1-(4-chlorobenzyl)-4-phenyl-1H-1,2,3-triazole | 126800-07-5

• 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-(4-chlorobenzyl)-4-phenyl-1H-1,2,3-triazole
• 英文别名: 1-[(4-chlorophenyl)methyl]-4-phenyltriazole
• CAS: 126800-07-5
• 化学式: C₁₅H₁₂ClN₃
• 分子量: 269.733
• InChiKey: FNURMESTBHGWOM-UHFFFAOYSA-N

物化性质

• 熔点：
  143-144 °C
• 沸点：
  463.5±47.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 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：
  30.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  甲醇 、 1-(4-chlorobenzyl)-4-phenyl-1H-1,2,3-triazole 在 dipotassium peroxodisulfate 、 palladium diacetate 作用下， 反应 12.0h， 以80%的产率得到1-(4-chlorobenzyl)-4-(2,6-dimethoxyphenyl)-1H-1,2,3-triazole
  参考文献：
  名称：

  Palladium-catalyzed selective ortho C–H alkoxylation at 4-aryl of 1, 4-disubstituted 1, 2, 3-triazoles

  摘要：

  The ortho- C H bonds at C(4)-aryl of 1, 4-disubstituted 1, 2, 3-triazoles were regioselectively alkoxylated in good to excellent yields with under the directing of the triazole ring. Some products were found to exhibit strong antifungal capacity to fight against root-rot disease of Panax notoginseng by testing the minimum inhibitory concentration (MIC). (C) 2020 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2020.130985
• 作为产物：
  描述：

  4-chlorobenzyl 4-methylbenzenesulfonate 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 0.11h， 生成 1-(4-chlorobenzyl)-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

• NNN-pincer-copper complex immobilized on magnetic nanoparticles as a powerful hybrid catalyst for aerobic oxidative coupling and cycloaddition reactions in water
  作者：Nasrin Zohreh、Mahboobeh Jahani

  DOI：10.1016/j.molcata.2016.11.007

  日期：2017.1

  such as SEM, TEM, FT-IR, TGA, ICP, XRD, and elemental analysis. The finely engineered supported catalyst is employed in the aerobic oxidative coupling of terminal alkynes and click reaction using only 0.38 and 0.04 mol% catalyst, respectively. All reactions perform under solvent-free condition or green solvent H 2 O. Also, the catalyst is readily recovered and reused for up to 8 and 6 subsequent runs

  摘要 描述了一种简单可靠的方法，用于制备第一个对表面组成具有高度控制的非均相 NNN-钳形铜杂化催化剂。该策略依赖于 2-氨基吡啶与三聚氯氰功能化磁性纳米粒子的共价键合，然后与 CuI 络合。这些声明通过不同的表征方法得到证实，例如 SEM、TEM、FT-IR、TGA、ICP、XRD 和元素分析。精细设计的负载型催化剂用于末端炔烃的有氧氧化偶联和点击反应，分别仅使用 0.38 和 0.04 mol% 的催化剂。所有反应均在无溶剂条件或绿色溶剂 H 2 O 下进行。此外，
• 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 and characterization of active cuprous oxide particles and their catalytic application in 1,2,3‐triazole synthesis via alkyne‐azide cycloaddition reaction in water
  作者：Micky Lanster Sawkmie、Dipankar Paul、Gitumoni Kalita、Khushboo Agarwala、Pradip K. Maji、Paresh Nath Chatterjee

  DOI：10.1002/jhet.3723

  日期：2019.12

  the catalytic prowess of the various cuprous oxide materials in the cycloaddition reaction of alkynes and azides to synthesize 1,4‐disubstituted‐1,2,3‐triazoles. A wide variety of substitutions can nicely be tolerated in our optimized reaction conditions to produce very good to excellent yields of the corresponding triazoles in water at 55 °C. The reactions are carried out in water without any assistance

