1-benzyl-4-(4-ethoxyphenyl)-1H-1,2,3-triazole | 1389295-81-1

• 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-benzyl-4-(4-ethoxyphenyl)-1H-1,2,3-triazole
• 英文别名: 1-Benzyl-4-(4-ethoxyphenyl)triazole
• CAS: 1389295-81-1
• 化学式: C₁₇H₁₇N₃O
• 分子量: 279.341
• InChiKey: XIWNSSGKMXNXRY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 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：

  溴甲苯 、 12-((4-methoxyphenyl)ethynyl)-6-phenyl-5,6,7,12-tetrahydrodibenzo[c,f][1,5]azastibocine 在 copper(l) iodide 、 sodium azide 、 4,4'-二甲氧基-2,2'-联吡啶 、 cesium fluoride 作用下， 以 二甲基亚砜 为溶剂， 反应 12.0h， 以78%的产率得到1-benzyl-4-(4-ethoxyphenyl)-1H-1,2,3-triazole
  参考文献：
  名称：

  Cu催化氯锑与末端炔烃交叉偶联得到Sb-炔基锑及其产物转化

  摘要：

  在此，我们描述了一种有效的铜催化末端炔烃与氯锑1a的交叉偶联反应，以合成各种Sb-炔基锑。芳基、烷基和杂芳基乙炔都是可以使用的。该协议显示出良好的功能组耐受性和广泛的底物范围。这些获得的Sb-炔基锑被用作制备1,2,3-三唑的有效偶联配偶体。还提出了催化机制。

  DOI：

  10.1016/j.jorganchem.2022.122352

文献信息

• 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。
• Porous copper catalyzed click reaction in water
  作者：Chen Zhang、Bo Huang、Ying Chen、Dong-Mei Cui

  DOI：10.1039/c3nj00468f

  日期：——

  1,2,3-Triazoles were synthesized in water using a cheaper, simple and easily recyclable heterogeneous porous Cu catalyst via one-pot multi component reaction. The catalyst can be recycled five times without significant loss of its catalytic activity.

  1,2,3-三氮唑在水中通过一种廉价、简单且易于回收的多孔Cu异相催化剂，通过一锅多组分反应合成。该催化剂可以回收五次而不显著降低其催化活性。
• An efficient regioselective copper-catalyzed approach to the synthesis of 1,2,3-triazoles from N-tosylhydrazones and azides
  作者：Zhishuo Zheng、Lei Shi

  DOI：10.1016/j.tetlet.2016.10.033

  日期：2016.11

  An efficient regioselective copper-catalyzed strategy for the synthesis of 1,2,3-triazoles from N-tosylhydrazones and azides has been reported. This transformation opened a new route to synthesize 1,2,3-triazoles which is a common structural motif in natural products and pharmaceuticals. The reactions were smoothly under the optimized conditions and provided the desired product in good yields.

  已经报道了从N-甲苯磺酰hydr和叠氮化物合成1,2,3-三唑的有效的区域选择性铜催化策略。这一转变开辟了一条合成1,2,3-三唑的新途径，这是天然产物和药物中常见的结构基序。在优化的条件下，反应平稳进行，并以良好的收率提供了所需的产物。
• [bmim]PF₆/KOH: A Recyclable Catalytic System for an Azide–Arylacetaldehyde [3 + 2] Cycloaddition
  作者：Yuqin Jiang、Kai Wu、Xuxia Tan、Dandan Zhang、Wenpei Dong、Wei Li、Guiqing Xu、Weiwei Zhang

  DOI：10.3184/174751917x15094552081152

  日期：2017.11

  protocol for the synthesis of 1,4-disubstituted 1,2,3-triazoles from azides and arylacetaldehydes at room temperature was developed using [bmim]PF6/KOH as the reaction medium. It was found that the in situ-generated carbene from [bmim]PF6/KOH acted as the catalyst. In the absence of a transition-metal catalyst and organic solvent, this azide–arylacetaldehyde [3 + 2] cycloaddition proceeds efficiently

  使用 [bmim]PF6/KOH 作为反应介质，开发了一种在室温下由叠氮化物和芳基乙醛合成 1,4-二取代 1,2,3-三唑的快速绿色方案。发现由[bmim]PF6/KOH原位生成的卡宾充当催化剂。在没有过渡金属催化剂和有机溶剂的情况下，这种叠氮化物-芳基乙醛 [3 + 2] 环加成反应高效进行，具有高水平的区域选择性、广泛的底物、优异的产率和温和条件下的简单操作。
• Silver nanoparticles embedded in modified polyallylamine resin as efficient catalysts for alkyne–azide 1,3-dipolar cycloaddition in water
  作者：Xian-Liang Zhao、Ke-Fang Yang、Yan Zhang、Li-Wen Xu、Xiao-Qing Guo

  DOI：10.1016/j.catcom.2015.11.005

  日期：2016.1

  A silver nanoparticle composite based on modified polyallylamine has been synthesized by a simple chemical route and its catalytic activity has been tested for alkyne-azide cycloaddition reaction. This silver nanocomposite shows an excellent catalytic activity at 80 degrees C for the synthesis of 1,4-disubstituted 1,2,3-triazole by alkyne-azide cycloaddition. The solid silver nanocomposite catalyst was characterized by transmission electron microscopy, Fourier-transform infrared spectroscopy, X-ray diffractometry and thermogravimetric analysis. The developed catalyst is stable in air, easy to prepare and can be recovered easily and reused ten times without a significant decrease in activity. (C) 2015 Published by Elsevier B.V.