1,3-bis(imidazol-1-ylmethyl)-5-methylbenzene | 314288-91-0

• 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: 1,3-bis(imidazol-1-ylmethyl)-5-methylbenzene
• 英文别名: 1-[[3-(imidazol-1-ylmethyl)-5-methylphenyl]methyl]imidazole
• CAS: 314288-91-0
• 化学式: C₁₅H₁₆N₄
• 分子量: 252.319
• InChiKey: LUIMDWRKKORWMD-UHFFFAOYSA-N

物化性质

• 熔点：
  105-106 °C
• 沸点：
  490.4±35.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  35.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,3-bis(imidazol-1-ylmethyl)-5-methylbenzene 、 bis(acetonitrile)palladium(II) bromide 以 二甲基亚砜 为溶剂， 反应 0.5h， 以75%的产率得到Pd2(1,3-bis(imidazol-1-ylmethyl)-5-methylbenzene)₂Br₄
  参考文献：
  名称：

  Distinct structures of inorganic–organic supramolecular assemblies based on discrete metallocyclic complexes incorporating flexible imidazole ligands: Syntheses, crystal structures and properties

  摘要：

  Three new interesting discrete dinuclear metallocyclic complexes, namely, {[Pd-2(1)(4)](NO3)(4)center dot 2DMSO center dot 2H(2)O}(n) (4), [Pd-2(2)(2)Br-4](n) (5), and {[Pd-2(3)(2)Cl-4]center dot 4DMSO}(n) (6) have been successfully synthesized by the reaction of flexible exo-bidentate imidazole-containing ligands 1,3-bis(imidazol-1-ylmethyl)benzene (1),1,3-bis(imidazol-1-ylmethyl)-5-methylbenzene (2), and 2,6-bis(imidazol-1-ylmethyl)-4-tert-butylphenol (3) with corresponding palladium salts. All these complexes were characterized by NMR spectroscopy in combination with elemental analysis, powder X-ray diffraction (PXRD), single-crystal X-ray diffraction, and thermal gravimetric analysis (TGA), respectively. Though all three complexes involve the similar supramolecular building blocks [2+2] metallocyclic units, under the inducement effect of the organic ligands, compounds 4-6 exhibit delicate geometric diversification of the resulting high-dimensional inorganic-organic supramolecular assemblies (e. g., [4+2] lantern-like cage structure, 1D channel, and 2D undulating framework, respectively). Furthermore, these results demonstrate that the secondary interactions such as intermolecular pi center dot center dot center dot pi stacking interactions and hydrogen bonds could play important roles in the aspect of linking low-dimensional entities into high-dimensional supramolecular frameworks. (C) 2013 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.ica.2013.07.014
• 作为产物：
  描述：

  间二甲苯 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 、 sodium hydride 作用下， 以 四氢呋喃 、 四氯化碳 、 mineral oil 为溶剂， 反应 21.0h， 生成 1,3-bis(imidazol-1-ylmethyl)-5-methylbenzene
  参考文献：
  名称：

  Distinct structures of inorganic–organic supramolecular assemblies based on discrete metallocyclic complexes incorporating flexible imidazole ligands: Syntheses, crystal structures and properties

