4-(4-methoxyphenyl)-1-phenyl-1H-1,2,3-triazole | 68809-41-6

• 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-(4-methoxyphenyl)-1-phenyl-1H-1,2,3-triazole
• 英文别名: 4-(4-methoxyphenyl)-1-phenyl-1,2,3-triazole；4-(4-methoxyphenyl)-1-phenyltriazole
• CAS: 68809-41-6
• 化学式: C₁₅H₁₃N₃O
• 分子量: 251.288
• InChiKey: ITOAUBAZZJQQEG-UHFFFAOYSA-N

物化性质

• 熔点：
  152.5-154.5 °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

• 作为反应物：
  描述：

  4-(4-methoxyphenyl)-1-phenyl-1H-1,2,3-triazole 在 氢溴酸 作用下， 以46 %的产率得到4-(1-phenyl-1H-1,2,3-triazol-4-yl)phenol
  参考文献：
  名称：

  CN116589418

  摘要：

  公开号：
• 作为产物：
  描述：

  2-氯-4-甲氧基苯乙酮 在 氧气 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 生成 4-(4-methoxyphenyl)-1-phenyl-1H-1,2,3-triazole
  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 efficient CuI/DBU-catalyzed one-pot protocol for synthesis of 1,4-disubstituted 1,2,3-triazoles
  作者：Yuqin Jiang、Xingfeng Li、Yaru Zhao、Shuhong Jia、Mingrui Li、Zhiqi Zhao、Ruili Zhang、Wei Li、Weiwei Zhang

  DOI：10.1039/c6ra23789d

  日期：——

  A convenient CuI/DBU catalyzed one-pot method has been developed for the synthesis of 1,4-disubstituted 1,2,3-triazoles through the coupling of aryl iodides with sodium azide, followed by the intermolecular cyclization between the generated aryl azides and phenylacetaldehyde derivatives or alkynes in DMSO. The established protocol was compatible with a wide scope of substrates in good to excellent

  通过芳基碘化物与叠氮化钠的偶合反应，然后在生成的芳基叠氮化物和芳烃之间进行分子间环化反应，已经开发了一种方便的CuI / DBU催化一锅法，用于合成1,4-二取代的1,2,3-三唑。 DMSO中的苯乙醛衍生物或炔烃。既定的方案以良好至优异的产率与广泛范围的底物相容。
• Click chemistry from organic halides, diazonium salts and anilines in water catalysed by copper nanoparticles on activated carbon
  作者：Francisco Alonso、Yanina Moglie、Gabriel Radivoy、Miguel Yus

  DOI：10.1039/c1ob05735a

  日期：——

  An easy-to-prepare, reusable and versatile catalyst consisting of oxidised copper nanoparticles on activated carbon has been fully characterised and found to effectively promote the multicomponent synthesis of 1,2,3-triazoles from organic halides, diazonium salts, and aromatic amines in water at a low copper loading.

  一种易于制备、可重复使用且具有多功能性的催化剂，由氧化铜纳米颗粒负载于活性炭上构成，经过充分表征并发现其能有效促进1,2,3-三唑的多组分合成。该合成过程以有机卤化物、重氮盐和芳香胺为原料，在水相中进行，且铜的用量较低。
• 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。
• Application of two magnetic nanoparticle-supported copper(I) catalysts for the synthesis of triazole derivatives
  作者：Leila Mohammadi、Mohammad Ali Zolifgol、Meysam Yarie、Mahsa Ebrahiminia、Kenneth P. Roberts、Syed R. Hussaini

  DOI：10.1007/s11164-019-03864-7

  日期：2019.10

  Catalytic performance of two magnetically recoverable copper(I) complexes is reported for the synthesis of 1,2,3-triazole derivatives. Boronic acids and alkyl halides, in the presence of either catalyst, react with terminal alkynes and NaN3, forming 1,2,3-triazole derivatives in good yields. Both catalysts are easily recoverable and show a high potential of reusability.

  据报道，两种磁性可回收的铜（I）配合物的催化性能可用于合成1,2,3-三唑衍生物。在任何一种催化剂的存在下，硼酸和卤代烷与末端炔烃和NaN 3反应，以高收率形成1,2,3-三唑衍生物。两种催化剂都易于回收，并且显示出很高的可重复使用性。