  活性氧化亚铜材料由CuSO 4 .5H 2合成在各种稳定剂（即十六烷基三甲基溴化铵，十二烷基硫酸钠和聚乙烯吡咯烷酮）存在下，使用亚锡酸钠作为还原剂。合成的氧化亚铜材料通过粉末X射线衍射和傅立叶变换红外光谱法得到了很好的表征，以确定它们的身份，而场发射扫描电子显微镜和能量色散光谱法分别研究了它们的形态和组成。我们已经比较了各种氧化亚铜材料在炔烃和叠氮化物的环加成反应中催化合成1,4-二取代-1,2,3-三唑的催化能力。在我们优化的反应条件下，可以很好地耐受各种各样的取代反应，从而在55°C的水中产生非常好至极好的相应三唑收率。反应在水中进行而无需有机助溶剂或其他添加剂的任何辅助，这使得催化方法既经济又环保。
• An Efficient Three-Component Reaction of Sodium Azide, Haloalkane and Alkyne for the Synthesis of 1, 2, 3-Triazoles Catalyzed by the Bifunctional Ionic Liquid Catalyst Choline Chloride-CuCl in Water
  作者：Xuan-Gan Liu、Xian-Liang Zhao、Yan Zhang、Jian-Rong Gao

  DOI：10.2174/1570178612666150908213423

  日期：2016.2.10

  1, 2, 3-Triazoles were synthesized using a one-pot procedure via a threecomponent reaction between an organic halide, sodium azide and alkyne in the presence of an ionic liquid choline chloride-CuCl catalyst. The catalyst can increase the rate of the nucleophilic substitution reaction and showed a high catalytic activity for the [3+2] Huisgen cycloaddition in water. This method is applicable for a

  在离子液体氯化胆碱-CuCl催化剂存在下，通过一锅法通过有机卤化物，叠氮化钠和炔烃之间的三组分反应合成1、2、3-三唑。该催化剂可提高亲核取代反应的速率，并显示出对水中[3 + 2] Huisgen环加成的高催化活性。该方法适用于多种炔烃，包括芳族和杂环底物。
• CuI nanoparticles on modified poly(styrene-co-maleic anhydride) as an effective catalyst in regioselective synthesis of 1,2,3-triazoles via click reaction: a joint experimental and computational study
  作者：Tahmineh Baie Lashaki、Hossein A. Oskooie、Tayebeh Hosseinnejad、Majid M. Heravi

  DOI：10.1080/00958972.2017.1321742

  日期：2017.6.3

  approaches for different coordination modes. Encouraged by our computational results, this new catalyst was employed in a one-pot, three-component reaction involving terminal alkynes, alkyl halides and sodium azide in water resulting in highly regioselective synthesis of 1,4-disubstituted 1,2,3-triazoles in high to excellent yields. The catalyst was reused without pre-activation and recycled for at least five

  摘要 实现了 CuI 纳米粒子 (NPs) 在改性聚（苯乙烯-共-马来酸酐）[SMA] 上的原位固定。通过扫描电子显微镜 (SEM)、能量色散 X 射线分析 (EDAX) 和电感耦合等离子体 (ICP) 证实了 CuI 在制备的载体上的正确固定。为了定量描述 CuI/SMI 纳米催化剂的实验特征，计算评估了 Cu(I) 离子与改性 SMI 配体在气相和溶液相之间的配位行为和相互作用的性质。在这条线上，通过密度泛函理论（DFT）和分子中原子的量子理论（QTAIM）方法对不同配位模式的电子密度函数的数学性质进行了拓扑计算和分析。受到我们计算结果的鼓舞，这种新催化剂用于一锅三组分反应，包括末端炔烃、卤代烷和叠氮化钠在水中的高度区域选择性合成 1,4-二取代的 1,2,3-三唑，收率很高。催化剂在没有预活化的情况下重复使用并循环使用至少五次，没有观察到其活性的显着降低。