5-(4-nitrophenyl)-1-phenyl-1H-1,2,3-triazole | 31802-50-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-(4-nitrophenyl)-1-phenyl-1H-1,2,3-triazole
• 英文别名: 5-(4-nitro-phenyl)-1-phenyl-1H-[1,2,3]triazole；1-Phenyl-5-p-nitrophenyl-1,2,3-triazol；5-(4-Nitrophenyl)-1-phenyltriazole
• CAS: 31802-50-3
• 化学式: C₁₄H₁₀N₄O₂
• 分子量: 266.259
• InChiKey: IHDCXXNKZSZMFR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  76.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  叠氮苯 在 palladium diacetate 、 potassium carbonate 、 caesium carbonate 、 copper(II) sulfate 、 sodium ascorbate 、 三(邻甲基苯基)磷 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 44.25h， 生成 5-(4-nitrophenyl)-1-phenyl-1H-1,2,3-triazole
  参考文献：
  名称：

  Pd-Catalyzed Regioselective Arylation on the C-5 Position ofN-Aryl 1,2,3-Triazoles

  摘要：

  We herein report a highly efficient method for the arylation at the C-5 position of N-aryl 1,2,3-triazoles via a direct palladium catalyzed arylation reaction. The optimal reaction conditions required a combination of Pd(OAc)(2) and tris(o-tolyl)phosphine as catalyst, and Cs2CO3 as the base under inert atmosphere. A variety of C-5 substituted N-aryl 1,2,3-triazoles were prepared using these conditions with yields in the 70-88% range. Regioselective C-5 arylations were also performed on 1,4-disubstituted 1,2,3-triazoles. The regioselectivity in triazole substitution at the C-5 position was confirmed by single crystal XRD. In addition, computational investigations of key steps of the catalytic cycle using the density functional theory have provided a rationalization to the selective C-5 arylation of N-aryl 1,2,3-triazoles.

  DOI：

  10.1021/jo5026145

文献信息

• Synthesis of functionalized 1,2,3-triazoles using Bi₂WO₆ nanoparticles as efficient and reusable heterogeneous catalyst in aqueous medium
  作者：Banoth Paplal、Sakkani Nagaraju、Veerabhadraiah Palakollu、Sriram Kanvah、B. Vijaya Kumar、Dhurke Kashinath

  DOI：10.1039/c5ra09544a

  日期：——

  The regioselective synthesis of functionalized triazoles is achieved using a combination of Bi₂WO₆ nanoparticles (10 mol%) and click conditions from β-nitrostyrenes, phenylacetylene and chalcones with azides.

  功能化三唑的区域选择性合成是通过使用Bi₂WO₆纳米颗粒（10 mol％）和β-硝基苯乙烯、苯乙炔和查尔酮与叠氮化物的点击条件相结合实现的。
• Ce(OTf)₃-Catalyzed [3 + 2] Cycloaddition of Azides with Nitroolefins: Regioselective Synthesis of 1,5-Disubstituted 1,2,3-Triazoles
  作者：Ying-Chun Wang、Yu-Yang Xie、Hong-En Qu、Heng-Shan Wang、Ying-Ming Pan、Fu-Ping Huang

  DOI：10.1021/jo5004339

  日期：2014.5.16

  the presence of a catalytic amount of Ce(OTf)3, both benzyl and phenyl azides react with a broad range of aryl nitroolefins containing a range of functionalities selectively producing 1,5-disubstituted 1,2,3-triazoles in good to excellent yields.

  描述了稀土金属催化的有机叠氮化物与硝基烯烃的[3 + 2]环加成反应以及随后的消除反应的第一个实例。在催化量的Ce（OTf）3的存在下，苄基和苯基叠氮化物均与多种芳基硝基烯烃反应，这些芳基硝基烯烃含有一定范围的官能度，可以选择性地制备1,5-二取代的1,2,3-三唑产量。
• Design and applications of new phosphine-free tetradentate Pd-catalyst: Regioselective C–H activation on 1-substituted 1,2,3-triazoles and indoles(NH-Free)
  作者：Sarma V. Markandeya、Ch. Renuka、Parvathi K. Lakshmi、A. Rajesh、Chidara Sridhar、Korupolu Raghu Babu

