1-benzyl-5-(2-nitrophenyl)-1H-1,2,3-triazole | 1353714-65-4

• 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-5-(2-nitrophenyl)-1H-1,2,3-triazole
• 英文别名: 1-benzyl-5-(2-nitrophenyl)-1,2,3-triazole；1-Benzyl-5-(2-nitrophenyl)triazole
• CAS: 1353714-65-4
• 化学式: C₁₅H₁₂N₄O₂
• 分子量: 280.286
• InChiKey: AEJUGRDGKOSTTP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  21
• 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：
  76.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  溴甲苯 在 sodium azide 、 AlCl3 on γ-Al2O3 作用下， 以 水 、 丙酮 、 甲苯 为溶剂， 反应 32.0h， 生成 1-benzyl-5-(2-nitrophenyl)-1H-1,2,3-triazole
  参考文献：
  名称：

  γ-Al2O3 上可重复使用的 AlCl3 区域选择性合成 1,5-二取代 1,2,3-三唑

  摘要：

  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

  DOI：

  10.1080/00397911.2014.997366

文献信息

• 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。
• 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。
• Regioselective synthesis of 1,5-disubstituted 1,2,3-triazoles by 1,3-dipolar cycloaddition: Role of Er(OTf)3, ionic liquid and water
  作者：Loredana Maiuolo、Beatrice Russo、Vincenzo Algieri、Monica Nardi、Maria Luisa Di Gioia、Matteo Antonio Tallarida、Antonio De Nino

  DOI：10.1016/j.tetlet.2019.01.053

  日期：2019.2

  A simple procedure to obtain 1,5-disubstituted 1,2,3-triazoles, using the Er(OTf)3/[mpy]OTf/H2O catalytic system is described. The reaction proceeds through an eliminative azide–olefin cycloaddition (EAOC) offering a highly regioselective approach and good yields (81–94%). The advantages of this method include simple operations of work-up and the ability of the catalytic system to be re-used five times

  描述了使用Er（OTf）3 / [mpy] OTf / H 2 O催化体系获得1,5-二取代的1,2,3-三唑的简单程序。该反应通过消除叠氮化物-烯烃环加成反应（EAOC）进行，提供了高度区域选择性的方法和良好的收率（81-94％）。该方法的优点包括后处理的简单操作以及催化体系可以重复使用五次而不会明显降低产率的能力。推测了IL和水的作用，还引起了可能的离子自组装（ISA）效应。
• Synthesis and Computational Analysis of Densely Functionalized Triazoles Using <i>o</i>-Nitrophenylalkynes
  作者：Melissa L. McIntosh、Ryne C. Johnston、Ommidala Pattawong、Bradley O. Ashburn、Michael R. Naffziger、Paul Ha-Yeon Cheong、Rich G. Carter

  DOI：10.1021/jo202467k

  日期：2012.1.20

  Dipolar cylcoadditions with azides using a series of o-nitrophenylethynes and disubstituted alkynes were studied experimentally and computationally. Density functional theory computations reveal the steric and electronic parameters that control the regioselectivity of these cycloadditions. Several new substrates were predicted that would either give enhanced regiocontrol or invert the regiochemical preference. Experimentally, the alkynes were screened in the [3 + 2] cycloaddition with benzyl azide. Of the 11 alkynes screened experimentally, the acetylenes containing halogen substitution directly on the alkyne provided the highest levels of regioselectivity. These haloalkynes were also shown to tolerate variation of the azide moiety with continued good levels of regioselectivity in most cases. Diverse functional groups can be incorporated through the cycloaddition process and their subsequent orthogonal modification was demonstrated.
• A tunable route to oxidative and eliminative [3+2] cycloadditions of organic azides with nitroolefins: CuO nanoparticles catalyzed synthesis of 1,2,3-triazoles under solvent-free condition
  作者：D. Gangaprasad、J. Paul Raj、T. Kiranmye、R. Sasikala、K. Karthikeyan、S. Kutti Rani、J. Elangovan

  DOI：10.1016/j.tetlet.2016.06.004

  日期：2016.7

  A regioselective and tunable synthesis of 1,5-disubstituted 1,2,3-triazloles from oxidative and eliminative [3+2] cycloadditions of nitroolefins and organic azides under solvent-free condition in the presence and absence of commercially available CuO nanoparticle catalyst is described. In the presence of the catalyst under solvent-free condition, nitro group is retained in the product while it gets eliminated in the absence of the catalyst. (C) 2016 Elsevier Ltd. All rights reserved.