1H-1,2,3-三唑,4-(4-溴苯基)-1-苯基- | 13178-00-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 1H-1,2,3-三唑,4-(4-溴苯基)-1-苯基-
• 英文名称: 4-(4-bromophenyl)-1-phenyl-1H-1,2,3-triazole
• 英文别名: 4-(4-bromophenyl)-1-phenyltriazole
• CAS: 13178-00-2
• 化学式: C₁₄H₁₀BrN₃
• 分子量: 300.157
• InChiKey: DPCGHVRNHBDTBO-UHFFFAOYSA-N

物化性质

• 熔点：
  224 °C
• 沸点：
  456.8±37.0 °C(Predicted)
• 密度：
  1.46±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  18
• 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：
  30.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2'-氯-4-溴苯乙酮 在 oxygen 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 生成 1H-1,2,3-三唑,4-(4-溴苯基)-1-苯基-
  参考文献：
  名称：

  Aerobic Oxidative Cycloaddition of α-Chlorotosylhydrazones with Arylamines: General Chemoselective Construction of 1,4-Disubstituted and 1,5-Disubstituted 1,2,3-Triazoles under Metal-Free and Azide-Free Conditions

  摘要：

  A novel synthetic approach toward 1,4-disubstituted 1,2,3-triazoles and 1,5-disubstituted 1,2,3-triazoles by aerobic oxidative cycloaddition of alpha-chlorotosylhydrazone with primary aryl amine has been developed. Significantly, the reaction proceeds smoothly to afford 1,4-disubstituted 1,2,3-triazoles and 1,5-disubstituted 1,2,3-triazoles under catalyst-free, metal-free, azide-free, and peroxide-free conditions.

  DOI：

  10.1021/acs.orglett.5b01000

文献信息

• An Organocatalytic Azide-Aldehyde [3+2] Cycloaddition: High-Yielding Regioselective Synthesis of 1,4-Disubstituted 1,2,3-Triazoles
  作者：Dhevalapally B. Ramachary、Adluri B. Shashank、S. Karthik

  DOI：10.1002/anie.201406721

  日期：2014.9.22

  An organocatalytic azide–aldehyde [3+2] cycloaddition (organo‐click) reaction of a variety of enolizable aldehydes is reported. The organo‐click reaction is characterized by a high rate and regioselectivity, mild reaction conditions, easily available substrates with simple operation, and excellent yields with a broad spectrum of substrates. It constitutes an alternative to the previously known CuAAC

  报道了多种可烯化醛的有机催化叠氮化物-醛[3 + 2]环加成（有机点击）反应。有机点击反应的特点是高速率和区域选择性，温和的反应条件，易于获得的底物和简单的操作，以及具有广泛底物范围的优异收率。它构成了以前已知的CuAAC，RuAAC和IrAAC点击反应的替代方法。
• Copper-Mediated Synthesis of 1,2,3-Triazoles from<i>N</i>-Tosylhydrazones and Anilines
  作者：Zhengkai Chen、Qiangqiang Yan、Zhanxiang Liu、Yiming Xu、Yuhong Zhang

  DOI：10.1002/anie.201306416

  日期：2013.12.9

  NNNifty targets: In a straightforward copper‐mediated synthesis of 1,4‐disubstituted and 1,4,5‐trisubstituted 1,2,3‐triazoles, readily available aniline and N‐tosylhydrazone substrates underwent cyclization through CN and NN bond formation (see scheme; Piv=pivaloyl, Ts=p‐toluenesulfonyl). This method enables the preparation of 1,2,3‐triazoles with high efficiency under mild conditions without the

  NNNifty目标：在1,4-二取代和1,4,5-三取代的1,2,3-三唑，容易获得的苯胺和一个简单的铜介导的合成Ñ -tosylhydrazone基板至C后行环化 N和N  Ñ键的形成（参见方案； Piv =新戊酰基，Ts =对甲苯磺酰基）。该方法可以在温和条件下高效地制备1,2,3-三唑，而无需使用叠氮化物。
• Metal-Free CN- and NN-Bond Formation: Synthesis of 1,2,3-Triazoles from Ketones,<i>N</i>-Tosylhydrazines, and Amines in One Pot
  作者：Zhengkai Chen、Qiangqiang Yan、Zhanxiang Liu、Yuhong Zhang