  摘要：

  Three new interesting discrete dinuclear metallocyclic complexes, namely, {[Pd-2(1)(4)](NO3)(4)center dot 2DMSO center dot 2H(2)O}(n) (4), [Pd-2(2)(2)Br-4](n) (5), and {[Pd-2(3)(2)Cl-4]center dot 4DMSO}(n) (6) have been successfully synthesized by the reaction of flexible exo-bidentate imidazole-containing ligands 1,3-bis(imidazol-1-ylmethyl)benzene (1),1,3-bis(imidazol-1-ylmethyl)-5-methylbenzene (2), and 2,6-bis(imidazol-1-ylmethyl)-4-tert-butylphenol (3) with corresponding palladium salts. All these complexes were characterized by NMR spectroscopy in combination with elemental analysis, powder X-ray diffraction (PXRD), single-crystal X-ray diffraction, and thermal gravimetric analysis (TGA), respectively. Though all three complexes involve the similar supramolecular building blocks [2+2] metallocyclic units, under the inducement effect of the organic ligands, compounds 4-6 exhibit delicate geometric diversification of the resulting high-dimensional inorganic-organic supramolecular assemblies (e. g., [4+2] lantern-like cage structure, 1D channel, and 2D undulating framework, respectively). Furthermore, these results demonstrate that the secondary interactions such as intermolecular pi center dot center dot center dot pi stacking interactions and hydrogen bonds could play important roles in the aspect of linking low-dimensional entities into high-dimensional supramolecular frameworks. (C) 2013 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.ica.2013.07.014

文献信息

• Anion exchange properties of a two-dimensional coordination framework of cadmium(II) with 1,3-bis(imidazol-1-ylmethyl)-5-methylbenzeneElectronic supplementary information (ESI) available: solid state IR spectra of the title compound and anion-exchanged product. See http://www.rsc.org/suppdata/nj/b1/b106750h/
  作者：Bin Sui、Jian Fan、Taka-aki Okamura、Wei-Yin Sun、Norikazu Ueyama

  DOI：10.1039/b106750h

  日期：2001.11.1

  A novel 2D coordination polymer, [Cd(dimb)2(MeOH)2](ClO4)2}n where dimb = 1,3-bis(imidazol-1-ylmethyl)-5-methylbenzene, was synthesized by treatment of Cd(ClO4)2·6H2O with the dimb ligand in methanol solution. The complex was characterized by X-ray crystallography; the coordination geometry around Cd(II) is a slightly distorted octahedron with an N4O2 donor set. The results of IR and elemental analysis show that the perchlorate anion can be partially exchanged by the tetrafluoroborate anion and indicate that the framework has anion exchange properties.

  合成了一种新型的二维配位聚合物[Cd(dimb)2(MeOH)2](ClO4)2}n，其中dimb为1,3-双（咪唑-1-基甲基）-5-甲基苯，该聚合物是通过将Cd( )2·6H2O与dimb配体在甲醇溶液中反应制得的。通过X射线晶体学对该复合物进行了表征；Cd(II)周围的配位几何结构为略微扭曲的八面体，具有N4O2配体。红外光谱和元素分析的结果表明，过氯酸根阴离子可以部分被四氟硼酸根阴离子置换，且表明该框架具有阴离子交换的特性。
• Influence of ligand composition on crystal structure formation – isostructurality and morphotropism
  作者：Mihails Arhangelskis、Luc Van Meervelt、Liliana Dobrzańska

  DOI：10.1039/d0ce01302a

  日期：——

  Two new Ag(I) complexes with 1,3-bis(imidazol-1-ylmethyl)benzene (L1) and 1,3-bis(imidazol-1-ylmethyl)-5-methylbenzene (L2), namely [AgL1]CF3SO3}n (1) and [AgL2]CF3SO3}n (2), were synthesised and characterised by SCXRD to uncover the effect that introducing a methyl group to the benzene core of the ligand has on the molecular/crystal structure of the metal complex. The studies revealed a high level

  与1,3-双（咪唑-1-基甲基）苯（L1）和1,3-双（咪唑-1-基甲基）-5-甲基苯（L2）的两个新的Ag（I）配合物，即[Ag L1合成并通过SCXRD表征] CF 3 SO 3 } n（1）和[Ag L2 ] CF 3 SO 3 } n（2），以揭示将甲基引入配体的苯核具有的作用。金属络合物的分子/晶体结构。研究表明所形成的Ag（I）配合物，由一维阳离子链组成，电荷被所施加的抗衡离子中和。这些结果触发了对母体配体的结构研究，正如SCXRD所揭示的，它们在单斜晶系系统的不同空间群中以二水合物的形式结晶。进一步的分析表明，它们分子包装中的基序通常保持不变。但是，在L2中进行了一些形态/位置调整以适应甲基取代基的存在。
• Synthesis, Crystal Structure and Magnetic Behaviour of {[Co(dimb)₂(H₂O)₂]·(NO₃)₂·(H₂O)₂}_n
  作者：Jing-Cai Yao、Li Zhang、Yu-Fang Wang、Lu-Fang Ma、Li-Ya Wang

