4-phenyl-1-(m-tolyl)-1H-1,2,3-triazole | 1222130-97-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-phenyl-1-(m-tolyl)-1H-1,2,3-triazole
• 英文别名: 1-(3-tolyl)-4-phenyl-1H-1,2,3-triazole；1-(3-Methylphenyl)-4-phenyl-1H-1,2,3-triazole；1-(3-methylphenyl)-4-phenyltriazole
• CAS: 1222130-97-3
• 化学式: C₁₅H₁₃N₃
• 分子量: 235.288
• InChiKey: SSCQVPPLJQVTQL-UHFFFAOYSA-N

物化性质

• 沸点：
  432.6±48.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  30.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  甲醇 、 4-phenyl-1-(m-tolyl)-1H-1,2,3-triazole 在 dipotassium peroxodisulfate 、 palladium diacetate 作用下， 反应 12.0h， 以81%的产率得到4-(2,6-dimethoxyphenyl)-1-(m-tolyl)-1H-1,2,3-triazole
  参考文献：
  名称：

  Palladium-catalyzed selective ortho C–H alkoxylation at 4-aryl of 1, 4-disubstituted 1, 2, 3-triazoles

  摘要：

  The ortho- C H bonds at C(4)-aryl of 1, 4-disubstituted 1, 2, 3-triazoles were regioselectively alkoxylated in good to excellent yields with under the directing of the triazole ring. Some products were found to exhibit strong antifungal capacity to fight against root-rot disease of Panax notoginseng by testing the minimum inhibitory concentration (MIC). (C) 2020 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2020.130985
• 作为产物：
  描述：

  苯乙酮 在 copper diacetate 、 三甲基乙酸 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 13.0h， 生成 4-phenyl-1-(m-tolyl)-1H-1,2,3-triazole
  参考文献：
  名称：

  铜介导的N-甲苯磺酰hydr和苯胺合成1,2,3-三唑

  摘要：

  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。

  DOI：

  10.1002/anie.201306416

文献信息

• One-pot synthesis of 1,4-disubstituted 1,2,3-triazoles from nitrobenzenes
  作者：Fen Zhao、Zhen Chen、Kai Xie、Rui Yang、Yu-Bo Jiang

  DOI：10.1016/j.cclet.2015.09.021

  日期：2016.1

  Abstract A facile synthesis of 1,4-disubstituted 1,2,3-triazoles was achieved from nitrobenzenes and terminal alkynes under mild conditions. The reactions were successful for nitrobenzenes and terminal alkynes bearing various functionalities, from which the 1,2,3-triazole derivatives were smoothly synthesized through a four-step one-pot sequence.

  摘要在温和的条件下，由硝基苯和末端炔烃轻松合成了1,4-二取代的1,2,3-三唑。对于具有各种功能的硝基苯和末端炔烃，反应是成功的，通过四步一锅法平稳地合成了1,2,3-三唑衍生物。
• An Efficient Copper-Catalyzed One-Pot Synthesis of 1-Aryl-1,2,3-triazoles from Arylboronic Acids in Water under Mild Conditions
  作者：Changbo Hao、Changjian Zhou、Jianwei Xie、Jie Zhang、Ping Liu、Bin Dai

  DOI：10.1002/cjoc.201500643

  日期：2015.11

  A convenient method for one‐pot two‐step 1,3‐dipolar cycloadditon reaction of arylboronic acid, sodium azide followed with terminal alkynes in the presence of 2‐pyrrolecarbaldiminato‐Cu(II) complexes catalyst is reported. Various 1‐aryl‐1,2,3‐triazoles were prepared in 63%–97% yields in water at 30°C without any additives and avoiding the isolation of unstable aryl azides.

  报道了一种在2-吡咯碳烷基二氨基-Cu（II）络合物催化剂存在下，芳基硼酸，叠氮化钠与末端炔烃进行单锅两步1,3-偶极环己二酮反应的简便方法。在30°C的水中制备各种1-芳基1,2,3-三唑的产率为63％–97％，没有任何添加剂，并且避免了不稳定的芳基叠氮化物的分离。
• Copper-γ-cyclodextrin complexes immobilized on hexagonal boron nitride as an efficient catalyst in the multicomponent synthesis of 1,2,3-triazoles
  作者：Ruifang Nie、Rui Sang、Xiaojun Ma、Yang Zheng、Xu Cheng、Weijian Li、Li Guo、Hui Jin、Yong Wu

  DOI：10.1016/j.jcat.2016.09.022

  日期：2016.12

  recoverable and reusable heterogeneous catalyst can be used in the click synthesis of 1,2,3-triazoles via a one-pot three-component reaction of boracic acid, terminal alkynes, and sodium azide at room temperature in water. FT-IR, XRD, SEM, XPS, TG, and ICP-AES techniques were used to characterize the catalyst. In general, this reaction, with the aid of this new catalyst, afforded the corresponding products

  首次制备了固定在六方氮化硼上的铜-γ-环糊精配合物（h [受电子邮件保护]γ[受电子邮件保护]（OAc）2）。这种可回收和可重复使用的非均相催化剂可在室温下于水中通过硼酸，末端炔烃和叠氮化钠的一锅式三组分反应用于1,2,3-三唑的点击合成。FT-IR，XRD，SEM，XPS，TG和ICP-AES技术用于表征催化剂。通常，在这种新型催化剂的帮助下，该反应得到具有良好产率和对官能团的优异耐受性的相应产物。
• Aqueous bile salt accelerated cascade synthesis of 1,2,3-triazoles from arylboronic acids
  作者：Anirban Garg、Abdul Aziz Ali、Krishnaiah Damarla、Arvind Kumar、Diganta Sarma

  DOI：10.1016/j.tetlet.2018.09.064

  日期：2018.11

  A facile, efficient and mild copper catalyzed strategy for cascade synthesis of various 1,4-disubstituted 1,2,3-triazoles from arylboronic acids, sodium azide and alkynes was developed by using aqueous bile salt NaDC solution as an accelerating medium. Low catalyst loading (only 1 mol% Cu source was sufficient for in situ generation of azide followed by azide–alkyne coupling), green solvent, use of

  通过使用胆汁盐NaDC水溶液作为促进介质，开发了一种简便，高效，温和的铜催化策略，用于从芳基硼酸，叠氮化钠和炔烃级联合成各种1,4-二取代的1,2,3-三唑。低催化剂负载量（仅1 mol％的铜源足以就地生成叠氮化物，然后进行叠氮化物-炔烃偶联反应），绿色溶剂，使用生物表面活性剂作为添加剂以及较短的反应时间使该方案高度可访问且对环境友好。
• 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。