2,4,5-三(2-吡啶基)咪唑 | 23974-92-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 2,4,5-三(2-吡啶基)咪唑
• 英文名称: 2,4,5-tris(2-pyridyl)imidazole
• 英文别名: 2,2',2''-(1H-imidazole-2,4,5-triyl)tripyridine；2,4,5-Tris-<2>pyridyl-imidazol；2,4,5-Tris(2-pyridyl)-imidazol；2,2',2''-(1H-imidazole-2,4,5-triyl)-tris-pyridine；2,4,5-Tris(2-pyridyl)imidazole；2-(2,4-dipyridin-2-yl-1H-imidazol-5-yl)pyridine
• CAS: 23974-92-7
• 化学式: C₁₈H₁₃N₅
• 分子量: 299.335
• InChiKey: FCCAYZJCTJTONV-UHFFFAOYSA-N

物化性质

• 沸点：
  558.1±45.0 °C(Predicted)
• 密度：
  1.265±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  67.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,4,5-三(2-吡啶基)咪唑 、 copper dichloride 以 乙醇 为溶剂， 生成 C₁₈H₁₂Cu₂N₅⁽³⁺⁾
  参考文献：
  名称：

  Application of 2,4,5‐tris(2‐pyridyl)imidazole as ‘turn‐off’ fluorescence sensor for Cu(II) and Hg(II) ions and in vitro cell imaging

  摘要：

  2,4,5-三(2-吡啶基)咪唑(L)分子已被评估为在乙醇/HEPES缓冲液（5mM，pH=7.34，1:1，v/v）中用于汞2+和铜2+离子双重传感的探针。探针L在汞2+和铜2+离子同时存在的情况下显示出良好的灵敏度和选择性关闭响应，这在长紫外线照射下是可以理解的。该探针可以在pH值3-11范围内检测铜2+离子，在pH值6-8范围内检测汞2+离子。铜2+的检测限（0.77μM）远低于美国环境保护署规定的允许限值。每升溶液需要两种金属离子（铜2+和汞2+）才能完全淬灭荧光。该探针在用乙二胺四乙酸钠处理时显示出明显的可逆性，使该方案在实际应用中更加经济。用乙醇L溶液涂覆的纸条可以通过荧光强度的可见淬灭来检测样品中铜2+和汞2+离子的存在。密度泛函理论-时间依赖密度泛函理论（DFT-TDDFT）计算支持实验观察，铜2+/汞2+的d轨道提供了非辐射衰变途径。使用HDF和MDA-MB-2

  DOI：

  10.1002/bio.4232
• 作为产物：
  描述：

  2-氰基吡啶 在 十二羰基三钌 、 氢气 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 200.0 ℃ 、413.69 kPa 条件下， 反应 72.0h， 生成 2,4,5-三(2-吡啶基)咪唑
  参考文献：
  名称：

  Hydrogenation of heteroaromatic nitriles and aromatic dinitriles by heterogeneous or homogeneous ruthenium catalysts derived from [Ru 3 (CO) 12 ]

  摘要：

  The use of the complex [Ru-3(CO)(12)] (1) as a catalyst precursor (0.1 mol%) at 200 degrees C, 60 psi of H-2, along with triphenylphosphine (TPP) generated ruthenium nanoparticles (Ru-Nps); this occurred in the presence of pyridine-nitriles leading to a variety of hydrogenation (secondary amine, imine, or imidazole) products, depending of the pyridine-nitrile used, under similar reaction conditions. This relates to relatively good to modest yields, determined by the substituents in the corresponding pyridine. In sharp contrast, the use of aromatic dinitriles did not generate Ru-Nps at 140 degrees C, 150 psi of H-2 and TPP, but allowed the homogeneous catalytic hydrogenation of the 1,4- and 1,3-dicyanobenzenes, to yield the corresponding CN-substituted secondary amine or imine. The main products were characterized by different analytical methods and spectroscopic techniques. (C) 2017 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2017.04.051

文献信息

• Novel synthesis of 2,4-bis(2-pyridyl)-5-(pyridyl)imidazoles and formation of N-(3-(pyridyl)imidazo[1,5-a]pyridine)picolinamidines: nitrogen-rich ligands
  作者：Vijendra Kumar Fulwa、Rojalin Sahu、Himanshu Sekhar Jena、Vadivelu Manivannan

  DOI：10.1016/j.tetlet.2009.09.002

  日期：2009.11

  5-tris(2-pyridyl)imidazole (1a) as the major product and N-(3-(2-pyridyl)imidazo[1,5-a]pyridine)picolinamidine (2a) in small amounts. Similarly, by using 3-picolylamine, 2,4,-bis(2-pyridyl)-5-(3-pyridyl)imidazole (1b) and N-(3-(3-pyridyl)imidazo[1,5-a]pyridine)picolinamidine (2b) were isolated, and by using 4-picolylamine, 2,4,-bis(2-pyridyl)-5-(4-pyridyl)imidazole (1c) and N-(3-(4-pyridyl)imidazo[1,5