  DOI：10.1002/zaac.200800103

  日期：2008.8

  The title complex [Co(dimb)2(H2O)2]·(NO3)2·(H2O)2}n (1) (dimb = 1,3-di(imidazol-1-ylmethyl)-5-methylbenzene) has been hydrothermally synthesized by the reaction of dimb with Co(NO3)2·6H2O in aqueous solution. The cobalt(II) atoms are linked by bridging dimb ligands to form 2D corrugated and wavy networks containing Co4(dimb)4 macrocyclic motifs. Two neighboring independent layers interlinked each

  标题络合物[Co (dimb) 2 (H2O) 2] · (NO3) 2 · ( ) 2} n (1) (dimb = 1,3-di (imidazol-1-ylmethyl) -5-methylbenzo)已通过 dimb 与 Co ( ) 2 · 6 在水溶液中反应水热合成。钴 (II) 原子通过桥接 dimb 配体连接，形成包含 Co4 (dimb) 4 大环基序的二维波纹和波浪状网络。两个相邻的独立层以平行方式相互连接，通过O-H...O、N-H...O和C-H...O氢键构建三维结构。磁测量显示与一维链模型在 5–300 K 范围内的弱反铁磁相互作用，J 为 –0.68 cm - 1。
• Self-assembly from metal–organic vesicles to globular networks: metallogel-mediated phenylation of indole with phenyl boronic acid
  作者：Li Yang、Liang Luo、Shuai Zhang、Xiaoyu Su、Jingbo Lan、Chi-Tien Chen、Jingsong You

  DOI：10.1039/c0cc00112k

  日期：——

  Self-assembly of the conformationally flexible bismethylimidazolyl ligands with Pd(OAc)2 is described. Depending on whether the ligands provide the hydrogen bonding donor, a switching of metal–organic vesicles to globular networks gelating solvents is achieved. The metallogels exhibit catalytic activity for the cross-coupling of indole with phenyl boronic acid.

  描述了构象灵活的双甲基咪唑配体与Pd(OAc)2的自组装。根据配体是否提供氢键供体，实现了金属有机囊泡向球状网络凝胶溶剂的转变。这些金属凝胶在吲哚与苯硼酸的交叉耦合反应中表现出催化活性。
• A three-dimensional zinc(II) interpenetrating network and a π–π induced silver(I) zigzag complex connected by 1,3-di(imidazole-1-yl-methyl)-5-methylbenzene
  作者：Yonglin Ma、Wei Huang、Jingcai Yao、Bin Li、Shaohua Gou、Hoong-Kun Fun

  DOI：10.1016/s0022-2860(03)00451-4

  日期：2003.9

  A 3D zinc(II) threefold interpenetrating network [Zn(dimb)(2)](CIO4)(2)}(n) (1) and pi-pi induced silver(I) double zigzag polymer [Ag(dimb)](NO3).(H2O)}(n) (2) were synthesized via a functional bidentate ligand 1,3-di(imidazole-1-yl-methyl)-5-methyl-benzene (dimb). The X-ray single crystal structural study indicated that the former complex represents an example of 3D interpenetrating network with a diamond topology in which aromatic ligands serve as the connector, while the latter is the first double zigzag polymer that has been formed by two adjacent infinite ID zigzags through pi-pi interactions between benzene rings of the ligand. (C) 2003 Elsevier B.V. All rights reserved.