4-[(4-Pyridin-3-yltriazol-1-yl)methyl]benzonitrile | 1130280-42-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 4-[(4-Pyridin-3-yltriazol-1-yl)methyl]benzonitrile
• CAS: 1130280-42-0
• 化学式: C₁₅H₁₁N₅
• 分子量: 261.286
• InChiKey: DUQVXCUATWNSPY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  67.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-乙炔基吡啶 、 4-(叠氮甲基)苯甲腈 在 铜 作用下， 以 水 为溶剂， 反应 24.0h， 生成 4-[(4-Pyridin-3-yltriazol-1-yl)methyl]benzonitrile
  参考文献：
  名称：

  钴和铜盐的钴茂金属还原及其形成的纳米颗粒的催化行为

  摘要：

  纳米粒子（NPs）的生成方式对于催化，光学，传感和纳米医学中的多种应用非常感兴趣。在此，通过商业钴将快速还原CuSO 4 ·5H 2 O和Ag盐得到的是小，稳定，水溶性的Cu和Ag NP，具有窄的尺寸分布，而没有任何其他配体或载体。银盐抗衡阴离子的变化（NO 3 -，F -，BF 4 - ）强烈地影响以这种方式合成的的AgNPs和加入NaBH的AgNP催化的还原4-硝基苯酚的高表观速率常数的两个等离激元吸收4，表明前体抗衡阴离子与AgNP表面结合。由CuSO 4和钴并茂合成的CuNP是可循环的催化剂，用于水中Cu催化的炔-叠氮化物环加成反应，扩展至各种叠氮化物和炔烃，包括对生物医学感兴趣的化合物进行功能化。CuNP和AgNP的催化活性也是非常有希望的迹象，它们可以进一步扩展到各种其他真正有效的金属NP催化反应中。

  DOI：

  10.1021/acscatal.8b02338

文献信息

• CYCLOADDITION OF AZIDES AND ALKYNES
  申请人：Nolan Steven P.

  公开号：US20090069569A1

  公开（公告）日：2009-03-12

  This invention provides a process which comprises contacting, in a reaction zone, at least one organic azide, at least one alkyne, and at least one N-heterocyclic carbene copper compound in which the ligands are either (i) a halide and an N-heterocyclic carbene or (ii) two N-heterocyclic carbenes and a BF 4 − or PF 6 − anion, to form a 1,2,3-triazole in which at least the 1 and 4 positions each has a substituent. The N-heterocyclic carbene either an imidazol-2-ylidene in which the 1 and the 3 positions each has a substituent which has at least one carbon atom, or a 4,5-dihydro-imidazol-2-ylidene in which the 1 and the 3 positions each has a substituent which has at least one carbon atom.

  这项发明提供了一种方法，其中包括在反应区域中接触至少一种有机叠氮化合物、至少一种炔烃以及至少一种N-杂环卡宾铜化合物，其中配体可以是（i）一种卤素和一种N-杂环卡宾，或者（ii）两种N-杂环卡宾和一个BF4−或PF6−阴离子，以形成一种1,2,3-三唑，其中至少1和4位置各具有一个取代基。N-杂环卡宾可以是1,3位置各具有至少一个碳原子的咪唑-2-基卡宾，或者是1,3位置各具有至少一个碳原子的4,5-二氢咪唑-2-基卡宾。
• Supported NHC-Benzimi@Cu Complex as a Magnetically Separable and Reusable Catalyst for the Multicomponent and Click Synthesis of 1,4-Disubstituted 1,2,3-Triazoles via Huisgen 1,3-Dipolar Cycloaddition
  作者：Arvind Pawar、Shivanand Gajare、Ashutosh Jagdale、Sandip Patil、Wilson Chandane、Gajanan Rashinkar、Suresh Patil

  DOI：10.1007/s10562-021-03772-9

  日期：2022.6

  silica coated copper nano-magnetite NHC-benzimi@Cu complex as heterogeneous catalyst for the multicomponent click reaction via Huisgen 1,3-dipolar cycloaddition reaction of alkyl or aryl halide, sodium azide and terminal alkyne, which affords various1,4-disubstituted 1,2,3-triazoles. The multistep prepared nano catalyst has been characterized by various spectroscopic methods such as FT-IR, TGA, EDX, XRD

