6-tolyl-3-(2'-pyridyl)-1,2,4-triazine | 850089-96-2

• 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-tolyl-3-(2'-pyridyl)-1,2,4-triazine
• 英文别名: 6-p-tolyl-3-(2-pyridyl)-1,2,4-triazine；3-(pyridin-2-yl)-6-(p-tolyl)-1,2,4-triazine；6-(4-Methylphenyl)-3-pyridin-2-yl-1,2,4-triazine
• CAS: 850089-96-2
• 化学式: C₁₅H₁₂N₄
• 分子量: 248.287
• InChiKey: FUXIWAJWKUPAMY-UHFFFAOYSA-N

物化性质

• 熔点：
  164-166 °C
• 沸点：
  485.6±37.0 °C(Predicted)
• 密度：
  1.186±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 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-tolyl-3-(2'-pyridyl)-1,2,4-triazine 以 乙醇 、 邻二甲苯 为溶剂， 反应 20.0h， 生成
  参考文献：
  名称：

  基于 5-Aryl-2,2'-联吡啶及其杂配体水杨酸金属配合物的有前途的抗真菌和抗菌剂：合成、生物评价、分子对接

  摘要：

  迎接挑战：合成了一系列新的 5-aryl-2,2'-bipyridines 及其（多氟）水杨酸盐金属配合物。它们的抗菌活性在体外对八种皮肤癣菌、七种念珠菌、八种革兰氏阳性菌和两种革兰氏阴性菌进行了评估。使用分子对接，我们提出抗葡萄球菌作用是通过先导化合物对金黄色葡萄球菌DNA 促旋酶 GyrB 的抑制机制进行的。

  DOI：

  10.1002/cmdc.202100577
• 作为产物：
  描述：

  4-methyl-α-oximinoacetophenone hydrazone 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 生成 6-tolyl-3-(2'-pyridyl)-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

• 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.
• A rational protocol for the synthesis of 1-(2-pyridyl)isoquinolines
  作者：Dmitry S. Kopchuk、Igor S. Kovalev、Albert F. Khasanov、Grigory V. Zyryanov、Pavel A. Slepukhin、Vladimir L. Rusinov、Oleg N. Chupakhin

  DOI：10.1016/j.mencom.2013.05.007

  日期：2013.5

  Aza-Diels-Alder reaction between 3-(2-pyridyl)-1,2,4-triazines and 1-morpholinocyclohexene followed by aromatization of the cyclohexene moiety affords 1-(2-pyridyl)isoquinolines. Crystal structures of two tetrahydroisoquinolines were confirmed by X-ray diffraction analysis.
• Reactions of 5-(1,2-Dicarbadodecaboran-1-yl)-3-(2-pyridyl)-1,2,4-triazines with Dienophiles
  作者：M. I. Valieva、A. Rammohan、E. S. Starnovskaya、E. A. Kudryashova、A. P. Krinochkin、D. S. Kopchuk、G. V. Zyryanov、O. N. Chupakhin

  DOI：10.1134/s1070363223030064

  日期：2023.3
• Promising Antifungal and Antibacterial Agents Based on 5‐Aryl‐2,2′‐bipyridines and Their Heteroligand Salicylate Metal Complexes: Synthesis, Bioevaluation, Molecular Docking
  作者：Yanina Burgart、Evgeny Shchegolkov、Irina Shchur、Dmitry Kopchuk、Natalia Gerasimova、Sophia Borisevich、Natalia Evstigneeva、Grigory Zyryanov、Maria Savchuk、Maria Ulitko、Natalia Zilberberg、Nikolai Kungurov、Victor Saloutin、Valery Charushin、Oleg Chupakhin

  DOI：10.1002/cmdc.202100577

  日期：2022.2.4

  challenge: A series of new 5-aryl-2,2′-bipyridines and their (polyfluoro)salicylate metal complexes was synthesized. Their antimicrobial activity was evaluated in vitro against eight strains of dermatophytes, seven strains of Candida yeasts, eight strains of Gram-positive and two strains of Gram-negative bacteria. Using molecular docking, we proposed that anti-staphylococcal action proceeds through the inhibition

  迎接挑战：合成了一系列新的 5-aryl-2,2'-bipyridines 及其（多氟）水杨酸盐金属配合物。它们的抗菌活性在体外对八种皮肤癣菌、七种念珠菌、八种革兰氏阳性菌和两种革兰氏阴性菌进行了评估。使用分子对接，我们提出抗葡萄球菌作用是通过先导化合物对金黄色葡萄球菌DNA 促旋酶 GyrB 的抑制机制进行的。