4-(1-benzyl-1H-1,2,3-triazol-4-yl)benzaldehyde

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-(1-benzyl-1H-1,2,3-triazol-4-yl)benzaldehyde
• 英文别名: 4-(1-Benzyltriazol-4-yl)benzaldehyde；4-(1-benzyltriazol-4-yl)benzaldehyde
• 化学式: C₁₆H₁₃N₃O
• 分子量: 263.299
• InChiKey: QGGKWJXLLZERLW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  47.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  溴甲苯 在 sodium azide 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 68.0h， 生成 4-(1-benzyl-1H-1,2,3-triazol-4-yl)benzaldehyde
  参考文献：
  名称：

  Facile immobilization of copper(I) acetate on silica: A recyclable and reusable heterogeneous catalyst for azide–alkyne clickable cycloaddition reactions

  摘要：

  The structurally well-defined copper(I) acetate was immobilized on silica gel via electrostatic interactions. The catalytic activity of the immobilized catalyst Cu(l)-SiO2 was examined in the click synthesis of 1,2,3-triazoles in water/ethanol at room temperature. The catalyst showed high catalytic activity and regioselectivity for the Huisgen [3+2] cycloaddition reaction between terminal alkynes and azides. The catalyst was recovered by simple filtration and reused for up to five times. The analysis of the local electrophilicity/nucleophilicity has been performed on the dinuclear copper-acetylide complex intermediate. Conceptual DFT (CDFT) analysis enabled the explanation of the formation of 1,2,3-triazole in a regioselective manner. FT-IR, XRPD, SEM and ICP techniques were used to characterize the immobilized catalyst. (C) 2019 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2019.06.030

文献信息

• Organic synthesis via magnetic attraction: benign and sustainable protocols using magnetic nanoferrites
  作者：R. B. Nasir Baig、Rajender S. Varma

  DOI：10.1039/c2gc36455g

  日期：——

  Magnetic nano-catalysts have been prepared using simple modification of iron ferrites. The nm size range of these particles facilitates the catalysis process, as an increased surface area is available for the reaction; the easy separation of the catalysts by an external magnet and their recovery and reuse are additional beneficial attributes. Glutathione bearing nano-ferrites have been used as organocatalysts for the Paal–Knorr reaction and homocoupling of boronic acids. Nanoferrites, post-synthetically modified by ligands, were used to immobilize nanometals (Cu, Pd, Ru, etc.) which enabled the development of efficient, sustainable and green procedures for azide–alkynes-cycloaddition (AAC) reactions, C–S coupling, O-allylation of phenol, Heck-type reactions and hydration of nitriles.

  通过简单修饰铁氧体，已制备出磁性纳米催化剂。这些粒子处于纳米尺寸范围，有助于催化过程，因为反应可利用增加的表面积；外部磁铁易于分离催化剂，并可回收和重复使用，这些是额外的有益特性。负载谷胱甘肽的纳米铁氧体已用作有机催化剂，用于Paal-Knorr反应和硼酸的均偶联。通过配体后合成改性的纳米铁氧体，用于固定纳米金属（铜、钯、钌等），从而实现了高效、可持续和绿色的叠氮-炔烃环加成（AAC）反应、碳-硫偶联、酚的烯丙基化、 Heck型反应和腈的水合反应的方法发展。
• A Highly Active and Magnetically Recoverable Tris(triazolyl)-Cu^ICatalyst for Alkyne-Azide Cycloaddition Reactions
  作者：Dong Wang、Laetitia Etienne、María Echeverria、Sergio Moya、Didier Astruc

  DOI：10.1002/chem.201304536

  日期：2014.4.1

  Nanoparticle‐supported tris(triazolyl)–CuBr, with a diameter of approximately 25 nm measured by TEM spectroscopy, has been easily prepared, and its catalytic activity was evaluated in the copper‐catalyzed azide–alkyne cycloaddition (CuAAC) reaction. In initial experiments, 0.5 mol % loading successfully promoted the CuAAC reaction between benzyl azide and phenylacetylene, in water at room temperature