  在本文中，我们报道了一种新型磁性可分离二氧化硅包覆的铜纳米磁铁矿 NHC-benzimi@Cu 配合物作为多相催化剂，用于通过烷基或芳基卤化物、叠氮化钠和末端炔烃的 Huisgen 1,3-偶极环加成反应进行多组分点击反应。 ，得到各种1,4-二取代的1,2,3-三唑。多步制备的纳米催化剂已通过多种光谱方法如FT-IR、TGA、EDX、XRD、TEM和VSM进行了表征。涂覆在铜表面的非均相纳米催化剂结构是反应中优异催化剂性能的原因。从环境和经济的角度来看，催化剂的可重复使用性使本协议更加引人入胜。 图形摘要
• Novel Copper Tagged Supported Ionic Liquid Phase Catalyst for the Synthesis of 1,4‑Disubstituted 1,2,3‑Triazoles via Cu-catalyzed Azide–Alkyne Cycloaddition Reactions in Water
  作者：Suraj A. Sonawane、Dattaprasad M. Pore

  DOI：10.1007/s10562-021-03898-w

  日期：2022.11

  was investigated for copper-catalyzed azide-alkyne cycloaddition (CuAAC) of alkyl or aryl halide, sodium azide and terminal alkyne provides a series of 1,4-disubstituted-1,2,3-triazoles in excellent yields. This protocol depicted the advantages such as the use of water as an eco-benign solvent, in situ generations of azides from aryl/alkyl halides, excellent yields, mild reaction conditions, simple workup, shorter

  本手稿探讨了新型抗坏血酸功能化铜标记聚合物负载离子液相催化剂 (PSILPC) 的设计、合成和应用。采用FT-IR、XRD、SEM、TEM、EDS、XPS和ICP-AES等多种物理化学技术对新合成的SILP催化剂进行了表征。研究了合成的 SILP 催化剂对烷基或芳基卤化物、叠氮化钠和末端炔烃的铜催化叠氮化物-炔烃环加成 (CuAAC) 的催化性能，从而提供了一系列 1,4-二取代-1,2,3-三唑优良的产量。该协议描述了诸如使用水作为生态良性溶剂、从芳基/烷基卤化物原位生成叠氮化物、优异的产率、温和的反应条件、简单的后处理、更短的反应时间、高周转次数和高周转频率等优点. 图形概要
• Synthesis of magnetically separable catalyst Cu-ACP-Am-Fe3O4@SiO2 for Huisgen 1,3-dipolar cycloaddition
  作者：S.P. Vibhute、P.M. Mhaldar、S.N. Korade、D.S. Gaikwad、R.V. Shejawal、D.M. Pore

  DOI：10.1016/j.tetlet.2018.08.045

  日期：2018.10

  The present manuscript elicits the use of novel magnetically separable silica coated copper (Cu-ACP-Am-Fe3O4@SiO2) as a heterogeneous nanocatalyst for the Huisgen 1,3-dipolar cycloaddition reaction of alkyl or aryl halide, sodium azide and terminal alkyne, which provide a series of 1,4-disubstituted-1,2,3-triazoles. The catalyst was characterized by various physicochemical techniques such as Powder X-ray Diffraction (XRD), Fourier Transform Infrared Spectroscopy (FT-IR), Scanning Electron Microscopy (SEM), Transmission Electron Microscopy (TEM), Energy Dispersive X-Ray Spectroscopy(EDS), Thermogravimetric analysis (TGA-DSC), X-ray Photoelectron spectroscopy (XPS) and Vibrational sampling magnetometer (VSM). The acquisition of this nanocatalyst is also exemplified by employing reusability test and recycling of synthesized catalyst was achieved multiple times just by sequestering with an external magnet. It is noteworthy that the key-features like mild reaction conditions, simple work-up, High turnover number (TON), high turnover frequency (TOF), no use of hazardous organic solvents, easy recovery and reusability of the catalyst makes the present protocol more fascinating from an environmental and economic point of view. (C) 2018 Elsevier Ltd. All rights reserved.