metal-free C-H/C-Li coupling reactions between 1,2,4-triazines and pentafluorophenyl lithium followed by aza-Diels-Alder reaction has first been reported. This reaction sequence has been found to afford a number of novel pentafiuorophenyl-modified heterocyclic ensembles of various architectures, such as perfluorophenyl-substituted 1,2,4-triazines, their dihydro derivatives, as well as 2,2'-bipyridines in good to excellent yields. The photophysical properties of the synthesized bipyridine fluorophores have been studied, and non-linear optics behavior of the most representative fluorophore has been disclosed on the basis of a positive solvatochromism effect observed. The novel fluorinated 2,2'-bipyridines synthesized are of particular interest in the design of advanced materials for molecular electronics and medicinal chemistry.

  DOI：

  10.1016/j.jfluchem.2019.05.008
• 作为产物：
  描述：

  在 溶剂黄146 作用下， 反应 1.0h， 生成 6-(4''-methoxyphenyl)-3-(2'-quinolyl)-1,2,4-triazine
  参考文献：
  名称：

  Facile synthesis of 6-aryl-3-pyridyl-1,2,4-triazines as a key step toward highly fluorescent 5-substituted bipyridines and their Zn(II) and Ru(II) complexes

  摘要：

  A wide series Of Substituted bipyridines were obtained through the synthesis of 1,2,4-triazines and their aza Diels-Alder reactions. The reported method facilitates the synthesis of functionally diverse bipyridines that provides fine-tuning of photophysical properties of new ligands and their Zn(II) and Ru(II) complexes. Some of substituted bipyridines exhibit 'off-on' fluorescence response toward Zn 2 cations. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.06.040

文献信息

• 5-Aryl-2,2′-bipyridines as tunable fluorophores
  作者：Dmitry N. Kozhevnikov、Olga V. Shabunina、Dmitry S. Kopchuk、Pavel A. Slepukhin、Valery N. Kozhevnikov

  DOI：10.1016/j.tetlet.2006.07.111

  日期：2006.9

  Readily available 5-aryl-2,2'-bipyridines and their derivatives are a unique family of fine-tunable chromophores, where changes in the substitution patterns, solvation and coordination are translated into dramatic spectral changes. They exhibit sensitive and selective response to zinc ions with dramatic increases in emission intensity or significant red-shifts of emission maxima. (c) 2006 Elsevier Ltd. All rights reserved.
• Single-Crystal X-Ray Diffraction Studies in a Series of 5-Pentafluorophenyl-2,2'-bipyridines and Their Fused Analogs
  作者：T. D. Moseev、M.V. Varaksin、E. S. Starnovskaya、D. S. Kopchuk、G. V. Zyryanov、P. A. Slepukhin、O. N. Chupakhin、V. N. Charushin

  DOI：10.1134/s1070363220020115

  日期：2020.2

  Structure of three 6-aryl-5-pentafluorophenyl-2,2'-bipyridines has been studied by means of single-crystal X-ray diffraction analysis. The effect of some functional fragments on the structural organization of compounds, in particular, donor and acceptor substituents in the aryl moiety, as well as annulated benzene and cyclopentane rings on the molecular structure and crystal packing of pentafluorophenyl-modified 2,2'-bipyridine ligand systems has been analyzed.
• Facile synthesis of 6-aryl-3-pyridyl-1,2,4-triazines as a key step toward highly fluorescent 5-substituted bipyridines and their Zn(II) and Ru(II) complexes
  作者：Valery N. Kozhevnikov、Olga V. Shabunina、Dmitry S. Kopchuk、Maria M. Ustinova、Burkhard König、Dmitry N. Kozhevnikov

  DOI：10.1016/j.tet.2008.06.040

  日期：2008.9

  A wide series Of Substituted bipyridines were obtained through the synthesis of 1,2,4-triazines and their aza Diels-Alder reactions. The reported method facilitates the synthesis of functionally diverse bipyridines that provides fine-tuning of photophysical properties of new ligands and their Zn(II) and Ru(II) complexes. Some of substituted bipyridines exhibit 'off-on' fluorescence response toward Zn 2 cations. (C) 2008 Elsevier Ltd. All rights reserved.
• Direct C H/C Li coupling of 1,2,4-triazines with C6F5Li followed by aza-Diels-Alder reaction as a pot, atom, and step economy (PASE) approach towards novel fluorinated 2,2′-bipyridine fluorophores
  作者：Timofey D. Moseev、Mikhail V. Varaksin、Denis A. Gorlov、Egor A. Nikiforov、Dmitry S. Kopchuk、Ekaterina S. Starnovskaya、Albert F. Khasanov、Grigory V. Zyryanov、Valery N. Charushin、Oleg N. Chupakhin

  DOI：10.1016/j.jfluchem.2019.05.008

  日期：2019.8

  An original pot, atom, and step economy (PASE) approach towards novel pentafluorophenyl-substltuted 2,2'-bipyridine fluorophores, as well as their triazine precursors via oxidative transition metal-free C-H/C-Li coupling reactions between 1,2,4-triazines and pentafluorophenyl lithium followed by aza-Diels-Alder reaction has first been reported. This reaction sequence has been found to afford a number of novel pentafiuorophenyl-modified heterocyclic ensembles of various architectures, such as perfluorophenyl-substituted 1,2,4-triazines, their dihydro derivatives, as well as 2,2'-bipyridines in good to excellent yields. The photophysical properties of the synthesized bipyridine fluorophores have been studied, and non-linear optics behavior of the most representative fluorophore has been disclosed on the basis of a positive solvatochromism effect observed. The novel fluorinated 2,2'-bipyridines synthesized are of particular interest in the design of advanced materials for molecular electronics and medicinal chemistry.