1,4-双((3,5-二甲基-1H-吡唑-1-基)甲基)苯 | 172606-22-3

• 物质功能分类: 有机原料 - 杂环化合物
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1,4-双((3,5-二甲基-1H-吡唑-1-基)甲基)苯
• 英文名称: 1,4-bis(3,5-dimethylpyrazol-1-ylmethyl)benzene
• 英文别名: 1,4-bis((3,5-dimethyl-1H-pyrazol-1-yl)methyl)benzene；1-[[4-[(3,5-dimethylpyrazol-1-yl)methyl]phenyl]methyl]-3,5-dimethylpyrazole
• CAS: 172606-22-3
• 化学式: C₁₈H₂₂N₄
• 分子量: 294.399
• InChiKey: WFBNAEBBFHASFJ-UHFFFAOYSA-N

物化性质

• 熔点：
  95-97 °C
• 沸点：
  475.0±45.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  35.6
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险性防范说明：
  P261,P280,P301+P312,P302+P352,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  copper(l) iodide 、 1,4-双((3,5-二甲基-1H-吡唑-1-基)甲基)苯 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 以92%的产率得到[CuI(μ-1,4-bis[(3,5-dimethylpyrazolyl)methyl]benzene)]_n
  参考文献：
  名称：

  通过新制备和表征的无孔[CuI] n基配位聚合物捕获挥发性碘

  摘要：

  四个新的非多孔的CuI-配位聚合物[铜2（μ 3 -I）2（μ-BPB）] Ñ（1A），[Cu（上μ 2 -I）（μ-BPB）] Ñ（1B），[的Cu 4（μ 2 -I）4（μ-BPMB）4 ] ñ（2）和[碘化亚铜（μ-BDB）] ñ（3）（bpb = 1,4-双（吡唑基）丁烷; bpmb = 1,4-双[（吡唑基）甲基]苯; bdb = 1,4-双[（3,5-二甲基吡唑基）甲基]苯）成功制备了它们的结构，并通过单晶X射线衍射，FT-IR光谱，PXRD和元素分析充分表征了它们的结构。晶体学研究表明1a，1b和2表现出二维（2D）结构。在1a中，平行的[Cu 2 I 2 ] n楼梯图案通过bpb接头以完全延伸的构象交联成二维薄片，而在1b和2 Cu 2 I 2的结构中菱形二聚体分别通过bpb和pbmb配体连接成带有4 4 -sql网络的二维薄片。不同地，化合物3显示具有单体CuI单元的一维

  DOI：

  10.1039/c7ce01193h
• 作为产物：
  描述：

  对二甲苯 在 溴 、 potassium hydroxide 作用下， 以 二甲基亚砜 为溶剂， 反应 6.0h， 生成 1,4-双((3,5-二甲基-1H-吡唑-1-基)甲基)苯
  参考文献：
  名称：

  Synthesis, structural, and biological evaluation of the arene-linked pyrazolyl methane ligands and their d9/d10 metal complexes

