1-methyl-2-(4-methylpyridin-2-yl)-1H-benzimidazole | 200863-73-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 1-methyl-2-(4-methylpyridin-2-yl)-1H-benzimidazole
• 英文别名: 2-(4-methylpyridin-2-yl)-1-methyl-1H-benzo[d]imidazole；1-methyl-2-(4-methylpyridin-2-yl)-1H-benzo[d]imidazole；1-methyl-2-(4-methyl-pyridin-2-yl)-1H-benzoimidazole；1-Methyl-2-(4-methylpyridin-2-yl)benzimidazole
• CAS: 200863-73-6
• 化学式: C₁₄H₁₃N₃
• 分子量: 223.277
• InChiKey: GKTLLTVHVYZMOS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  30.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  五羰基氯铼(I) 、 1-methyl-2-(4-methylpyridin-2-yl)-1H-benzimidazole 以 甲苯 为溶剂， 以59%的产率得到fac-[tricarbonylrhenium(2-(4-methylpyridin-2-yl)-1-methyl-1H-benzo[d]imidazole)Cl]
  参考文献：
  名称：

  Photophysical properties and computational investigations of tricarbonylrhenium(I)[2-(4-methylpyridin-2-yl)benzo[d]-X-azole]L and tricarbonylrhenium(I)[2-(benzo[d]-X-azol-2-yl)-4-methylquinoline]L derivatives (X=N–CH3, O, or S; L=Cl−, pyridine)

  摘要：

  We report a combined experimental and computational study of new rhenium tricarbonyl complexes based on the bidentate heterocyclic N-N ligands 2-(4-methylpyridin-2-yl)benzo[d]-X-azole (X = N-CH3, O, or S) and 2-(benzo[d]-X-azol-2-yl)-4-methylquinoline (X = N-CH3, O, or S). Two sets of complexes are reported. Chloro complexes, described by the general formula Re(CO)(3)[2-(4-methylpyridin-2-yl)benzo[d]-X-azole]Cl (X = N-CH3, 1; X = 0, 2; X = S, 3) and Re(CO)3[2-(benzo[c -X-azol-2-yl)-4-methylquinoline]Cl (X = N-CH3, 4; X = O, 5; X = S, 6) were synthesized heating at reflux Re(CO)(5)Cl with the appropriate N-N ligand in toluene. The corresponding pyridine set {Re(CO)(3)[2-(4-methylpyridin-2-yl)benzo-X-azole]py}PF6 (X = N-CH3, 7; X = O, 8; X = S, 9) and (Re(CO)(3)[2-(benzo[d]-X-azol-2-yl)-4-methylquinoline]py)PF6(X = N-CH3, 10; X = O, 11; X = S, 12) was synthesized by halide abstraction with silver nitrate of 1-6 followed by heating in pyridine and isolated as their hexafluorophosphate salts. All complexes have been fully characterized by IR, NMR, electrochemical techniques and luminescence. The crystal structures of I and 7 were obtained by X-ray diffraction. DFT and time-dependent (TD) DFT calculations were carried out for investigating the effect of the organic ligand on the optical properties and electronic structure of the reported complexes. (C) 2006 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2006.11.004
• 作为产物：
  描述：

  4-甲基-2-(2-苯并咪唑基)吡啶 、 碘甲烷 在 18-冠醚-6 、 potassium tert-butylate 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以85%的产率得到1-methyl-2-(4-methylpyridin-2-yl)-1H-benzimidazole
  参考文献：
  名称：

  杂环系统的伏安行为。吡啶基取代的苯并咪唑，苯并恶唑和苯并噻唑

  摘要：

  对于一系列18个吡啶基取代的杂环碱[苯并咪唑，苯并恶唑和苯并噻唑]，已研究了在滴下的汞电极上测得的伏安特性。还研究了通过与碘甲烷反应获得的相应的季盐。发现还原电位取决于苯并咪唑，苯并恶唑或苯并噻唑部分的性质及其在吡啶环上的位置以及正电荷的存在。发现伏安波的可逆性是系统结构的函数。还研究了质子供体对碱的伏安行为的影响。

  DOI：

  10.1002/jhet.5570340517

文献信息

• Synthesis, Electrochemical and Electrogenerated Chemiluminescence Studies of Ruthenium(II) Bis(2,2′‐bipyridyl){2‐(4‐methylpyridin‐2‐yl)benzo[ <i>d</i> ]‐X‐azole} Complexes
  作者：Roberto Gobetto、Giuseppe Caputo、Claudio Garino、Simona Ghiani、Carlo Nervi、Luca Salassa、Edward Rosenberg、J. B. Alexander Ross、Guido Viscardi、Gianmario Martra、Ivana Miletto、Marco Milanesio

