1,4-bis(pyrazol-1-ylmethyl)benzene | 172606-21-2

• 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: 1,4-bis(pyrazol-1-ylmethyl)benzene
• 英文别名: 1,4-bis((1H-pyrazol-1-yl)methyl)benzene；1,4-bis(pyrazolylmethyl)benzene；1,4-Bis[(pyrazole-1-yl)methyl]benzene；1-[[4-(pyrazol-1-ylmethyl)phenyl]methyl]pyrazole
• CAS: 172606-21-2
• 化学式: C₁₄H₁₄N₄
• 分子量: 238.292
• InChiKey: OQRHZXAUNOSHHY-UHFFFAOYSA-N

物化性质

• 沸点：
  446.2±38.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 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：

  silver trifluoromethanesulfonate 、 1,4-bis(pyrazol-1-ylmethyl)benzene 以 水 、 丙酮 为溶剂， 以76%的产率得到
  参考文献：
  名称：

  Self-assembly of three cationic silver(I) coordination networks with flexible bis(pyrazolyl)-based linkers

  摘要：

  Three new cationic silver(I) coordination polymers, {[Ag(mu-bpmb)](SO3CF3)}(n) (1), {[Ag(mu-bdb)(1.5)] (SO3CF3)}(n) (2) and {[Ag(mu-bpb)(2)](NO3)}(n) (3), with flexible 1,4-bisRpyrazolyl)methyl]benzene (bpmb), 1,4-bis[(3,5-dimethylpyrazolyl)methyl]benzene (bdb), and 1,4-bis(pyrazolyl)butane (bpb) have been prepared at room temperature by the solvent layering method. The three compounds were characterized by FT-IR spectroscopy, PXRD, elemental analyses and single-crystal X-ray diffraction. Compound 1 is a highly undulated polymeric 1D chain in which the silver ions adopt a linear geometry, coordinating two bpmb linkers. Compounds 2 and 3 are both 2D coordination polymers with their silver atoms being three and four coordinated, and resulting in 6(3)-hcb and 4(4)-sql underlying net topologies, respectively. The flexible bispyrazolyl ligands display various conformations in the solid state, causing the formation of different Ag...Ag separations in the polymeric structures. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2017.03.048
• 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-bis(pyrazol-1-ylmethyl)benzene
  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 and characterization of new oligomeric and polymeric complexes based on the [CuII(bpca)]+ unit [Hbpca=bis(2-pyridylcarbonyl)amine]
  作者：L. Carlucci、G. Ciani、S. Maggini、D.M. Proserpio、R. Sessoli、F. Totti

  DOI：10.1016/j.ica.2011.07.017

  日期：2011.10

  quite shorter Cu⋯Cu contact of 6.869 A only. We have also obtained a chiral 1D neutral polymeric complex, [Cu3(bpca)2(bipy)3(NO3)4]·6H2O (5), that shows a central linear –Cu–bipy–Cu– chain, with all these Cu atoms connected to two lateral [Cu(bpca)(NO3)2]− groups on two opposite sides by means of bipy spacers. An unprecedented type of Cu(II) neutral trinuclear complex, [Cu3(bpca)2(H2O)2(NO3)2] (6), was

  摘要利用[Cu（bpca）（H2O）2]（NO3）·2H2O（1）结构单元制备了五种基于bpca的新型Cu（II）多核配位化合物[Hbpca =双（2-吡啶基羰基）胺]，并对其进行了表征。通过单晶X射线衍射。我们还分离和表征了起始物种的两种新的晶体形式，它们的水含量较低。新产品中的三个是通过1与不同的刚性或柔性间隔基配体反应获得的双核络合物：[Cu2（bpca）2（H2O）2（bipy）]（NO3）2·6H2O（2）（bipy = 4,4' -Bipyridine）和[Cu2（bpca）2（H2O）2（bpete）]（NO3）2·xH2O（3）[bpete =（E）-1,2-二（吡啶-4-基）乙烷]是线性的哑铃状物种，其Cu⋯Cu间距分别为11.075和13.275A。第三种双核化合物[Cu2（bpca）2（H2O）2（bpx）]（NO3）2·8H2O（4）[bpx = 1,4-双（（1H-吡唑-1-基）甲基）苯]
• Syntheses, structures, and characterizations of three Ag(I) complexes constructed by length-modulated pyrazole-based ligands
  作者：Guang-Feng Hou、Ying-Hui Yu、Xue Wang、Jin-Sheng Gao、Bo Wen、Xiao-Dan Wang、Peng-Fei Yan

  DOI：10.1080/00958972.2013.840774

  日期：2013.10.10

  83}285·10}. Complex 2 has a 3-D framework with a 2-D layer penetrated by an infinite 1-D zigzag chain. Complex 3 exhibits a (4,4)-net racemizing layer structure with nitrate anions filling the cavity. The results indicate that L1 and L2 can adopt varied conformations in formation of the complexes, and the length of the ligands plays a key role in configuring and directing the corresponding structure

  具有 N 供体配体的三种配位配合物 Ag2(L1)1.5(NO3)2 (1)、Ag3(L2)2(NO3)3 (2) 和 Ag(L1)2NO3 (3) L1 = 1,4 -双（吡唑-1-基甲基）苯，L2 = 4,4'-双（吡唑-1-基甲基）联苯}，已通过元素分析、红外光谱、TGA 和 X 射线单晶进行合成和结构表征衍射。复合体 1 显示了一个 3-D fsh-3,4-P21/c 结构，其简码为 83}285·10}。复合体 2 有一个 3-D 框架，其中一个 2-D 层被一个无限的 1-D 之字形链穿透。配合物 3 表现出 (4,4)-净外消旋层结构，其中硝酸根阴离子填充空腔。结果表明，L1和L2在复合物的形成中可以采用不同的构象，配体的长度在配置和指导复合物相应结构中起着关键作用。
• Capture of volatile iodine by newly prepared and characterized non-porous [CuI]_n-based coordination polymers
  作者：Abbas Tarassoli、Valiollah Nobakht、Elham Baladi、Lucia Carlucci、Davide M. Proserpio

  DOI：10.1039/c7ce01193h

  日期：——

  two-dimensional sheets with a 44-sql net. Differently, compound 3 shows a one-dimensional (1D) zigzag chain structure with monomeric CuI units. All the four non-porous coordination polymers show the ability to capture volatile iodine in the gas phase. The solid-state photoluminescence properties of 1a, 1b, and 2 have also been investigated. The iodine-adsorbed samples 1a-I2, 1b-I2, and 2-I2 show no fluorescence

  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
• 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