6-(4-fluorophenyl)-3-(pyridin-2-yl)-1,2,4-triazine | 850089-98-4

• 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: 6-(4-fluorophenyl)-3-(pyridin-2-yl)-1,2,4-triazine
• 英文别名: 6-(4-Fluorophenyl)-3-pyridin-2-yl-1,2,4-triazine
• CAS: 850089-98-4
• 化学式: C₁₄H₉FN₄
• 分子量: 252.251
• InChiKey: CGQSQACCQFEZNK-UHFFFAOYSA-N

物化性质

• 沸点：
  478.2±48.0 °C(Predicted)
• 密度：
  1.279±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• 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：
  5

反应信息

• 作为反应物：
  描述：

  五氟苯 、 6-(4-fluorophenyl)-3-(pyridin-2-yl)-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 6-(4-fluorophenyl)-5-(perfluorophenyl)-3-(pyridin-2-yl)-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：

  吡啶-2-甲醛 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 生成 6-(4-fluorophenyl)-3-(pyridin-2-yl)-1,2,4-triazine
  参考文献：
  名称：

  An efficient route to 5-(hetero)aryl-2,4′- and 2,2′-bipyridines through readily available 3-pyridyl-1,2,4-triazines

  摘要：

  A new route to substituted bipyridines based on a new method for the synthesis of substituted 3-pyridyl-1,2,4-triazines and their aza-Diels-Alder reactions is shown to be an efficient strategy for the preparation of structurally diverse bipyridine ligands. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.01.135

文献信息

• Studies on the interactions of 5-<i>R</i>-3-(2-pyridyl)-1,2,4-triazines with arynes: inverse demand aza-Diels–Alder reaction <i>versus</i> aryne-mediated domino process
  作者：Dmitry S. Kopchuk、Igor L. Nikonov、Albert F. Khasanov、Kousik Giri、Sougata Santra、Igor S. Kovalev、Emiliya V. Nosova、Sravya Gundala、Padmavathi Venkatapuram、Grigory V. Zyryanov、Adinath Majee、Oleg N. Chupakhin

  DOI：10.1039/c8ob00847g

  日期：——

  aza-Diels–Alder products or 1,2,4-triazine ring rearrangement (domino) products as major ones depending on the nature of both the substituents at the C5 position of the 1,2,4-triazine core or in the aryne moiety. The structures of the key products were confirmed based on X-ray data. Based on the density functional theoretical (DFT) studies of the Diels–Alder transition state geometries, the influence of the nature

  已经研究了取代的5 - R -3-（吡啶基-2）-1,2,4-三嗪与原位生成的取代的芳烃中间体之间的相互作用。根据1,2,5碳原子上两个取代基的性质，反应可提供反需求（ID）的aza-Diels-Alder产品或1,2,4-三嗪环重排（domino）产品作为主要产品。 4-三嗪核或在芳烃部分。根据X射线数据确定了关键产品的结构。基于Diels–Alder过渡态几何的密度泛函理论（DFT）研究，提出了芳烃性质对1,2,4-三嗪转化方向的影响。
• Aryne approach towards 2,3-difluoro-10-(1H-1,2,3-triazol-1-yl)pyrido[1,2-a]indoles
  作者：Dmitry S. Kopchuk、Igor L. Nikonov、Grigory V. Zyryanov、Emiliya V. Nosova、Igor S. Kovalev、Pavel A. Slepukhin、Vladimir L. Rusinov、Oleg N. Chupakhin

  DOI：10.1016/j.mencom.2015.01.003

  日期：2015.1

  Reaction between 3-(2-pyridyl)-1,2,4-triazines and in situ generated 4,5-difluorobenzyne in toluene affords 2,3-difluoro-10-(1H-1,2,3-triazol-1-yl)pyrido[1,2-a]indoles. The structure of one representative compound was confirmed by X-ray diffraction analysis.
• 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.