5-(1H-imidazol-1-yl)pyrimidine | 1079394-95-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 5-(1H-imidazol-1-yl)pyrimidine
• 英文别名: 5-(1-imidazolyl)pyrimidine；N-(pyrimidin-2-yl)imidazole；(pyrimidin-5-yl)-1H-imidazole；5-imidazol-1-ylpyrimidine
• CAS: 1079394-95-8
• 化学式: C₇H₆N₄
• mdl: MFCD22056416
• 分子量: 146.151
• InChiKey: CMFLBNYJJCTWSD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  43.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-(1H-imidazol-1-yl)pyrimidine 在 silver(l) oxide 作用下， 以 四氢呋喃 、 乙二醇乙醚 为溶剂， 反应 24.0h， 生成
  参考文献：
  名称：

  N-Heterocyclic Carbenes: Versatile Second Cyclometalated Ligands for Neutral Iridium(III) Heteroleptic Complexes

  摘要：

  With 2-(2,4-difluorophenyl)pyridine (dfppy) as the first cyclometalated ligand and different monoanionic N-heterocyclic carbenes (NHCs) as the second cyclometalated ligands, 16 blue or greenish-blue neutral iridium(III) phosphorescent complexes, (dfppy)(2)Ir(NHC), were synthesized efficiently. The obtained Ir(III) complexes display typical phosphorescence of 455-485 nm with quantum yields up to 0.73. By modifying the phenyl moiety in the NHCs with electron-withdrawing substituents (e.g., -F or -CF3) or replacing it with N-heteroaromatic rings (pyridine or pyrimidine), the HOMO-LUMO gaps are broadened, and the emissions shift to the more blue region accordingly. Furthermore, to extend the application scope of NHCs as the second cyclometalated ligands, five other Ir(III) complexes from blue to red were synthesized with different first cyclometalated ligands. Finally, the organic light-emitting diodes using one blue emitter exhibit a maximum current efficiency of 37.83 cd A(-1), an external quantum efficiency of 10.3%, and a maximum luminance of 8709 cd m(-2). Our results demonstrate that NHCs as the second cyclometalated ligands are good candidates for the achievement of efficient phosphorescent Ir-III complexes and corresponding devices.

  DOI：

  10.1021/ic501949h
• 作为产物：
  描述：

  咪唑 、 5-溴嘧啶 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 以87%的产率得到5-(1H-imidazol-1-yl)pyrimidine
  参考文献：
  名称：

  超顺磁性Fe 3 O 4 @SiO 2纳米颗粒上负载的Cu（II）Salen络合物：咪唑与芳基卤化物进行N-芳基化反应的高效且可磁回收的催化剂

  摘要：

  摘要据报道，Fe 3 O 4 @SiO 2 / Salen-Cu（II）纳米催化剂是一种热和空气稳定，经济，可磁回收的非均相催化剂，用于咪唑的选择性和有效的N-（杂）芳基化。仅通过向反应物中添加少量催化剂（0.4 mol％Cu）并在空气中加热，新提出的方法即可提供多种功能化和受阻的氮-（杂）芳基咪唑在较短的反应时间内即可获得良好至极好的收率。借助永磁体可以很容易地回收催化剂，并且可以连续使用多达五次而又不会明显丧失活性。而且，在第五次循环之后，铜的浸出量可以忽略不计。特别地，使用（杂）芳基碘化物或溴化物作为芳基化剂，并且仅需要少量的可磁回收的非均相铜基纳米催化剂使该方法低成本，对环境无害且易于使用。 图形概要

  DOI：

  10.1007/s00706-018-2148-4

文献信息

• AZABICYCLO COMPOUND AND SALT THEREOF
  申请人：Kitade Makoto

  公开号：US20120108589A1

  公开（公告）日：2012-05-03

  It is intended to provide a novel azabicyclo compound which exhibits both HSP90 inhibitory activity and cell proliferation inhibitory effect. Specifically disclosed is a compound represented by the following general formula (I) or a salt thereof: wherein X 1 represents CH or N; any one of X 2 , X 3 and X 4 represents N, and the others represent CH; any one or two of Y 1 , Y 2 , Y 3 and Y 4 represent C—R 4 , and the others are the same or different and represent CH or N; R 1 represents an optionally substituted monocyclic or bicyclic unsaturated heterocyclic group having 1 to 4 heteroatoms selected from N, S and O; R 2 represents an alkyl group having 1 to 6 carbon atoms, or the like; and R 3 and R 4 represent —CO—R 5 or the like.

  本发明旨在提供一种新型的azabicyclo化合物，其具有HSP90抑制活性和细胞增殖抑制作用。具体公开的是以下一般式(I)或其盐所代表的化合物：其中X1代表CH或N；X2、X3和X4中的任意一个代表N，其他代表CH；Y1、Y2、Y3和Y4中的一个或两个代表C—R4，其他者相同或不同，代表CH或N；R1代表1至4个异原子（N、S和O）的单环或双环不饱和杂环基，可选地取代；R2代表具有1至6个碳原子的烷基基团等；R3和R4代表—CO—R5或类似物。
• Synthesis and Characterization of Nickel Inverse 9-Metallacrown-3, Palladium–Silver, and Dinuclear Platinum Complexes Containing Pyrazole-Functionalized NHC Ligands
  作者：Chao Chen、Huayu Qiu、Wanzhi Chen

  DOI：10.1021/ic2012233

  日期：2011.9.5

  metallacrown nickel complexes [Ni3(μ-OH)(L1)3](PF6)2 (1, L1 = 3-((N-methylimidazolylidenyl)methyl)-5-methylpyrazolate), [Ni3(μ-OH)(L2)3](PF6)2 (2, L2 = 3-((N-mesitylimidazolylidenyl)methyl)-5-methylpyrazolate), and [Ni3(μ-OH)(L3)3](PF6)2 (3, L3 = 3-((N-pyrimidin-2-ylimidazolylidenyl)methyl)-5-methylpyrazolate) were obtained by the reactions of corresponding silver–NHC complexes with Raney nickel powder at

