4-phenyl-2-tosyl-2H-1,2,3-triazole | 1209494-83-6

• 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-2-tosyl-2H-1,2,3-triazole
• 英文别名: 2-tosyl-4-phenyl-1,2,3-triazole；4-phenyl-2-p-tosyl-2H-1,2,3-triazole；4-phenyl-2-tosyl-1,2,3-triazole；2-(4-Methylphenyl)sulfonyl-4-phenyltriazole；2-(4-methylphenyl)sulfonyl-4-phenyltriazole
• CAS: 1209494-83-6
• 化学式: C₁₅H₁₃N₃O₂S
• 分子量: 299.353
• InChiKey: ISEJGTJVSREUIH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 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：
  73.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-phenyl-2-tosyl-2H-1,2,3-triazole 在 4-二甲氨基吡啶 作用下， 以 乙腈 为溶剂， 反应 12.0h， 以10%的产率得到1-(4-methylbenzensulfonyl)-4-phenyl-1H-1,2,3-triazole
  参考文献：
  名称：

  Preparation of 2-Sulfonyl-1,2,3-triazoles by Base-Promoted 1,2-Rearrangement of a Sulfonyl Group

  摘要：

  1,2-Rearrangement of a sulfonyl group occurs on treatment of 1-sulfony1-1,2,3-triazoles with a catalytic amount of 4-dimethylaminopyridine (DMAP) in acetonitrile to give an equilibrium mixture of 1-sulfonyl- and 2-sulfonyl derivatives, with considerable predominance of the latter. Subsequent acidic treatment of the mixture caused selective hydrolysis of the 1-sulfonyl derivative, which led to the isolation of the 2-sulfony1-1,2,3-triazole in good total yield in a pure form.

  DOI：

  10.3987/com-09-s(s)44
• 作为产物：
  描述：

  1-(4-methylbenzensulfonyl)-4-phenyl-1H-1,2,3-triazole 在 4-二甲氨基吡啶 、 溶剂黄146 作用下， 以 乙腈 、 水 为溶剂， 反应 15.0h， 以82%的产率得到4-phenyl-2-tosyl-2H-1,2,3-triazole
  参考文献：
  名称：

  Preparation of 2-Sulfonyl-1,2,3-triazoles by Base-Promoted 1,2-Rearrangement of a Sulfonyl Group

  摘要：

  1,2-Rearrangement of a sulfonyl group occurs on treatment of 1-sulfony1-1,2,3-triazoles with a catalytic amount of 4-dimethylaminopyridine (DMAP) in acetonitrile to give an equilibrium mixture of 1-sulfonyl- and 2-sulfonyl derivatives, with considerable predominance of the latter. Subsequent acidic treatment of the mixture caused selective hydrolysis of the 1-sulfonyl derivative, which led to the isolation of the 2-sulfony1-1,2,3-triazole in good total yield in a pure form.

  DOI：

  10.3987/com-09-s(s)44

文献信息

• Base free regioselective synthesis of α-triazolylazine derivatives
  作者：Mysore Bhyrappa Harisha、Muthupandi Nagaraj、Shanmugam Muthusubramanian、Nattamai Bhuvanesh

  DOI：10.1039/c6ra10452e

  日期：——

  A regioselective α-heteroarylation followed by deoxygenation towards the synthesis of variety of azine triazole from simple azine N-oxides derivatives and N-tosyl-1,2,3-triazoles has been described. The reaction is metal free and base free with shorter reaction time, high yields and a broad substrate scope.

  已经描述了区域选择性α-杂芳基化，然后脱氧以从简单的嗪N-氧化物衍生物和N-甲苯磺酰基-1,2,3-三唑合成各种嗪三唑。该反应是无金属和无碱的，反应时间更短，产率高且底物范围广。
• Reactivity of 1,2,3-triazoles towards sulfonyl chlorides. A novel approach to 1- and 2-sulfonyl-4-azolyl-1,2,3-triazoles
  作者：Tetyana V. Beryozkina、Ilya V. Efimov、Walter M.F. Fabian、Nikolai A. Beliaev、Pavel A. Slepukhin、Maxim L. Isenov、Wim Dehaen、Gert Lubec、Oleg S. Eltsov、Zhijin Fan、Joice Thomas、Vasiliy A. Bakulev

