1,4-bis(1-benzyl-1H-1,2,3-triazol-4-yl)butane | 1394123-55-7

• 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(1-benzyl-1H-1,2,3-triazol-4-yl)butane
• 英文别名: 1-Benzyl-4-[4-(1-benzyltriazol-4-yl)butyl]triazole
• CAS: 1394123-55-7
• 化学式: C₂₂H₂₄N₆
• 分子量: 372.473
• InChiKey: MBBXKXDIRIDIKJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  61.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1,7-辛二炔 、 溴甲苯 在 sodium azide 、 copper(II) ferrite 作用下， 以 水 为溶剂， 反应 9.0h， 以74%的产率得到1,4-bis(1-benzyl-1H-1,2,3-triazol-4-yl)butane
  参考文献：
  名称：

  Magnetically separable CuFe2O4 nano particles catalyzed multicomponent synthesis of 1,4-disubstituted 1,2,3-triazoles in tap water using ‘click chemistry’

  摘要：

  The synthesis of 1,4-disubstituted 1,2,3-triazoles is attempted using magnetically separable and reusable copper ferrite nano particles in a one pot reaction, in tap water. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.06.077

文献信息

• Copper-Catalyzed Azide–Alkyne Cycloaddition (CuAAC) by Functionalized NHC-Based Polynuclear Catalysts: Scope and Mechanistic Insights
  作者：Miguel González-Lainez、Miguel Gallegos、Julen Munarriz、Ramón Azpiroz、Vincenzo Passarelli、M. Victoria Jiménez、Jesús J. Pérez-Torrente

  DOI：10.1021/acs.organomet.2c00246

  日期：2022.8.8

  coordination mode identical to the functionalized NHC ligands. These compounds have been found to exhibit high catalytic activity in the Cu-catalyzed azide–alkyne cycloaddition (CuAAC) reaction. In particular, [Cu2(μ-Br)2(tBuImCH2pyCH2NEt2)]2 efficiently catalyzes the click reaction of a range of azides and alkynes, under an inert atmosphere at room temperature in neat conditions at a very low catalyst loading

  由柔性官能化 NHC 基多齿配体支持的铜 (I) [Cu 2 (μ-Br) 2 ( t BuImCH 2 pyCH 2 L)] n (L = OMe, NEt 2 , NH t Bu) 化合物已在通过相应的咪唑鎓盐与过量的铜粉和 Ag 2 O 反应的一锅法。X 射线衍射分析表明 [Cu 2 (μ-Br) 2 ( t BuImCH 2 pyCH 2 NEt 2 )] n是由双金属[Cu(μ-Br)] 2形成的线性配位聚合物单位由基于二甲基吡啶的 NHC-py-NEt 2配体连接，该配体作为具有 1κ C -2κ 2 N,N'配位模式的异源双位配体。我们建议聚合物在溶液中分解成更紧凑的四核 [Cu 2 (μ-Br) 2 ( t BuImCH 2 pyCH 2 L)] 2化合物，其配位模式与功能化的 NHC 配体相同。已发现这些化合物在 Cu 催化的叠氮化物-炔烃环加成 (CuAAC) 反应中表现出高催化活性。特别是[Cu
• A New Simplified Protocol for Copper(I) Alkyne–Azide Cycloaddition Reactions Using Low Substoichiometric Amounts of Copper(II) Precatalysts in Methanol
  作者：Harry Heaney、Benjamin Buckley、Maria Figueres、Amna Khan

  DOI：10.1055/s-0035-1560526

  日期：——

  Copper(II) carboxylates are reduced efficiently by methanol in the presence of alkynes and form yellow alkynylcopper(I) polymeric precatalysts that are involved with azides, in the absence of added ligands, in the catalytic cycles that result in the formation of 1,4-disubstituted 1,2,3-triazoles.
• Fluorinated Anions Promoted “on Water” Activity of Di- and Tetranuclear Copper(I) Catalysts for Functional Triazole Synthesis
  作者：Sayantani Saha、Mandeep Kaur、Jitendra K. Bera

  DOI：10.1021/acs.organomet.5b00348

  日期：2015.6.22

  A set of di- and tetra-copper(I) compounds [Cu-2((LH)-H-1)(2)][BArF](2) (1) ((LH)-H-1 = bis(5,7-dimethyl-1,8-naphthyridin-2-yl)amine; BArF = [BC6H3(CF3)(2)}(4)]) and [Cu-4(L-1)(2)(L-2)(2)][BNBF](2) (2) (L-2 = 5,7-dimethyl-1,8-naphthyridin-2-amine; BNBF = [NH2B(C6F5)(3)}(2)]), stabilized by naphthyridine-based ligands and containing fluorinated anions, is synthesized. Their catalytic utility for copper(I)-catalyzed azidealkyne coupling (CuAAC) reactions in organic solvents and on water is evaluated. The dimer analogue [Cu-2((LH)-H-1)(2)][BPh4](2) (3) with nonfluorinated anion is synthesized for the purpose of comparison. All three compounds show CuAAC activity in organic solvents, although the performance of 3 is considerably lower. Remarkable rate enhancement is displayed by compounds containing fluorinated anions (1 and 2) under on water conditions for the model reaction involving benzyl azide, affording 98% conversions in 1520 min, where compound 3 gives 76% conversions in 50 min. Kinetic experiments reveal the involvement of two coppers in the cycloaddition process. Employing a host of substrates, the usefulness of fluorinated anions to dramatically improve the catalytic activity of Cu(I) compounds under on water conditions is demonstrated.
• [EN] GROUP 9 TRANSITION METAL CATALYSTS AND PROCESS FOR USE OF SAME<br/>[FR] CATALYSEURS À MÉTAL DE TRANSITION DU GROUPE 9 ET PROCÉDÉ D'UTILISATION DE CEUX-CI
  申请人：GUANG MING INNOVATION COMPANY WUHAN

  公开号：WO2014172885A1

  公开（公告）日：2014-10-30

  This invention relates to group 9 transition metal catalysts and process for use of the catalysts in alkyne-azide cycloaddition (Click reaction), in reaction utilizing CO2 as a carbon feedstock to react with epoxides to produce cyclic or polycarbonate products and in reactions utilizing CO2 as a carbon feedstock to react with terminal alkynes to produce carboxylic acids. The catalyst compounds of the invention are represented by the formula (I) wherein M is a Group 9 metal; X is an anionic ligand; L is a two electron donor ligand bearing two ionic groups (G); and by the formula (II) wherein M is a group 9 metal; L1 and L2 are two-electron donor ligands each bearing one ionic group (G) and A - is anion. The present invention also relates to an easy applicable catalyst synthesis and the application in different click-processes, different reactions involving CO2 and their different application fields. The invention has utility in the fields of catalysis, organic synthesis, polymer chemistry, and industrial and fine chemicals chemistry.