  加热纯的2-picolylamine和2-cyanopyridine的1：2混合物，然后用KOH水溶液处理所得的红色胶状物质，分离出2,4,5-tris（2-吡啶基）咪唑（1a）作为主要产物和少量N-（3-（2-吡啶基）咪唑并[1,5- a ]吡啶）吡啶啉am（2a）。类似地，通过使用3-甲基吡啶胺，2,4，-双（2-吡啶基）-5-（3-吡啶基）咪唑（1b）和N-（3-（3-吡啶基）咪唑[1,5- a ]分离吡啶）吡啶啉am（2b），并使用4-吡啶甲基胺，2,4，-双（2-吡啶基）-5-（4-吡啶基）咪唑（1c）和N-（3-（4-吡啶基）咪唑[1,5-分离出[ ]吡啶）吡啶啉am（2c）。描绘了1a – c和2a – c形成的合理机制。
• Hydrogenation of heteroaromatic nitriles and aromatic dinitriles by heterogeneous or homogeneous ruthenium catalysts derived from [Ru 3 (CO) 12 ]
  作者：Juventino J. García、Nora Pérez-Lezama、Alma Arévalo

  DOI：10.1016/j.ica.2017.04.051

  日期：2017.8

  The use of the complex [Ru-3(CO)(12)] (1) as a catalyst precursor (0.1 mol%) at 200 degrees C, 60 psi of H-2, along with triphenylphosphine (TPP) generated ruthenium nanoparticles (Ru-Nps); this occurred in the presence of pyridine-nitriles leading to a variety of hydrogenation (secondary amine, imine, or imidazole) products, depending of the pyridine-nitrile used, under similar reaction conditions. This relates to relatively good to modest yields, determined by the substituents in the corresponding pyridine. In sharp contrast, the use of aromatic dinitriles did not generate Ru-Nps at 140 degrees C, 150 psi of H-2 and TPP, but allowed the homogeneous catalytic hydrogenation of the 1,4- and 1,3-dicyanobenzenes, to yield the corresponding CN-substituted secondary amine or imine. The main products were characterized by different analytical methods and spectroscopic techniques. (C) 2017 Elsevier B.V. All rights reserved.
• Application of 2,4,5‐tris(2‐pyridyl)imidazole as ‘turn‐off’ fluorescence sensor for Cu(II) and Hg(II) ions and <i>in vitro</i> cell imaging
  作者：Araghni Bhattacharya、Satyajit Mahata、Ashutosh Bandyopadhyay、Biman B. Mandal、Vadivelu Manivannan

  DOI：10.1002/bio.4232

  日期：2022.6

  The 2,4,5-tris(2-pyridyl)imidazole (L) molecule has been evaluated as a probe for dual sensing of Hg2+ and Cu2+ ions in EtOH/HEPES buffer medium (5 mM, pH = 7.34, 1:1, v/v). Probe L shows a good sensitive and selective turn-off response in the presence of both Hg2+ and Cu2+ ions, which is comprehensible under long UV light. The probe can detect Cu2+ ion in the pH range 3–11 and Hg2+ ion in pH 6–8. The limit of detection for Cu2+ (0.77 μM) is well under the allowable limit prescribed by the United States Environmental Protection Agency. Two metal (Cu2+/Hg2+) ions are needed per L for complete fluorescence quenching. The probe shows marked reversibility on treatment with Na2EDTA, making the protocol more economical for practical purposes. Paper strip coated with the L solution of EtOH can detect the presence of Cu2+ and Hg2+ ions in the sample using visible quenching of the fluorescence intensity. Density functional theory–time-dependent density functional theory (DFT–TDDFT) calculations support experimental observations, and d-orbitals of Cu2+/Hg2+ provide a nonradiative decay pathway. Cell imaging study using HDF and MDA-MB-231 cells also supported the viability of L in detecting Cu2+ and Hg2+ ions in living cells.

  2,4,5-三(2-吡啶基)咪唑(L)分子已被评估为在乙醇/HEPES缓冲液（5mM，pH=7.34，1:1，v/v）中用于汞2+和铜2+离子双重传感的探针。探针L在汞2+和铜2+离子同时存在的情况下显示出良好的灵敏度和选择性关闭响应，这在长紫外线照射下是可以理解的。该探针可以在pH值3-11范围内检测铜2+离子，在pH值6-8范围内检测汞2+离子。铜2+的检测限（0.77μM）远低于美国环境保护署规定的允许限值。每升溶液需要两种金属离子（铜2+和汞2+）才能完全淬灭荧光。该探针在用乙二胺四乙酸钠处理时显示出明显的可逆性，使该方案在实际应用中更加经济。用乙醇L溶液涂覆的纸条可以通过荧光强度的可见淬灭来检测样品中铜2+和汞2+离子的存在。密度泛函理论-时间依赖密度泛函理论（DFT-TDDFT）计算支持实验观察，铜2+/汞2+的d轨道提供了非辐射衰变途径。使用HDF和MDA-MB-2

表征谱图