  摘要：

  A series of the p-bis[(1-pyrazolyl)methyl] benzene ligands (L-1-L-6) in the DMSO system were synthesized. In the mean time, by using the ligands as a linker, a new family of transition metal coordination polymers, namely, [Cu-2(L-1)(2)Cl-4] (1), [Cu-2(L-2)(2)Cl-4] (2), [Ag(L-2)(NO3)] (3). [Zn-2(L-2)(2)(SCN)(4)] (4) and [Cd-2(L-2)(SCN)(4)] (5) [L-1 = 1,4-bis((1H-pyrazol-1-yl)methyl)benzene; L-2 = 1,4-bis(3,5-dimethyl-1H-pyrazol-1-yl)methyl)benzene] have been constructed by the reaction of the p-bis[(1-pyrazolyl)methyl]benzene and corresponding to the transition metal compounds in a mixed solution of CH3OH/C2H5OH at mild temperature condition. All the coordination polymers and p-bis[(1-pyrazolyl)methyl]benzene ligands were characterized by elemental analysis, IR spectroscopy, H-1 NMR and C-13 NMR, and some of them were characterized by UV spectroscopy, thermogravimetric analysis, X-ray powder and X-ray single-crystal diffraction. Structural analyses reveal that the ligands L-3-L-5 (L-3 = 1,4-bis((4-iodo-1H-pyrazol-1-yl)methyl)benzene, L-4 = 1,4-bis((4-iodo-3,5-dimethyl-1H-pyrazol-1-yl)methyl)benzene, L-5 = 1,4-bis((4-nitro-1H-pyrazol-1-yl)methyl) benzene,L-6 = 1,4-bis((4-nitro-3,5-dimethyl-1H-pyrazol-1-yl) methyl) benzene) are discrete organic compound molecules and the complexes 1-5 are 1D M-L-M coordination polymers, which are further interlinked via hydrogen bonds resulting in 2D or even 3D supermolecular networks. The luminescent properties of the coordination polymers 3,4 and 5 were examined by luminescence spectra. The analytic results indicate that different metal complexes with the same ligand have different influence on the characteristic photoluminescence. Furthermore, the cytotoxicity of the ligands L-1-L-6 and complexes 1-5 were evaluated against hepG2 cells. For the ligands of L-1-L-6, the different substituents of the pyrazole ring slightly influenced the cytotoxicity of the cell. It is found that nitro-compounds have shown the highest cytotoxicity under the same concentration condition. The cytotoxic activity of the complexes 1-5 are strongly increased by the introduction of the transition metals. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2012.08.016

文献信息

• Poly(pyrazol-1-ylmethyl)Benzenes: New Multidentate Ligands
  作者：CM Hartshorn、PJ Steel

  DOI：10.1071/ch9951587

  日期：——

  Twelve new multidentate poly(pyrazol-1-ylmethyl)benzene ligands , (5)-(16), have been synthesized by phase-transfer-catalysed alkylations of pyrazoles with poly( bromomethyl )benzenes, and their 1H and 13C n.m.r. spectra have been fully assigned. X-Ray crystal structure determinations have been carried out on the tetrachloropalladate salt of the diprotonated form of 1,4-bis(3,5-dimethylpyrazol-1-ylmethyl)-2,3,5,6-tetramethylbenzene and on hexakis (pyrazol-1-ylmethyl)benzene.

  通过吡唑与聚(溴甲基)苯的相转移催化烷基化反应，合成了十二种新的多齿聚(吡唑-1-基甲基)苯配体(5)-(16)，并完全分配了它们的 1H 和 13C n.m.r. 光谱。对 1,4-双（3,5-二甲基吡唑-1-基甲基）-2,3,5,6-四甲基苯的二质子化形式的四氯钯盐和六(吡唑-1-基甲基)苯进行了 X 射线晶体结构测定。
• Synthesis, crystal structures and photocatalytic properties of four silver(I) coordination polymers based on semirigid bis(pyrazole) and carboxylic acid co-ligands
  作者：Dian-Heng Huan、Yan-Qin Zhao、Gui-Ying Dong、Fu-Jun Yin、Sheng-Chun Wang

  DOI：10.1007/s11243-016-0071-2

  日期：2016.9

  Abstract Four Ag(I) coordination polymers, formulated as [Ag(L1)(tpa)0.5]n (1), [Ag(L2)(ndc)0.5]·0.5H2ndc}n (2), [Ag(L3)0.5(ndc)0.5]n (3) and [Ag(L3)]·H3bptc}n (4) (L1 = 4,4′-bis(pyrazole-1-ylmethyl)-biphenyl, L2 = 4,4′-bis(3,5-dimethylpyrazol-1-ylmethyl)-biphenyl, L3 = 1,4-bis(3,5-dimethylpyrazol-1-ylmethyl)benzene, H2tpa = terephthalic acid, H2ndc = 2,6-naphthalenedicarboxylic acid, H4bptc = 3