  纳米颗粒支撑的三（三唑基）-CuBr的制备非常容易，通过TEM光谱法测得的直径约为25 nm，并在铜催化的叠氮化物-炔烃环加成（CuAAC）反应中评估了其催化活性。在最初的实验中，室温下（25°C），0.5 mol％的负载量成功地促进了叠氮化物和苯乙炔之间的CuAAC反应。在此过程中，氧化铁纳米颗粒负载的三（三唑基）-CuBr表现出良好的单分散性，出色的可回收性和出色的可重复使用性。实际上，它是通过使用外部磁体简单地收集并从反应介质中分离出来的，然后用于另外五个催化循环，而不会明显丧失催化活性。第一个循环的电感耦合等离子体（ICP）分析表明，从催化剂浸出到反应介质中的铜量可以忽略不计（1.5 ppm）。通过检查底物的范围，发现该方法可以成功地扩展到各种有机叠氮化物和炔烃，也可以通过涉及苄基溴化物，炔烃和钠的级联反应应用于三唑的一锅法合成叠氮化物。此外，该催化剂被证明是用于合成烯丙基和TEG端基（TEG
• The copper–nicotinamide complex: sustainable applications in coupling and cycloaddition reactions
  作者：R. B. Nasir Baig、Buchi Reddy Vaddula、Mallikarjuna N. Nadagouda、Rajender S. Varma

  DOI：10.1039/c4gc02047b

  日期：——

  The copper(ii)–nicotinamide complex catalyzes the C–S, C–N bond forming and cycloaddition reactions under a variety of sustainable reaction conditions.

  铜（II）-烟酰胺配合物在各种可持续反应条件下催化C-S、C-N键形成和环加成反应。
• Highly Efficient and Stable Atomically Dispersed Cu Catalyst for Azide‐Alkyne Cycloaddition Reaction
  作者：Peng Ren、Qinglin Li、Tao Song、Zhaozhan Wang、Ken Motokura、Yong Yang

  DOI：10.1002/cctc.202100831

  日期：2021.9.17

  In this study, we report a highly stable and efficient single-atom Cu dispersed on N-doped porous carbon as a superior catalyst for azide-alkyne cycloaddition reaction. A broad set of 1,4-disubstituted 1,2,3-triazoles was synthesized in high to excellent yields with good tolerance of various functional groups in a cost-effective, environment-friendly manner. Parallel studies show that the single-atom

  在这项研究中，我们报告了一种分散在 N 掺杂多孔碳上的高度稳定和高效的单原子 Cu 作为叠氮化物-炔烃环加成反应的优良催化剂。以具有成本效益、环境友好的方式以高到优异的收率合成了广泛的 1,4-二取代 1,2,3-三唑，对各种官能团具有良好的耐受性。平行研究表明，具有独特配位结构的单原子铜表现出优于金属铜纳米颗粒类似物的催化活性。值得注意的是，单原子铜催化剂表现出强大的稳定性，可以多次重复使用，而不会改变活性和区域选择性。
• A highly active magnetically recoverable nano ferrite-glutathione-copper (nano-FGT-Cu) catalyst for Huisgen 1,3-dipolar cycloadditions
  作者：R. B. Nasir Baig、Rajender S. Varma

  DOI：10.1039/c2gc16301b

  日期：——

  1,2,3-Triazoles were synthesized in water using magnetically recoverable heterogeneous Cu catalyst via one-pot multi component reaction using MW irradiation. Aqueous reaction medium, easy recovery of the catalyst using an external magnet, efficient recycling, and the high stability of the catalyst renders the protocol economic and sustainable.

  利用磁性可回收的非均相铜催化剂，通过微波辐照下的一锅多组分反应，在水相中合成了1,2,3-三氮唑。水相反应介质、利用外部磁铁轻松回收催化剂、高效循环利用以及催化剂的高稳定性使该方案既经济又可持续。