5-(4-methylphenyl)-1-phenyl-1H-1,2,3-triazole | 68809-45-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-(4-methylphenyl)-1-phenyl-1H-1,2,3-triazole
• 英文别名: 5-(4-methylphenyl)-1-phenyl-1,2,3-triazole；1-phenyl-5-(4-tolyl)-1H-1,2,3-triazole；1-phenyl-5-(p-tolyl)-1H-1,2,3-triazole；1-phenyl-5-p-tolyl-1H-1,2,3-triazole；1-phenyl-5-p-tolyl-1H-[1,2,3]triazole；5-(4-Methylphenyl)-1-phenyltriazole
• CAS: 68809-45-0
• 化学式: C₁₅H₁₃N₃
• 分子量: 235.288
• InChiKey: IQJHCGGEEOTLKT-UHFFFAOYSA-N

物化性质

• 熔点：
  148-149 °C
• 沸点：
  421.5±43.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(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

• 作为产物：
  描述：

  2-(4-甲基苯基)乙醇 在 硫酰氟 、 potassium tert-butylate 、 potassium carbonate 作用下， 以 二甲基亚砜 为溶剂， 反应 14.0h， 生成 5-(4-methylphenyl)-1-phenyl-1H-1,2,3-triazole
  参考文献：
  名称：

  Transition-metal-free regioselective construction of 1,5-diaryl-1,2,3-triazoles through dehydrative cycloaddition of alcohols with aryl azides mediated by SO₂F₂

  摘要：

  开发了一种新颖、简单且实用的方法，用于高效、经济、具有区域选择性的合成高价值的1,5-二芳基-1,2,3-三唑。

  DOI：

  10.1039/c8cc09693g

文献信息

• Base-mediated reaction of vinyl bromides with aryl azides: one-pot synthesis of 1,5-disubstituted 1,2,3-triazoles
  作者：Luyong Wu、Yuxue Chen、Jianheng Luo、Qi Sun、Mingsheng Peng、Qiang Lin

  DOI：10.1016/j.tetlet.2014.03.029

  日期：2014.7

  been investigated in the process. A variety of 1,5-disubstituted triazoles were prepared in low to good yields. Further studies reveal that the corresponding alkynes were produced as intermediates via elimination reaction. Under the same reaction conditions, the reactions of alkyl alkynes with phenyl azide would give 1,5-disubstituted 1,2,3-triazoles.

  已经报道了叠氮化物与β-或α-乙烯基溴的一锅碱基介导的反应。在此过程中已研究了碱和溶剂的作用。各种1,5-二取代的三唑以低到好收率的方式制备。进一步的研究表明，相应的炔烃是通过消除反应生成的中间体。在相同的反应条件下，烷基炔烃与叠氮化苯的反应将生成1，5-二取代的1,2,3-三唑。
• A Metal-Free Multicomponent Cascade Reaction for the Regiospecific Synthesis of 1,5-Disubstituted 1,2,3-Triazoles
  作者：Guolin Cheng、Xiaobao Zeng、Jinhai Shen、Xuesong Wang、Xiuling Cui

  DOI：10.1002/anie.201307499

  日期：2013.12.9

  About specifics: A method for the regiospecific synthesis of the title compounds through an unprecedented Michael addition/deacylative diazo transfer/cyclization sequence has been established. The simple and practical method can be used for the modification of primary amines including chiral α‐amines. The process involves the formation three covalent bonds and the cleavage of two covalent bonds (see

  关于细节：已经建立了通过空前的迈克尔加成/去酰基重氮转移/环化序列进行区域特异性合成标题化合物的方法。简单实用的方法可用于伯胺（包括手性α-胺）的修饰。该过程涉及三个共价键的形成和两个共价键的裂解（参见方案，Ts = 4-甲苯磺酰基）。
• Palladium-Catalyzed Regioselective C-5 Arylation of 1,2,3-Triazoles with Diaryliodonium Salts
  作者：Zhengyin Du、Hua Feng、Fangli Gang、Yang Che、Ying Fu

  DOI：10.1055/s-0036-1588815

  日期：2017.8

  An effective method for C-5 arylation of 1,4-disubstituted 1,2,3-triazoles and C-5 regioselective arylation of 1-substituted 1,2,3-triazoles via sp2 C–H activation with palladium as a catalyst and diaryliodonium salts as arylating reagents is described. Various electron-rich and electron-deficient substituents attached to triazoles and diaryliodonium salts were tolerable to give the desired products

  1,4-二取代的1,2,3-三唑的C-5芳基化和1-取代的1,2,3-三唑的C-5区域选择性芳化的有效方法，通过sp2C-H活化，钯作为催化剂和描述了作为芳基化试剂的二芳基碘盐。连接到三唑和二芳基碘鎓盐的各种富电子和缺电子取代基在空气气氛下可耐受以在 24 小时内以良好的分离产率得到所需产物。
• Ln[N(SiMe3)2]3-catalyzed cycloaddition of terminal alkynes to azides leading to 1,5-disubstituted 1,2,3-triazoles: new mechanistic features
  作者：Longcheng Hong、Weijia Lin、Fangjun Zhang、Ruiting Liu、Xigeng Zhou

  DOI：10.1039/c3cc42534g

  日期：——

  The first example of rare earth metal-catalyzed cycloaddition of terminal alkynes to azides resulting in the formation of 1,5-disubstituted 1,2,3-triazoles is described. Preliminary studies revealed that the present cycloaddition shows unprecedented mechanistic features involving a tandem anionic cascade cyclization and anti-addition across the CC triple bond.

  首例稀土金属催化的末端炔烃与叠氮化合物的环加成反应，生成1,5-二取代的1,2,3-三唑，已被报道。初步研究表明，这一环加成反应展现出前所未有的机理特征，涉及串联的阴离子级联环化和反式加成穿过碳碳三键。
• Potassium tert-Butoxide Promoted Cycloaddition Reaction for the Synthesis of 1,5-Disubstituted 1,2,3-Triazoles from Aromatic Azides and Trimethylsilyl-Protected Alkynes
  作者：Luyong Wu、Yuxue Chen、Mi Tang、Xinming Song、Guangying Chen、Xiaoping Song、Qiang Lin

  DOI：10.1055/s-0031-1291042

  日期：2012.6

  cycloaddition reaction of aromatic azides and trimethylsilyl alkynes upon treatment with desilylating reagents was investigated. In the process, the use of t-BuOK in wet DMF generated 1,5-disubstituted 1,2,3-triazoles regioselectively in moderate to good yields at ambient temperature.

  研究了芳族叠氮化物和三甲基甲硅烷基炔烃在用脱甲硅烷基化试剂处理后的环加成反应。在该过程中，在湿 DMF 中使用 t-BuOK 在环境温度下以中等至良好的产率区域选择性地生成 1,5-二取代的 1,2,3-三唑。