1-(3-methoxybenzyl)-4-phenyl-1H-1,2,3-triazole | 126800-01-9

• 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-(3-methoxybenzyl)-4-phenyl-1H-1,2,3-triazole
• 英文别名: 1-[(3-Methoxyphenyl)methyl]-4-phenyltriazole
• CAS: 126800-01-9
• 化学式: C₁₆H₁₅N₃O
• 分子量: 265.315
• InChiKey: DJJHRHFCGGGJHD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  39.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  间甲氧基苯甲醇 在 sodium azide 、 copper(ll) sulfate pentahydrate 、 potassium carbonate 、 sodium ascorbate 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.19h， 生成 1-(3-methoxybenzyl)-4-phenyl-1H-1,2,3-triazole
  参考文献：
  名称：

  A dicationic, podand-like, ionic liquid water system accelerated copper-catalyzed azide-alkyne click reaction

  摘要：

  In this work, an effective, task specific, dicationic, podand-like ionic liquid was synthesized and applied to improve the capability features of click reaction. Moreover, to broaden the scope and decreasing the serious limitations of preparation methods of organic azides, a simple green procedure for the preparation of alkyl azides, the fundamental starting materials in click reactions, from alcohols under solvent-free conditions and microwave irradiation has been reported, for the first time. (C) 2014 Mohammad Javaherian. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.

  DOI：

  10.1016/j.cclet.2014.09.005

文献信息

• Greener synthesis of 1,2,3-triazoles using a copper(<scp>i</scp>)-exchanged magnetically recoverable β-zeolite as catalyst
  作者：Elizama R. Costa、Floyd C. D. Andrade、Danilo Yano de Albuquerque、Luanne E. M. Ferreira、Thiago M. Lima、Carolina G. S. Lima、Domingos S. A. Silva、Ernesto A. Urquieta-González、Márcio W. Paixão、Ricardo S. Schwab

  DOI：10.1039/d0nj02473b

  日期：——

  Herein, we describe the preparation and thorough characterization of a novel magnetically recoverable copper(I)-exchanged β-zeolite and its use as an efficient catalyst for the synthesis of 1,2,3-triazoles via the one-pot three-component reaction of organic halides, terminal acetylenes, and sodium azide in water. The magnetically recoverable β-zeolite could be easily separated from the reaction mixture

  在这里，我们描述了新型的可磁回收的铜（I）交换的β型沸石的制备和全面表征，以及其作为通过一锅三组分反应合成1,2,3-三唑的有效催化剂的用途水中的有机卤化物，末端乙炔和叠氮化钠。借助磁体可以很容易地从反应混合物中分离出可磁性回收的β沸石，并在几个连续的反应中重复使用。重要的是，一系列表征研究使我们能够揭示催化剂失活的机理，因此提出了一种使其失活的方法。
• Synthesis of a novel resorcin[4]arene–glucose conjugate and its catalysis of the CuAAC reaction for the synthesis of 1,4-disubstituted 1,2,3-triazoles in water
  作者：Ali A. Husain、Kirpal S. Bisht

  DOI：10.1039/c9ra00972h

  日期：——

  transfer catalyst for the CuAAC in water as a green approach for the synthesis of 1,4-disubstituted 1,2,3-triazole species. The catalytic utility of RG (1 mol%) was demonstrated in a multicomponent one-pot CuAAC for various azido/alkyne substrates. The RG acts as a molecular host and a micro-reactor resulting in the 1,4-disubstituted 1,2,3-triazoles in excellent yield.

  报道了使用间苯二酚[4]芳烃糖缀合物 ( RG ) 在水介质中Cu( I ) 催化的叠氮化物-炔烃环加成 (CuAAC) 。构建在间苯二酚[4]芳烃上缘上的八个 β- D-吡喃葡萄糖苷部分提供了一个假糖腔，为水中的水不溶性疏水叠氮基和/或炔烃底物提供了合适的宿主环境。RG的效用被确定为水中 CuAAC 的有效反相转移催化剂，作为合成 1,4-二取代 1,2,3-三唑物质的绿色方法。RG (1 mol%)的催化效用在用于各种叠氮基/炔烃底物的多组分一锅法 CuAAC 中得到证实。RG _作为分子主体和微反应器，以优异的收率生成 1,4-二取代 1,2,3-三唑。
• Azide–alkyne cycloaddition reactions in water <i>via</i> recyclable heterogeneous Cu catalysts: reverse phase silica gel and thermoresponsive hydrogels
  作者：Minkyung Lim、Heejin Lee、Minseok Kang、Woncheol Yoo、Hakjune Rhee

  DOI：10.1039/c8ra00306h

  日期：——

  Functionalized reverse phase silica gel and thermoresponsive hydrogels were synthesized as heterogeneous catalysts supports. Cu(I) and Cu(II) catalysts immobilized onto two types of supports were prepared and characterized. The copper catalyzed azide–alkyne cycloaddition was performed in water via a one-pot reaction and yielded good results. These catalysts are air stable and reusable over multiple

  合成了功能化的反相硅胶和热响应水凝胶作为非均相催化剂载体。制备并表征了固定在两种载体上的Cu( I ) 和 Cu( II ) 催化剂。铜催化的叠氮化物-炔烃环加成反应在水中通过一锅反应进行，并产生了良好的结果。这些催化剂对空气稳定且可多次使用。
• 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。
• CuI/Et2NH-Catalyzed One-Pot Highly Efficient Synthesis of 1,4-Disubstituted 1,2,3-Triazoles in Green Solvent Glycerol
  作者：Yongde Zhao、Shengqiang Guo、Yang Zhou、Bencai Dai、Cuimeng Huo、Changchun Liu

  DOI：10.1055/s-0036-1591557

  日期：2018.6

  temperature. A concise one-pot three-component reaction of organic halides­, terminal acetylenes, and sodium azide provided an efficient route for the synthesis of 1,2,3-triazoles. A variety of 1,2,3-triazoles were prepared in good to excellent yields with green solvent glycerol. This procedure used CuI and diethylamine, which are two easily available reagents as the new catalytic system at room temperature

  摘要 有机卤化物，末端乙炔和叠氮化钠的简明的一锅三组分反应为合成1,2,3-三唑提供了一条有效途径。用绿色溶剂甘油制备了各种1,2,3-三唑，收率良好至优异。该程序使用了CuI和二乙胺，它们是两种容易获得的试剂，在室温下可作为新的催化体系。 有机卤化物，末端乙炔和叠氮化钠的简明的一锅三组分反应为合成1,2,3-三唑提供了一条有效途径。用绿色溶剂甘油制备了各种1,2,3-三唑，收率良好至优异。该程序使用了CuI和二乙胺，它们是两种容易获得的试剂，在室温下可作为新的催化体系。