  三种金属漆镍配合物[Ni 3（μ-OH）（L1）3 ]（PF 6）2（1，L1 = 3-（（（N-甲基咪唑基烯基）甲基）-5-甲基吡唑酸酯），[Ni 3（μ-OH ）（L2）3 ] [PF 6）2（2，L2 = 3-（（N-甲酰亚胺基咪唑基烯基甲基）甲基）-5-甲基吡唑酸酯）和[Ni 3（μ-OH）（L3）3 ]（PF 6）2（3，L3 = 3-（（N-嘧啶-2-吡啶并咪唑啉基甲基）-5-甲基吡唑酸酯是通过相应的银-NHC配合物与阮内镍粉在45°C下反应制得的。在80℃下的相同反应得到[Ni 3（L2）4 ]（PF 6）2（4）。的卡宾转移反应的银-卡宾络合物[（η 3 -C 3 H ^ 5）的PdCl] 2，得到heterotrimetallic络合物[银钯2（η 3 -C 3 H ^ 5）2（L2）2 ]（PF 6）（5），而与Pt（cod）Cl 2的卡宾转移反应得到[Pt 2（L3）2
• Geminal-atom catalysis for cross-coupling
  作者：Xiao Hai、Yang Zheng、Qi Yu、Na Guo、Shibo Xi、Xiaoxu Zhao、Sharon Mitchell、Xiaohua Luo、Victor Tulus、Mu Wang、Xiaoyu Sheng、Longbin Ren、Xiangdong Long、Jing Li、Peng He、Huihui Lin、Yige Cui、Xinnan Peng、Jiwei Shi、Jie Wu、Chun Zhang、Ruqiang Zou、Gonzalo Guillén-Gosálbez、Javier Pérez-Ramírez、Ming Joo Koh、Ye Zhu、Jun Li、Jiong Lu

  DOI：10.1038/s41586-023-06529-z

  日期：2023.10.26

  bonding for diverse C–X (X = C, N, O, S) cross-couplings with a low activation barrier. In situ characterization and quantum-theoretical studies show that such a dynamic process for cross-coupling is triggered by the adsorption of two different reactants at geminal metal sites, rendering homo-coupling unfeasible. These intrinsic advantages of GACs enable the assembly of heterocycles with several coordination

  单原子催化剂 (SAC) 具有明确的活性位点，使其在有机合成中具有潜在意义1,2,3,4。然而，由于空间环境和电子量子态的限制，这些稳定在固体载体上的单核金属物质的结构可能不是催化复杂分子转化的最佳选择5,6。在这里，我们报告了一类异质孪生原子催化剂（GAC），它以特​​定的配位和空间接近度配对单原子位点。在聚合氮化碳 (PCN) 主体中，规则分离的具有离域 π 键合性质的氮锚定基团7允许在高金属密度下以约 4 Å 的基态间隔配位铜孪生位点8。GAC 中各个 Cu 位点的适应性协调，通过动态 Cu-Cu 键合，实现了具有低活化势垒的多种 C-X (X = C、N、O、S) 交叉偶联的协作桥偶联途径。原位表征和量子理论研究表明，这种交叉偶联的动态过程是由两种不同反应物在偕金属位点的吸附引发的，使得同质偶联不可行。GAC 的这些内在优势使得能够组装具有多个配位位点的杂环、空间拥挤的支架和具有高
• Per-6-amino-β-cyclodextrin as an Efficient Supramolecular Ligand and Host for Cu(I)-Catalyzed <i>N</i>-Arylation of Imidazole with Aryl Bromides
  作者：Palaniswamy Suresh、Kasi Pitchumani

  DOI：10.1021/jo801811w

  日期：2008.11.21

  Per-6-amino-beta-cyclodextrin (per-6-ABCD), acting simultaneously as a supramolecular ligand for CuI and host for aryl bromides, catalyzes N-arylation of imidazole with aryl bromides under mild conditions. This simple method proceeds with excellent yield for the coupling of imidazole with various substituted aryl bromides demonstrating good tolerance of other functionalities.
• Synthesis, structural characterization and luminescence studies of three novel complexes of asymmetric 5-(1-imidazolyl)pyrimidine ligand
  作者：Gui-Ge Hou、Ju-Feng Sun、Chun-Hua Wang、Feng Zhao、Xian-Ping Dai、Hong-Juan Li、Jing-Tian Han

  DOI：10.1016/j.molstruc.2013.05.065

  日期：2013.9

  Three novel complexes (L)(2)CdI2 (1), (L)(4)Zn(NO3)(2) (2) and (L)(2)Cd(NO3)(2)center dot(CH3CN)(2) (3) were prepared based on asymmetric ligand 5-(1-imidazolyl)pyrimidine (L) with metal salts, respectively. The single-crystal structure reveals that L acts as a monodentate ligand to coordinate a M(II) center to generate a discrete (L)(2)CdI2} in 1 and a tetrahedral [Zn(L)(4)](2+) moiety in 2, respectively. For 3, ligands L as bridging bidentate ligands link two Cd(II) centres to generate a (4, 4) net architecture, further arrange in an -AA- stacking fashion to generate inerratic channels encapsulated guest acetonitrile molecules. In addition, the luminescent properties of L and 1-3 were investigated primarily in the solid state. The structure-property relationship indicates the luminescent property is basically related to its incorporation into the metal-containing complexes, as well as the molecular coplanarity and the intermolecular pi-pi interactions. (c) 2013 Elsevier B.V. All rights reserved.