methyl 6-(6-phenyl-1,2,4-triazin-3-yl)picolinate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: methyl 6-(6-phenyl-1,2,4-triazin-3-yl)picolinate
• 英文别名: 3-(6-methoxycarbonyl-2-pyridyl)-6-phenyl-1,2,4-triazine；methyl 6-(6-phenyl-1,2,4-triazin-3-yl)pyridine-2-carboxylate；Methyl 6-(6-phenyl-1,2,4-triazin-3-yl)pyridine-2-carboxylate
• 化学式: C₁₆H₁₂N₄O₂
• 分子量: 292.297
• InChiKey: WIMOWKIXLFHZDT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  77.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 6-(6-phenyl-1,2,4-triazin-3-yl)picolinate 在 sodium tetrahydroborate 、 三溴化磷 作用下， 以 乙醇 、 二氯甲烷 、 邻二甲苯 为溶剂， 反应 58.0h， 生成 6’-bromomethyl-5-phenyl-2,2’-bipyridine
  参考文献：
  名称：

  基于5-芳基-2,2'-联吡啶的锌（II）ICT-PET荧光探针的设计

  摘要：

  利用二聚烯丙基氨基甲基片段修饰的5-芳基-2,2'-联吡啶的合成和应用说明了利用PET和ICT感应机制对Zn（II）阳离子选择性和敏感的“关闭”荧光探针的合理设计。 。芳基取代基提供了性质的调节。

  DOI：

  10.1016/j.tetlet.2012.09.027
• 作为产物：
  描述：

  alpha-溴-4-甲氧基苯乙酮 、 6-methoxycarbonyl-2-pyridinecarboxylic acid hydrazide 在 sodium acetate 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 15.0h， 以22%的产率得到methyl 6-(6-phenyl-1,2,4-triazin-3-yl)picolinate
  参考文献：
  名称：

  1,2,4-三嗪联吡啶配体合成方法制备新型发光Eu（III）配合物

  摘要：

  事实证明，用于合成功能化联吡啶配体的“三嗪”方法是制备发光Eu（III）配合物的便捷方法。该方法允许通过控制光物理性质灵活地构建生色团和配位体。以此方式制备的（III）络合物[ Eu1 ] – [ Eu5 ]在水性介质中表现出强烈的长寿命以金属为中心的发光。在联吡啶的5位上的芳族取代基对发光参数具有显着影响，并用于引入生物缀合的功能。带有伯胺基团的配合物[ Eu4 ]和[ Eu5 ]是现成的发光“标签”，用于肽标记。

  DOI：

  10.1016/j.tet.2010.11.058

文献信息

• Asymmetrically substituted 5,5′′-diaryl-2,2′:6′,2′′-terpyridines as efficient fluorescence “turn-on” probes for Zn2+ in food/cosmetic samples and human urine
  作者：Olga V. Shabunina、Ekaterina S. Starnovskaya、Yaroslav K. Shaitz、Dmitry S. Kopchuk、Leila K. Sadieva、Grigory A. Kim、Olga S. Taniya、Igor L. Nikonov、Sougata Santra、Grigory V. Zyryanov、Valery N. Charushin

  DOI：10.1016/j.jphotochem.2020.113101

  日期：2021.3
• Novel neutral lanthanide complexes of 5-aryl-2,2′-bipyridine-6′-carboxylic acids with improved photophysical properties
  作者：Dmitry S. Kopchuk、Alexey P. Krinochkin、Dmitry N. Kozhevnikov、Pavel A. Slepukhin

  DOI：10.1016/j.poly.2016.07.025

  日期：2016.11

  By means of "1,2,4-triazine" strategy new 2,2'-bipyridine-type lanthanide ligands, i.e. 5-aryl-2,2'-bipyridine-6'-carboxylic acids and its cycloalkane-annulated derivatives, i.e. 6-(4-aryl-6,7-dihydro-5H-cyclopenta[c]pyridin-1-yl)picolinic acids, have been synthesized, and their luminescent neutral lanthanide complexes have been prepared. Due to the presence of an annulated cyclopentene fragment the last ligand lanthanide complexes exhibited high solubility in non-polar solvents. In comparison with early published chelates the herein reported complexes exhibit improved photophysical properties in non polar solvents namely more pronounced bathochromic shift in absorption spectra and higher europium luminescence quantum yields. The structures of two europium complexes have been confirmed based on X-ray diffraction analysis. (C) 2016 Elsevier Ltd. All rights reserved.
• A Modified Synthesis of 6-Aryl-3-(6-R-pyridin-2-yl)-1,2,4-triazines
  作者：O. V. Shabunina、E. S. Starnovskaya、Ya. K. Shtaits、D. S. Kopchuk、I. S. Kovalev、G. V. Zyryanov、V. L. Rusinov、O. N. Chupakhin

  DOI：10.1134/s107042801810024x

  日期：2018.10

  A practical procedure has been proposed for the synthesis of 6-aryl-3-(pyridin-2-yl)-1,2,4-triazines containing various functional groups in the -position of the pyridine ring by direct heterocyclization of isonitrosoacetophenone hydrazones with 6-substituted pyridine-2-carbaldehydes.
• 1,2,4-Triazine method of bipyridine ligand synthesis for the preparation of new luminescent Eu(III) complexes
  作者：Anton M. Prokhorov、Valery N. Kozhevnikov、Dmitry S. Kopchuk、Hélène Bernard、Nathalie Le Bris、Raphaël Tripier、Henri Handel、Burkhard Koenig、Dmitry N. Kozhevnikov

  DOI：10.1016/j.tet.2010.11.058

  日期：2011.1

  the synthesis of functionalized bipyridine ligands proved to be a convenient method for the preparation of luminescent Eu(III) complexes. The approach allows flexible construction of chromophore and coordination sphere with control of photophysical properties. Europium(III) complexes [Eu1]–[Eu5] prepared in this way exhibit intense long-life metal-centered luminescence in aqueous media. The aromatic substituent

  事实证明，用于合成功能化联吡啶配体的“三嗪”方法是制备发光Eu（III）配合物的便捷方法。该方法允许通过控制光物理性质灵活地构建生色团和配位体。以此方式制备的（III）络合物[ Eu1 ] – [ Eu5 ]在水性介质中表现出强烈的长寿命以金属为中心的发光。在联吡啶的5位上的芳族取代基对发光参数具有显着影响，并用于引入生物缀合的功能。带有伯胺基团的配合物[ Eu4 ]和[ Eu5 ]是现成的发光“标签”，用于肽标记。
• Design of ICT-PET fluorescent probes for zinc(II) based on 5-aryl-2,2′-bipyridines
  作者：Dmitry S. Kopchuk、Anton M. Prokhorov、Pavel A. Slepukhin、Dmitry N. Kozhevnikov

  DOI：10.1016/j.tetlet.2012.09.027

  日期：2012.11

  Rational design of selective and sensitive ‘off-on’ fluorescent probes for Zn(II) cations exploiting both PET and ICT mechanisms of sensing is illustrated by the synthesis and application of 5-aryl-2,2′-bipyridines modified with a dipicolylaminomethyl fragment. The aryl substituent provides tuning of the properties.

  利用二聚烯丙基氨基甲基片段修饰的5-芳基-2,2'-联吡啶的合成和应用说明了利用PET和ICT感应机制对Zn（II）阳离子选择性和敏感的“关闭”荧光探针的合理设计。 。芳基取代基提供了性质的调节。