1,1,2,2-tetrakis(1H-pyrazol-1-yl)ethane

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1,1,2,2-tetrakis(1H-pyrazol-1-yl)ethane
• 英文别名: 1,1,2,2-tetra(1H-pyrazol-1-yl)ethane；1,1,2,2-tetrakis(pyrazol-1-yl)ethane；1,1,2,2-Tetra(1H-pyrazol-1-yl)ethane；1-[1,2,2-tri(pyrazol-1-yl)ethyl]pyrazole
• 化学式: C₁₄H₁₄N₈
• 分子量: 294.319
• InChiKey: KEBXPUHLPKEZHM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  71.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,1,2,2-tetrakis(1H-pyrazol-1-yl)ethane 在 硫酸 、 碘 、 碘酸 作用下， 以 溶剂黄146 为溶剂， 反应 6.0h， 以73%的产率得到1,1,2,2-tetrakis(4-iodo-1H-pyrazol-1-yl)ethane
  参考文献：
  名称：

  Synthesis of ditopic ligands containing bis(1H-pyrazol-1-yl)-methane fragments

  摘要：

  New approaches have been proposed for the synthesis of compounds containing two bis(1H-pyrazol-1-yl)methane fragments. Nucleophilic replacement of the halogen atoms in appropriate tetrabromo derivatives by pyrazoles in the superbasic system KOH-DMSO gave ditopic chelating ligands: 1,1,2,2-tetrakis(1H-pyrazol-1-yl)ethane, 1,4-bis[bis(1H-pyrazol-1-yl)methyl]benzene, and 1,4-bis[bis(3,5-dimethyl-1H-pyrazol-1-yl)methyl]benzene. 1,4-Bis[bis(1H-pyrazol-1-yl)methyl]benzene was also synthesized by reaction of 1H-pyrazole with terephthalaldehyde in the presence of thionyl chloride. 1,1,2,2-Tetrakis(1H-pyrazol-1-yl)ethane was converted into the corresponding tetraiodo and tetranitro derivatives.

  DOI：

  10.1134/s1070428007110188
• 作为产物：
  描述：

  吡唑 、 1,1,2,2-四溴乙烷 在 potassium hydroxide 作用下， 以 二甲基亚砜 为溶剂， 反应 6.0h， 以71.4%的产率得到1,1,2,2-tetrakis(1H-pyrazol-1-yl)ethane
  参考文献：
  名称：

  Molecular design and the optimum synthetic route of the compounds with multi-pyrazole and its derivatives and the potential application in antibacterial agents

  摘要：

  Molecular design and efficient synthetic procedures have been developed for pyrazole and its derivatives with different linkers. In particular, twelve compounds with -I or -NO2 substituted groups on the pyrazole ring were synthesized for the first time. These compounds are characterized by element analysis, IR, HNMR, M.P. and X-ray diffraction. In addition, some compounds and corresponding complexes were also assayed in vitro for their ability to inhibit the growth of representative Gram-positive bacteria, Gram-negative bacteria and the fungus. It was worthwhile to note that some compounds could be used as potential antibacterial agents. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2015.06.020

文献信息

• Dinuclear Tetrapyrazolyl Palladium Complexes Exhibiting Facile Tandem Transfer Hydrogenation/Suzuki Coupling Reaction of Fluoroarylketone
  作者：Niranjan Dehury、Niladri Maity、Suman Kumar Tripathy、Jean-Marie Basset、Srikanta Patra

  DOI：10.1021/acscatal.6b01421

  日期：2016.8.5

  fluoroarylketone: tetrapyrazolyl dipalladium complexes with varying Pd–Pd distances efficiently catalyze the tandem reaction involving transfer hydrogenation of fluoroarylketone to the corresponding alcohol and Suzuki–Miyaura cross-coupling reaction of the resulting fluoroarylalcohol under moderate reaction conditions, to biaryl alcohol. The complex with the shortest Pd–Pd distance exhibits the highest tandem

  本文中，我们报告了一个基于双核吡唑基的Pd配合物对氟代芳基酮进行串联催化的例子：具有不同Pd-Pd距离的四吡唑基二钯配合物有效地催化了串联反应，该反应涉及将氟代芳基酮氢化转移至相应的醇和Suzuki-Miyaura交叉偶联在适中的反应条件下将所得的氟代芳基醇反应成联芳基醇。Pd–Pd距离最短的配合物在其双金属类似物中表现出最高的串联活性，就活性和选择性而言，它超过了类似的单核化合物。该反应的动力学清楚地表明，卤代芳基酮还原成卤代醇是串联反应中决定速率的步骤。有趣的是，当氟代芳基酮经历多步串联催化时，氯代和溴代芳基酮仅经历单步CC偶联反应，最终生成联芳基酮。与基于吡唑的Pd化合物不同，前驱体PdCl2和膦基相关配合物（PPh 3）2 PdCl 2和（PPh 3）4 Pd不能表现出串联催化作用。
• Synthesis, crystal structure and electrocatalytic activity of discrete and polymeric copper(II) complexes with bitopic bis(pyrazol-1-yl)methane ligands
  作者：Andrei S. Potapov、Eugenia A. Nudnova、Andrei I. Khlebnikov、Vladimir D. Ogorodnikov、Tatiana V. Petrenko

