6-(2-naphthyl)-3-(2-pyridyl)-1,2,4-triazine | 1041285-65-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 6-(2-naphthyl)-3-(2-pyridyl)-1,2,4-triazine
• 英文别名: 6-Naphthalen-2-yl-3-pyridin-2-yl-1,2,4-triazine；6-naphthalen-2-yl-3-pyridin-2-yl-1,2,4-triazine
• CAS: 1041285-65-7
• 化学式: C₁₈H₁₂N₄
• 分子量: 284.32
• InChiKey: JAZCFXNLUZWBHU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  51.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-(2-naphthyl)-3-(2-pyridyl)-1,2,4-triazine 、 五氟苯 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.67h， 以77%的产率得到6-(naphthalen-2-yl)-5-(perfluorophenyl)-3-(pyridin-2-yl)-4,5-dihydro-1,2,4-triazine
  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：

  6-naphthalen-2-yl-3-pyridin-2-yl-3H-[1,2,4]triazin-4-ol 在 溶剂黄146 作用下， 反应 1.0h， 生成 6-(2-naphthyl)-3-(2-pyridyl)-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

• From 1,2,4-triazines towards substituted pyridines and their cyclometallated Pt complexes
  作者：Valery N. Kozhevnikov、Maria M. Ustinova、Pavel A. Slepukhin、Amedeo Santoro、Duncan W. Bruce、Dmitry N. Kozhevnikov

  DOI：10.1016/j.tetlet.2008.04.138

  日期：2008.6

  A new, efficient methodology for the synthesis of substituted thienylpyridines includes the synthesis of 3-thienyl-1,2,4-triazines using simple heterocyclisation followed by easy transformation of the triazine ring to a pyridine through an aza Diels–Alder approach. A variety of substituted pyridines can be easily achieved using cheap, commercially available reagents such as bromoacetylarenes, aroyl

  一种新的，有效的取代噻吩基吡啶合成方法包括使用简单的杂环化合成3-噻吩基-1,2,4-三嗪，然后通过aza Diels-Alder方法将三嗪环轻松转化为吡啶。使用便宜的，可商购的试剂，例如溴乙酰芳烃，芳酰肼，降冰片二烯和烯胺以各种组合，可以容易地实现多种取代的吡啶。新的噻吩基吡啶形成磷光环金属化的Pt配合物。
• 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.