1-benzyl-4-(2-nitrophenyl)-1H-1,2,3-triazole | 1158998-66-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-benzyl-4-(2-nitrophenyl)-1H-1,2,3-triazole
• 英文别名: 1-Benzyl-4-(2-nitrophenyl)triazole；1-benzyl-4-(2-nitrophenyl)triazole
• CAS: 1158998-66-3
• 化学式: C₁₅H₁₂N₄O₂
• 分子量: 280.286
• InChiKey: DGCQPXQEYQBUGK-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：

  1-溴-2-硝基苯 在 吡啶 、 copper(l) iodide 、 四(三苯基膦)钯 、 sodium azide 、 potassium carbonate 、 copper(II) sulfate 、 三乙胺 、 维生素 C 作用下， 以 甲醇 、 水 为溶剂， 反应 24.0h， 生成 1-benzyl-4-(2-nitrophenyl)-1H-1,2,3-triazole
  参考文献：
  名称：

  One-Pot Click Synthesis of 1N-Alkyl-4-aryl-1,2,3-triazoles from Protected Arylalkynes and Alkyl Bromides

  摘要：

  通过对应(芳基乙炔基)三甲基硅烷和烷基溴的多组分一锅法方案，已制备了1N-烷基-4-芳基-1,2,3-三唑类化合物。原位形成烷基叠氮化物和炔基去保护，然后通过铜(I)催化的点击环加成反应，通常以良好至优异的产率获得了所需的1,4-二取代-1,2,3-三唑，观察到的不期望的1,5-位异构环加成物仅有微量。该方案消除了对活性有机叠氮化物和末端炔烃的需求。

  DOI：

  10.1055/s-0030-1260256

文献信息

• Phosphoramidite accelerated copper(i)-catalyzed [3 + 2] cycloadditions of azides and alkynes
  作者：Lachlan S. Campbell-Verduyn、Leila Mirfeizi、Rudi A. Dierckx、Philip H. Elsinga、Ben L. Feringa

  DOI：10.1039/b822994e

  日期：——

  Monodentate phosphoramidite ligands are used to accelerate the copper(i)-catalyzed 1,3-dipolar cycloaddition of azides and alkynes (CuAAC) rapidly yielding a wide variety of functionalized 1,4-disubstituted-1,2,3-triazoles; Cu(i) and Cu(ii) salts both function as the copper source in aqueous solution to provide excellent yields.

  单齿亚磷酰胺配体可用于加速铜（i）催化的叠氮化物和炔烃（CuAAC）的1,3-偶极环加成反应，从而迅速生成各种官能化的1,4-二取代-1,2,3-三唑。Cu（i）和Cu（ii）盐均充当水溶液中的铜源，以提供优异的收率。
• Azide-Alkyne Cycloaddition (CuAAC) in Alkane Solvents Catalyzed by Fluorinated NHC Copper(I) Complex
  作者：Maxim A. Topchiy、Alexandra A. Ageshina、Pavel S. Gribanov、Salekh M. Masoud、Timur R. Akmalov、Sergey E. Nefedov、Sergey N. Osipov、Mikhail S. Nechaev、Andrey F. Asachenko

  DOI：10.1002/ejoc.201801538

  日期：2019.2.7

  A highly efficient and environmentally benign protocol for copper‐catalyzed alkyne–azide cycloaddition (CuAAC) in industrially important alkane solvents was developed. New (NHCF)CuI complex decorated with bulky group [(CF3)2(OiAm)C–] exhibited the best catalytic activity in the reactions of diversely substituted alkyne and azide substrates in alkane solvents.

  针对工业上重要的烷烃溶剂中的铜催化的炔-叠氮化物环加成（CuAAC），开发了一种高效且对环境无害的方案。新的（NHC F）Cu I络合物装饰有大体积基团[（CF 3）2（O i Am）C–]在烷烃溶剂中不同取代的炔烃和叠氮化物底物的反应中表现出最佳的催化活性。
• Polymer anchored ruthenium complex: A highly active and recyclable catalyst for one-pot azide–alkyne cycloaddition and transfer-hydrogenation of ketones under mild conditions
  作者：Rostam Ali Molla、Anupam Singha Roy、Kajari Ghosh、Noor Salam、Md Asif Iqubal、K. Tuhina、Sk Manirul Islam

  DOI：10.1016/j.jorganchem.2014.11.007

  日期：2015.1

  catalyst. Aromatic ketones have been converted to their corresponding alcohols using the polymer supported Ru(III) catalyst. The effects of solvents, reaction time, catalyst amount for the azide–alkyne cycloaddition reaction and transfer-hydrogenation reaction were studied. This catalyst showed excellent catalytic activity and recyclability. The polymer supported Ru(III) catalyst could be easily recovered

  合成并表征了一种新的聚合物负载的Ru（III）配合物。该化合物的催化性能首次在水中进行了叠氮化物-炔烃环加成反应以及在露天中酮的转移加氢反应的测试。在上述催化剂的存在下，在水性介质中由叠氮化物和末端炔烃以优异的产率获得了1,4-二取代-1,2,3-三唑。使用聚合物负载的Ru（III）催化剂已将芳香族酮转化为其相应的醇。研究了溶剂，反应时间，叠氮化物-炔烃环加成反应和转移加氢反应的催化剂用量的影响。该催化剂显示出优异的催化活性和可回收性。聚合物负载的Ru（III）催化剂可通过过滤轻松回收，可重复使用五次以上，而不会明显损失其初始活性。没有观察到反应过程中从催化剂中浸出Ru的迹象，表明催化过程中存在真正的异质性。
• Solvent-free one-pot synthesis of 1,2,3-triazole derivatives by the ‘Click’ reaction of alkyl halides or aryl boronic acids, sodium azide and terminal alkynes over a Cu/Al₂O₃surface under ball-milling
  作者：Nirmalya Mukherjee、Sabir Ahammed、Sukalyan Bhadra、Brindaban C. Ranu

  DOI：10.1039/c2gc36521a

  日期：——

  followed by evaporation of the solvent. No chromatographic purification is required. The catalyst is recycled for subsequent reactions. The azides are produced in situ and thus this procedure avoids the handling of hazardous azides. This protocol offers broad scope for access to a variety of diversely substituted 1,2,3-triazoles. The use of no hazardous organic solvent, the use of ball-milling, and cost

  一锅法合成 1,2,3-三唑 通过三成分耦合的导数 烷基 （苄基） 卤化物 或芳基硼酸， 叠氮化钠 和终端 炔烃 超过 铜（II）硫酸盐 支持于 氧化铝（Cu / Al 2 O 3）在球下铣削 在没有任何 溶剂并且已经开发了添加剂。通过简单洗涤粗反应残余物以分离出产物。乙醇 其次是 蒸发 的 溶剂。无色谱纯化是必须的。这催化剂再循环用于后续反应。这叠氮化物是原位生产的，因此该程序避免了危险物品的处理叠氮化物。该协议为访问各种不同替代品提供了广阔的范围1,2,3-三唑。使用无有害有机物溶剂，使用滚珠铣削以及成本效益，可回收性 催化剂 多达八次运行而没有明显的活性损失和高产量的产品，使该过程更环保。
• 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.