  DOI：10.1016/j.inoche.2015.01.024

  日期：2015.3

  bitopic bis(pyrazol-1-yl)methane ligands, namely 1,1,2,2-tetrakis(pyrazol-1-yl)ethane, 1,4-bis[bis(pyrazol-1-yl)methyl]benzene and 1,4-bis[bis(3,5-dimethylpyrazol-1-yl)methyl]benzene were prepared. Reactions of ligands with Cu2 + ions in 1:2 ratio gave discrete homodinuclear complexes, while 1:1 ligand-to-metal ratio lead to the formation of coordination polymers. Electrocatalytic activity of compounds

  摘要 含有双位双(吡唑-1-基)甲烷配体的新型配位铜(II)化合物，即1,1,2,2-四(吡唑-1-基)乙烷、1,4-双[双(吡唑-制备了1-基)甲基]苯和1,4-双[双(3,5-二甲基吡唑-1-基)甲基]苯。配体与 Cu2 + 离子以 1:2 的比例反应产生离散的同双核配合物，而 1:1 的配体与金属比例导致配位聚合物的形成。评价了化合物在改性碳糊电极表面氧电还原反应中的电催化活性。
• Synthesis of new polydentate pyrazolyl-ethene ligands by interaction of 1H-pyrazole and 1,1,2,2-tetrabromoethane in a superbasic medium
  作者：Andrei S. Potapov、Evgenia A. Nudnova、Andrei I. Khlebnikov、Vladimir D. Ogorodnikov、Tatiana V. Petrenko

  DOI：10.1002/jhet.566

  日期：2011.5

  Reaction of pyrazole and 1,1,2,2‐tetrabromoethane in a superbasic medium dimethylsulfoxide‐potassium hydroxide was investigated, and a number of pyrazolyl‐ and bromo‐substituted ethenes, which are the products of concurrent substitution and elimination reactions, were identified. Carrying out the reaction using different reagent mole ratios allowed to selectively isolate Z‐1,2‐bis(pyrazol‐1‐yl)ethene

  研究了吡唑与1,1,2,2-四溴乙烷在超碱性介质二甲亚砜-氢氧化钾中的反应，并鉴定了同时进行取代和消除反应的吡唑基和溴取代乙烯。使用不同的试剂摩尔比进行反应，可以选择性地分离Z 1,2-双（吡唑-1-基）乙烯，1,1,2-三（吡唑-1-基）乙烷和1,1， 2,2-四（吡唑-1-基）乙烷。使用X射线衍射法建立了 Z -1，2-双（吡唑-1-基）乙烯}二氯锌的晶体结构。J.杂环化​​学。（2011）。
• Molecular design and the optimum synthetic route of the compounds with multi-pyrazole and its derivatives and the potential application in antibacterial agents
  作者：Ji-Xiao Wang、Zi-Ran Zhu、Feng-Ying Bai、Xin-Yu Wang、Xiao-Xi Zhang、Yong-Heng Xing

  DOI：10.1016/j.poly.2015.06.020

  日期：2015.10

  Molecular design and efficient synthetic procedures have been developed for pyrazole and its derivatives with different linkers. In particular, twelve compounds with -I or -NO2 substituted groups on the pyrazole ring were synthesized for the first time. These compounds are characterized by element analysis, IR, HNMR, M.P. and X-ray diffraction. In addition, some compounds and corresponding complexes were also assayed in vitro for their ability to inhibit the growth of representative Gram-positive bacteria, Gram-negative bacteria and the fungus. It was worthwhile to note that some compounds could be used as potential antibacterial agents. (C) 2015 Elsevier Ltd. All rights reserved.
• Synthesis of ditopic ligands containing bis(1H-pyrazol-1-yl)-methane fragments
  作者：E. A. Nudnova、A. S. Potapov、A. I. Khlebnikov、V. D. Ogorodnikov

  DOI：10.1134/s1070428007110188

  日期：2007.11

  New approaches have been proposed for the synthesis of compounds containing two bis(1H-pyrazol-1-yl)methane fragments. Nucleophilic replacement of the halogen atoms in appropriate tetrabromo derivatives by pyrazoles in the superbasic system KOH-DMSO gave ditopic chelating ligands: 1,1,2,2-tetrakis(1H-pyrazol-1-yl)ethane, 1,4-bis[bis(1H-pyrazol-1-yl)methyl]benzene, and 1,4-bis[bis(3,5-dimethyl-1H-pyrazol-1-yl)methyl]benzene. 1,4-Bis[bis(1H-pyrazol-1-yl)methyl]benzene was also synthesized by reaction of 1H-pyrazole with terephthalaldehyde in the presence of thionyl chloride. 1,1,2,2-Tetrakis(1H-pyrazol-1-yl)ethane was converted into the corresponding tetraiodo and tetranitro derivatives.