  摘要 四种 Ag(I) 配位聚合物，公式为 [Ag(L1)(tpa)0.5]n (1), [Ag(L2)(ndc)0.5]·0.5H2ndc}n (2), [Ag(L3) )0.5(ndc)0.5]n (3) 和 [Ag(L3)]·H3bptc}n (4) (L1 = 4,4'-双(吡唑-1-基甲基)-联苯，L2 = 4,4 '-双(3,5-二甲基吡唑-1-基甲基)-联苯，L3 = 1,4-双(3,5-二甲基吡唑-1-基甲基)苯，H2tpa = 对苯二甲酸，H2ndc = 2,6-萘二甲酸, H4bptc = 3,3',4,4'-联苯四甲酸），已被水热合成和结构表征。复合体 1 具有罕见的双节点 (4,4) 连接 2D 4,4L10 拓扑网络，点符号为 32·4.62·7}232·62·72}。配合物2具有折叠梯状链结构，通过O-H···O氢键和π···π堆积相互作用进一步扩展为3D超分子网络。配合物
• Three Cationic, Nonporous Cu^I-Coordination Polymers: Structural Investigation and Vapor Iodine Capture
  作者：Elham Baladi、Valiollah Nobakht、Abbas Tarassoli、Davide M. Proserpio、Lucia Carlucci

  DOI：10.1021/acs.cgd.8b01446

  日期：2018.11.7

  Three cationic nonporous copper(I) coordination polymers containing bis-pyrazolyl flexible ligands have been prepared and characterized, namely, [Cu(μ-bdb)1.5](PF6)}n (1), [Cu(μ-bpb)2](PF6)}n (2), and [Cu(μ-bpmb)2](PF6)}n (3) (bdb = 1,4-bis(3,5-dimethylpyrazolyl) methyl)benzene; bpb = 1,4-bis(pyrazolyl)butane; bpmb = 1,4-bis(pyrazolyl)methyl)benzene). All compounds were characterized by infrared

  制备并表征了三种含双吡唑基柔性配体的阳离子无孔铜（I）配位聚合物，即[Cu（μ-bdb）1.5 ]（PF 6）} n（1），[Cu（μ-bpb ）2 ]（PF 6）} n（2）和[Cu（μ-bpmb）2 ]（PF 6）} n（3）（bdb = 1,4-双（3,5-二甲基吡唑基）甲基）苯; bpb = 1,4-双（吡唑基）丁烷; bpmb ＝ 1，4-双（吡唑基）甲基）苯）。所有化合物均通过红外，粉末X射线衍射，元素和热分析以及单晶X射线衍射进行表征。化合物1具有甲基取代的吡唑基配体的分子，形成交替的环和带链，其中铜（I）中心在扭曲的三角平面几何结构中是三个配位的。在化合物2和3的铜（I）原子采取扭曲的四面体几何形状赋予二维片材结构具有4 4 - SQL拓扑。有趣的是，碘吸附实验表明2和3的无色晶体在存在碘蒸气的情况下保持不变，而三配位化合物1立即吸收碘并变黑。化合物1和2的阴离子交换行为
• Tandem ethylene oligomerisation and Friedel–Crafts alkylation of toluene catalysed by bis-(3,5-dimethylpyrazol-1-ylmethyl)benzene nickel(ii) complexes and ethylaluminium dichloride
  作者：Asheena Budhai、Bernard Omondi、Stephen O. Ojwach、Collins Obuah、Emmanuel Y. Osei-Twum、James Darkwa

  DOI：10.1039/c3cy00334e

  日期：——

  Three ligands, 1,2-bis(3,5-dimethylpyrazol-1-ylmethyl)benzene (L1), 1,3-bis(3,5-dimethylpyrazol-1-ylmethyl)benzene (L2) and 1,4-bis(3,5-dimethylpyrazol-1-ylmethyl)benzene (L3), were reacted with either nickel(II) chloride or nickel(II) bromide to produce four nickel complexes, Ni(L1)Br2 (1), Ni(L1)Cl2 (2), Ni(L2)Br2 (3), and Ni(L1)Br2 (4). The complexes were either mononuclear, 1 and 2, or polymeric