  DOI：10.1002/ejic.200600099

  日期：2006.7

  one-electron oxidation process that are chemically and electrochemically reversible. In all cases, electrogenerated chemiluminescence (ECL) has been observed in the presence of the co-reactant tri-n-propylamine (TPA). An analogue of 1 has been synthesized, [RuIIbis(bipyridyl)2-(4-methylpyridin-2-yl)benzo[d]-X-azole}](PF6)2 [X = N(CH2)5CO2H, 4], it has been coupled with bovine serum albumin (BSA), and

  [RuIIbis(bipyridyl)2-(4-methylpyridin-2-yl)benzo[d]-X-azole}](PF6)2 (X = N–CH3, 1; S, 2;或 O, 3) 已被合成并通过质子和 13C NMR 光谱和 UV/Vis 光谱充分表征。还报告了 1 的 X 射线结构。已经研究了 1-3 的电化学行为和光物理性质。循环伏安法 (CV) 揭示了三个连续的单电子还原过程和一个单电子氧化过程的存在，这些过程在化学和电化学上都是可逆的。在所有情况下，在共反应物三正丙胺 (TPA) 存在下都观察到了电致化学发光 (ECL)。已合成 1 的类似物，[RuIIbis(bipyridyl)2-(4-methylpyridin-2-yl)benzo[d]-X-azole}](PF6)2 [X = N(CH2)5CO2H, 4] , 它已与牛血清白蛋白 (BSA) 结合，并研究了其光物理特性。(©
• Luminescent Compounds Having a Functionalized Linker Arm Used in the Bioconjugation and Labeling of Biomolecules
  申请人：Caputo Giuseppe

  公开号：US20070231818A1

  公开（公告）日：2007-10-04

  The present invention relates to luminescent compounds having a functionalised linker arm, their synthesis and use in bioconjugation and labelling of biomolecules, such as for example nucleosides, nucleotides, nucleic acids (DNA, RNA or PNA) and proteins, as well as their use in the execution of in vitro and in vivo analytic and diagnostic assays.

  本发明涉及具有功能化连接臂的发光化合物，它们的合成以及在生物共轭和生物分子标记中的应用，例如核苷、核苷酸、核酸（DNA、RNA或PNA）和蛋白质，以及它们在体外和体内分析和诊断检测中的应用。
• LUMINESCENT COMPOUNDS HAVING A FUNCTIONALISED LINKER ARM USED IN THE BIOCONJUGATION AND LABELLING OF BIOMOLECULES
  申请人：Caputo, Giuseppe

  公开号：EP1759204B1

  公开（公告）日：2008-11-26
• US7750157B2
  申请人：——

  公开号：US7750157B2

  公开（公告）日：2010-07-06
• Photophysical properties and computational investigations of tricarbonylrhenium(I)[2-(4-methylpyridin-2-yl)benzo[d]-X-azole]L and tricarbonylrhenium(I)[2-(benzo[d]-X-azol-2-yl)-4-methylquinoline]L derivatives (X=N–CH3, O, or S; L=Cl−, pyridine)
  作者：Andrea Albertino、Claudio Garino、Simona Ghiani、Roberto Gobetto、Carlo Nervi、Luca Salassa、Edward Rosenberg、Ayesha Sharmin、Guido Viscardi、Roberto Buscaino、Gianluca Croce、Marco Milanesio

  DOI：10.1016/j.jorganchem.2006.11.004

  日期：2007.2

  We report a combined experimental and computational study of new rhenium tricarbonyl complexes based on the bidentate heterocyclic N-N ligands 2-(4-methylpyridin-2-yl)benzo[d]-X-azole (X = N-CH3, O, or S) and 2-(benzo[d]-X-azol-2-yl)-4-methylquinoline (X = N-CH3, O, or S). Two sets of complexes are reported. Chloro complexes, described by the general formula Re(CO)(3)[2-(4-methylpyridin-2-yl)benzo[d]-X-azole]Cl (X = N-CH3, 1; X = 0, 2; X = S, 3) and Re(CO)3[2-(benzo[c -X-azol-2-yl)-4-methylquinoline]Cl (X = N-CH3, 4; X = O, 5; X = S, 6) were synthesized heating at reflux Re(CO)(5)Cl with the appropriate N-N ligand in toluene. The corresponding pyridine set Re(CO)(3)[2-(4-methylpyridin-2-yl)benzo-X-azole]py}PF6 (X = N-CH3, 7; X = O, 8; X = S, 9) and (Re(CO)(3)[2-(benzo[d]-X-azol-2-yl)-4-methylquinoline]py)PF6(X = N-CH3, 10; X = O, 11; X = S, 12) was synthesized by halide abstraction with silver nitrate of 1-6 followed by heating in pyridine and isolated as their hexafluorophosphate salts. All complexes have been fully characterized by IR, NMR, electrochemical techniques and luminescence. The crystal structures of I and 7 were obtained by X-ray diffraction. DFT and time-dependent (TD) DFT calculations were carried out for investigating the effect of the organic ligand on the optical properties and electronic structure of the reported complexes. (C) 2006 Elsevier B.V. All rights reserved.