  DOI：10.1016/j.tet.2015.06.088

  日期：2015.9

  The reactions of N-unsubstituted triazoles with sulfonyl chlorides afforded mixtures of regioisomeric 1- and 2-sulfonyl-1,2,3-triazoles. In some cases, pure regioisomers were obtained by crystallization of mixtures of isomers. 1,2,3-Triazoles bearing thiadiazole, isoxazole and benzene rings react with mesyl chloride and tosyl chloride to form mainly 1-substituted 1,2,3-triazoles. Conversely, reactions

  的反应ñ -未被取代的具有得到区域异构1-和2-磺酰基-1,2,3-三唑的混合物磺酰氯三唑。在某些情况下，纯的区域异构体是通过异构体混合物的结晶获得的。带有噻二唑，异恶唑和苯环的1,2,3-三唑与甲磺酰氯和甲苯磺酰氯反应，主要形成1-取代的1,2,3-三唑。相反，三唑1a，b和恶二唑基三唑1h与更庞大的1-（2,4-二甲基苯基）磺酰氯的反应主要得到2-取代的产物。恶二唑1b提供了区域异构产物3和4的均等混合物与甲磺酰和甲苯磺酰氯反应的结果。较高的温度增加了异构体的比例，有利于2-取代的三唑。异构体的比例取决于偶氮基环的性质和磺酰氯中取代基的大小。根据实验和理论数据的结果，可以将1-取代和2-取代的1,2,3-三唑视为动力学和热力学产物。
• <i>p</i>-Toluenesulfonic acid-promoted autocatalytic hydrolyzation of 1-tosyl-1,2,3-triazoles
  作者：Haohao Dong、Dongdong Zhang、Renjie Fang、Qingyang Du、Zhuoya Dong、Hao Wei、Min Shi、Feijun Wang

  DOI：10.1080/00397911.2018.1440316

  日期：2018.5.19

  ABSTRACT The first example of autocatalytic hydrolyzation of 4-aryl-1-tosyl-1,2,3-triazoles induced by p-toluenesulfonic acid was reported, providing an effective and metal-free synthetic approach to deliver a broad range of new 4-aryl-2H-1,2,3-triazoles in good yields. The kinetic profile of this hydrolyzation suggested that this reaction has exponential autocatalytic behavior. GRAPHICAL ABSTRACT

  摘要报道了对甲苯磺酸诱导 4-芳基-1-甲苯磺酰基-1,2,3-三唑自催化水解的第一个例子，提供了一种有效且无金属的合成方法，以提供广泛的新型 4-芳基-2H-1,2,3-三唑，收率良好。该水解的动力学曲线表明该反应具有指数自催化行为。图形概要
• Metal-free, highly regioselective sulfonylation of NH-1,2,3-triazoles with sodium sulfinates and thiosulfonates
  作者：Raju Jannapu Reddy、Angothu Shankar、Md. Waheed、Jagadeesh Babu Nanubolu

  DOI：10.1016/j.tetlet.2018.04.023

  日期：2018.5

  A convenient and metal-free protocol for the highly regioselective sulfonylation of NH-1,2,3-triazoles is described. A range of readily accessible NH-1,2,3-triazoles were sulfonylated with various aryl sulfinates in the presence of molecular iodine. The scope was extended to thiosulfonates as an efficient sulfonylating agent and nitrochromene derived triazoles were also explored for selective N-sulfonylation. A variety of synthetically viable N-2-sulfonyl triazoles were obtained in moderate to high yields with excellent regioselectivities via N-S bond construction under mild reaction conditions. (C) 2018 Elsevier Ltd. All rights reserved.
• Visible-Light-Promoted α-C(sp³)–H Amination of Ethers with Azoles and Amides
  作者：Yaqi Deng、Zongjing Hu、Jian Xue、Jiabin Yin、Tong Zhu、Shunying Liu

  DOI：10.1021/acs.orglett.3c04291

  日期：2024.2.2