  DOI：10.1002/chem.201405057

  日期：2014.12.22

  A novel synthetic approach toward 1,4‐disubstituted 1,2,3‐triazoles by CN‐ and NN‐bond formation has been established under transition‐metal‐free conditions. Complete control of the regioselectivity was successfully achieved. Commercially available anilines, ketones, and N‐tosylhydrazine were treated with molecular iodine in one pot to allow the regioselective generation of 1,4‐disubstituted 1,2

  在无过渡金属的条件下，已经建立了一种通过CN和NN键形成1,4-二取代的1,2,3-三唑的新颖合成方法。成功实现了对区域选择性的完全控制。在一个锅中用分子碘处理市售的苯胺，酮和N-甲苯磺酰肼，从而可以在不使用叠氮化物的情况下高选择性地生成1,4-二取代的1,2,3-三唑。
• Novel Cu(0)–Fe3O4@SiO2/NH2cel as an Efficient and Sustainable Magnetic Catalyst for the Synthesis of 1,4-Disubstituted-1,2,3-triazoles and 2-Substituted-Benzothiazoles via One-Pot Strategy in Aqueous Media
  作者：Madhvi Bhardwaj、Babita Jamwal、Satya Paul

  DOI：10.1007/s10562-015-1672-7

  日期：2016.3

  A novel, air stable, water dispersible and efficient magnetic catalyst based on copper nanoparticles onto ethylene diamine functionalized inorganic/organic composite [Cu(0)–Fe3O4@SiO2/NH2cel] has been prepared. Functionalization of inorganic/organic composite by ethylene diamine imparts desirable chemical functionality and enables the generation of active sites for the immobilization of Cu(0) nanoparticles

  已经制备了一种基于铜纳米粒子在乙二胺官能化无机/有机复合材料 [Cu(0)–Fe3O4@SiO2/NH2cel] 上的新型、空气稳定、水分散性和高效的磁性催化剂。乙二胺对无机/有机复合材料的官能化赋予了理想的化学功能，并能够产生用于固定 Cu(0) 纳米颗粒的活性位点。新型催化剂体系已通过各种技术得到很好的表征，如 FTIR、TGA、XRD、SEM、HRTEM、EDX、ICP-AES、UV-Vis 和 VSM。此外，Cu(0)– @SiO2/NH2cel 开辟了一条新途径，引入了一种非常有用且高效的催化系统，用于通过 1,3 -末端乙炔偶极环加成到叠氮化物，在室温下由苯胺在水中原位生成，以2-碘苯胺、醛、硫脲为硫源的一锅三组分反应在水中合成2-取代苯并噻唑衍生物。新型多相磁性催化剂具有可回收性，催化活性不会显着降低，并且可以使用外部磁铁轻松回收，从而使其环保且经济地进行所需的转化。图形摘要
• Iodine-mediated C–N and N–N bond formation: a facile one-pot synthetic approach to 1,2,3-triazoles under metal-free and azide-free conditions
  作者：Geeta Sai Mani、Kavitha Donthiboina、Siddiq Pasha Shaik、Nagula Shankaraiah、Ahmed Kamal

  DOI：10.1039/c9ra06005g

  日期：——

  A novel strategy towards the synthesis of 1,4-disubstituted 1,2,3-triazoles via C–N and N–N bond formation has been demonstrated under transition metal-free and azide-free conditions. These 1,2,3-triazoles were obtained in a regioselective manner from commercially available anilines, aryl alkenes/aryl alkynes and N-tosylhydrazines using I2 under O2 atmosphere. Broad substrate scope, milder reaction

  在无过渡金属和无叠氮化物的条件下，已经证明了一种通过C-N 和 N-N 键形成合成 1,4-二取代 1,2,3-三唑的新策略。这些1,2,3-三唑是在O 2气氛下使用I 2从市售苯胺、芳基烯烃/芳基炔烃和N-甲苯磺酰肼以区域选择性方式获得的。广泛的底物范围、较温和的反应条件、良好至中等的产率和清洁方案是该方法的显着特点。此外，该协议适用于生成医学上重要的关键构建块库。