  DOI：10.1080/00397911.2017.1381260

  日期：2018.1.17

  ABSTRACT This article describes the synthesis of a new phosphine free tetradentate Pd catalyst using dl-2,3-diaminopropionic acid. The complex was characterized by Mass, IR, and 1H NMR. The catalyst is air stable at room temperature and non-hygroscopic. Application of this new catalyst to regioselective C–H activation on 1-substituted 1,2,3-triazole and indoles with aryl iodides to get corresponding

  摘要 本文描述了使用 dl-2,3-二氨基丙酸合成一种新的无膦四齿 Pd 催化剂。该配合物通过质谱、红外和 1 H NMR 表征。该催化剂在室温下对空气稳定且不吸湿。应用这种新催化剂对 1-取代的 1,2,3-三唑和吲哚与芳基碘进行区域选择性 C-H 活化，得到相应的 C-5 和 C-2 芳基化产物，收率令人满意。所有产品均通过光谱研究表征。图形概要
• Regioselective Synthesis of 1,5-Disubstituted 1,2,3-Triazoles by Reusable AlCl₃ Immobilized on <font>γ</font>-Al₂O₃
  作者：Hemmaragala M. Nanjundaswamy、Heidi Abrahamse

  DOI：10.1080/00397911.2014.997366

  日期：2015.4.18

  Abstract There is rapidly growing interest in the synthesis and use of substituted 1,2,3-triazoles. We report an easy and interesting procedure that demonstrates the effectiveness of surface-modified γ-Al2O3, which is reusable, efficient, catalytic, safe, and environmentally acceptable for the regioselective synthesis of 1,5-disubstituted-1,2,3-triazoles via [3 + 2] cycloaddition of phenyl and benzyl

  摘要 人们对取代 1,2,3-三唑的合成和应用的兴趣正在迅速增长。我们报告了一个简单而有趣的过程，它证明了表面改性的 γ-Al2O3 的有效性，它可重复使用、高效、催化、安全且环境可接受，可用于 1,5-二取代-1,2,3-三唑的区域选择性合成通过苯基和苄基叠氮化物与一系列芳基硝基烯烃的 [3 + 2] 环加成反应，收率良好。没有观察到对硝基、氰基、羟基、醚键和卤素等取代基的不利影响。该催化剂很容易回收利用，可重复使用 9 次而不会失去其活性。图形概要
• Novel synthesis of 1,5-disubstituted-1,2,3-triazolines catalysed by Zepto magnetic microspheres under the influence of a rotating magnetic field
  作者：Priyanka Sharma、Srinivasu V. Vallabhapurapu、Wei H. Ho、Nanjundaswamy M. Hemmaragala

  DOI：10.1139/cjc-2018-0349

  日期：2019.3

  The novel reactor has been designed to perform chemical reactions under the influence of a magnetic field generated by alternating magnetic poles as a function of time. The system was successfully employed to synthesize a series of 1,5-disubstituted-1,2,3-triazolines via the regioselective [3 + 2] cycloaddition reactions between alkyl/aryl azides and nitroolefins catalysed by Zepto (para magnetic ultra-blue carboxy functionalized) microspheres (bead diameter 2.5 μm). All of the reactions went smoothly without any adverse effect on nitro, cyano, thienyl, hydroxy, halogens, and ether functions at 25 ± 2 °C and afforded 82%–99% pure products at a magnetic field of 18.99 mT and an exposure time of 180–240 min. The influence of the magnetic force exerted on the magnetic materials was found to enhance the catalytic activity of microspheres. The catalyst could easily be separated by simple centrifugation, which could be reused for at least 15 runs with no loss in activity.

  该新型反应器被设计为在由交替磁极产生的磁场作用下，以时间为函数进行化学反应。该系统成功地用于合成一系列1,5-二取代-1,2,3-三唑啉，通过磁性超蓝色羧基微球（直径为2.5微米）催化的烷基/芳基偶氮化物和硝基烯烃的区域选择性[3+2]环加成反应。所有反应在25±2℃下顺利进行，对硝基、氰基、噻吩基、羟基、卤素和醚功能没有任何负面影响，并在18.99毫特斯拉的磁场和180-240分钟的曝光时间下得到82%-99%的纯品。发现磁性材料所受的磁力影响增强了微球的催化活性。该催化剂可以通过简单的离心分离，并可重复使用至少15次而不失活性。