1-(4-methoxyphenyl)-5-phenyl-1H-1,2,3-triazole | 2034-28-8

• 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-(4-methoxyphenyl)-5-phenyl-1H-1,2,3-triazole
• 英文别名: 1-(4-Methoxyphenyl)-5-phenyltriazole
• CAS: 2034-28-8
• 化学式: C₁₅H₁₃N₃O
• 分子量: 251.288
• InChiKey: HVNRGJHOHLHHPT-UHFFFAOYSA-N

物化性质

• 熔点：
  85 °C
• 沸点：
  445.4±47.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 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：
  39.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-(4-methoxyphenyl)-5-phenyl-Δ²-1,2,3-triazoline 在 potassium permanganate 、 四丁基氯化铵 作用下， 以 水 、 苯 为溶剂， 反应 4.0h， 以61%的产率得到1-(4-methoxyphenyl)-5-phenyl-1H-1,2,3-triazole
  参考文献：
  名称：

  Kadaba, Pankaja K., Journal fur praktische Chemie (Leipzig 1954), 1982, vol. 324, # 5, p. 857 - 864

  摘要：

  DOI：

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 general metal-free route towards the synthesis of 1,2,3-triazoles from readily available primary amines and ketones
  作者：Joice Thomas、Sampad Jana、Jubi John、Sandra Liekens、Wim Dehaen

  DOI：10.1039/c5cc08347h

  日期：——

  An unprecedented approach that enables the direct and selective preparation of 1,5-disubstituted 1,2,3-triazoles from abundantly available building blocks such as primary amines, enolizable ketones and 4-nitrophenyl azide as a renewable...

  一种前所未有的方法，可以从伯胺，可烯醇化的酮和4-硝基苯叠氮化物等可再生原料中大量获得，直接和选择性地制备1,5-二取代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）。
• Discovery of a Robust and Efficient Homogeneous Silver(I) Catalyst for the Cycloaddition of Azides onto Terminal Alkynes
  作者：James McNulty、Kunal Keskar

  DOI：10.1002/ejoc.201200930

  日期：2012.10

  A highly efficient, chemically stable, and well-defined homogeneous silver(I) catalyst is reported for the cycloaddition of azides onto terminal alkynes (Ag-AAC reaction). The Ag-AAC reaction occurs at room temperature or with heating to deliver exclusively the corresponding 1,4-triazole. A pronounced ligand effect was discovered through systematic modification to the ligand structure resulting in

  据报道，一种高效、化学稳定且定义明确的均相银 (I) 催化剂用于叠氮化物在末端炔烃上的环加成反应（Ag-AAC 反应）。Ag-AAC 反应发生在室温下或加热以专门提供相应的 1,4-三唑。通过对配体结构进行系统修饰，发现了显着的配体效应，从而发现了用于该反应的化学稳定的活性催化剂。
• 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。