  三种配体，1,2-双（3,5-二甲基吡唑-1-基甲基）苯（L1），1,3-双（3,5-二甲基吡唑-1-基甲基）苯（L2）和1,4-双（3,5-二甲基吡唑-1-基甲基）苯（L3）与以下任何一种反应镍（II），氯化 或者 溴化镍（II）产生四个镍配合物，Ni（L1）Br 2（1），Ni（L1）Cl 2（2），Ni（L2）Br 2（3）和Ni（L1）Br 2（4）。取决于配体中苯连接基上吡唑基单元的位置，复合物可以是单核的1和2，也可以是聚合的3和4。这是从的晶体结构建立1，2和3。激活后所有四个复合物乙基氯化铝 产生了串联催化剂体系，该体系将乙烯低聚为主要成分 1-丁烯 和 1-己烯然后使用存在于反应介质中的烯烃将甲苯烷基化，该甲苯在反应中用作溶剂。这导致单，二和三烷基甲苯与乙烯，丁烯 和 己烯。
• Poly(pyrazol-1-ylmethyl)benzene Palladium Complexes: Synthesis, Characterisation and Evaluation as Heck Coupling Catalysts
  作者：Nthabiseng M. Motsoane、Ilia A. Guzei、James Darkwa

  DOI：10.1515/znb-2007-0304

  日期：2007.3.1

  The poly(pyrazol-1-ylmethyl)benzenes L1 - L5 react with [PdCl₂(NCMe)₂] or [PdClMe(COD)] to form dinuclear palladium complexes [PdClX(3,5-Me₂pzCH₂)₂-1,2-C₆H₄}₂] (X = Cl (1), Me (2)), [PdCl₂(3,5-Me₂pzCH₂)2-1,3-C₆H₄}₂] (3), palladium complexes [Pd₂(μ-Cl)₂Me₂(3,5- Me₂pzCH₂)₂-1,3-C₆H₄}] (4), [Pd₂(μ-Cl)₂X₂(3,5-Me₂pzCH₂)₂-1,4-C₆H₄}] (X = Cl (5), Me (6)), [Pd₂(μ-Cl)₂Cl₂(3,5-^tBu₂pzCH₂)₂-1,4-C₆H₄}] (7), and tetranuclear [Pd₂(μ-Cl)₂Cl₂(3,5- Me₂pzCH₂)₂}₂-1,4-C₆H₄] (8). The structures of 1, 2 and 8 were confirmed by X-ray structure analysis. The complexes efficiently catalyse the coupling reaction of iodobenzene and butylacrylate at 80 °C.

  聚(pyrazol-1-甲基)苯L1-L5与[PdCl₂(NCMe)₂]或[PdClMe(COD)]反应，形成二核钯配合物[ PdClX(3,5-Me₂pzCH₂)₂-1,2-C₆H₄}₂] (X = Cl (1), Me (2)), [PdCl₂(3,5-Me₂pzCH₂)2-1,3-C₆H₄}₂] (3), 钯配合物 [Pd₂(μ-Cl)₂Me₂(3,5-Me₂pzCH₂)₂-1,3-C₆H₄}] (4), [Pd₂(μ-Cl)₂X₂(3,5-Me₂pzCH₂)₂-1,4-C₆H₄}] (X = Cl (5), Me (6)), [Pd₂(μ-Cl)₂Cl₂(3,5-^tBu₂pzCH₂)₂-1,4-C₆H₄}] (7), 和四核[Pd₂(μ-Cl)₂Cl₂(3,5-Me₂pzCH₂)₂}₂-1,4-C₆H₄] (8)。1、2和8的结构经过X射线结构分析证实。这些配合物能有效催化碘苯和丁基丙烯酸酯的偶联反应，在80℃下进行。