4-(1-(4-methoxyphenyl)-1H-1,2,3-triazol-4-yl)benzonitrile | 1274355-63-3

• 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-(1-(4-methoxyphenyl)-1H-1,2,3-triazol-4-yl)benzonitrile
• 英文别名: 4-[1-(4-Methoxyphenyl)triazol-4-yl]benzonitrile
• CAS: 1274355-63-3
• 化学式: C₁₆H₁₂N₄O
• 分子量: 276.297
• InChiKey: IMPPOOAZVSYZMP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  63.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  甲氧苯胺 在 盐酸 、 sodium nitrite 作用下， 以 水 为溶剂， 反应 8.13h， 生成 4-(1-(4-methoxyphenyl)-1H-1,2,3-triazol-4-yl)benzonitrile
  参考文献：
  名称：

  银-石墨烯纳米复合材料的合成及其在水中一锅三组分偶联反应和一锅合成1,4-二取代1,2,3-三唑的催化应用†

  摘要：

  已经通过简单的化学路线合成了具有银纳米颗粒的石墨烯基复合材料，并且已经通过一锅法测试了其催化活性用于多组分反应和点击反应。这种银-石墨烯纳米复合材料在室温下对醛，炔烃和胺之间的三组分偶联（A 3偶联）和通过点击反应一锅法合成1,4-二取代的1,2,3-三唑显示出出色的催化活性。原位之间生成的叠氮化物（衍生自苯胺或胺）和末端乙炔。该固体银-石墨烯催化剂已通过TEM，拉曼光谱，XRD和UV-可见吸收光谱进行了表征。所开发的催化剂是空气稳定的，便宜的，易于制备的，并且可以容易地回收和重复使用五次而不会显着降低活性和选择性。

  DOI：

  10.1039/c3ra47466f

文献信息

• Combinatorial synthesis of new fluorescent scaffolds using click chemistry
  作者：Felix Cleemann、Wendy Loa Kum-Cheung、Peter Karuso

  DOI：10.1016/j.tetlet.2021.153520

  日期：2022.1

  bio-orthogonal functional groups that can be readily coupled using copper(I)- or ruthenium(II)- catalyzed 1,3-dipolar cycloaddition reactions. Using non-fluorescent aromatic azides and aromatic acetylenes, covering a range of electron rich and poor building blocks, the Huisgen cycloaddition afford 1,4-disubstituted or 1,5-disubstituted 1,2,3-triazoles. Using a combinatorial approach by running reaction in parallel

  叠氮化物和乙炔是生物正交官能团，可以使用铜 (I) 或钌 (II) 催化的 1,3-偶极环加成反应轻松偶联。使用非荧光芳香叠氮化物和芳香乙炔，覆盖了一系列富电子和贫电子结构单元，Huisgen 环加成得到 1,4-二取代或 1,5-二取代的 1,2,3-三唑。使用通过在聚丙烯 96 孔板中并行运行反应的组合方法，我们发现了几种新的荧光 1,2,3-三唑支架。这些化合物显示出与生物分子的多种相互作用，可以在生物学中找到应用，例如荧光显微镜或生物分子量化。
• Polymer anchored Cu(ii) complex: an efficient and recyclable catalytic system for the one-pot synthesis of 1,4-disubstituted 1,2,3-triazoles starting from anilines in water
  作者：Susmita Roy、Tanmay Chatterjee、Sk. Manirul Islam

  DOI：10.1039/c3gc41114a

  日期：——

  An efficient procedure for the one-pot synthesis of 1,4-disubstituted 1,2,3-triazole derivatives has been developed by the ‘click’ reaction of azides generated in situ from anilines or amines and terminal acetylenes catalyzed by the polymer anchored Cu(II) catalyst in water without using any additives. The polymer anchored Cu(II) catalyst was synthesized and its catalytic activity was evaluated in

  一锅合成1,4-二取代的有效方法 1,2,3-三唑 衍生产品是通过以下方式的“点击”反应开发的： 叠氮化物从原位产生苯胺 或者 胺类 和终端 乙炔 由...催化 聚合物锚固的铜（II）催化剂 在 水不使用任何添加剂。这聚合物锚固的铜（II）催化剂合成并首次在Huisgen [3 + 2]环加成反应中评估其催化活性。该协议具有以下优点：催化剂 装载，高收率，清洁反应，可回收利用 催化剂，在 水，不使用有害有机物 溶剂 用于产品纯化和一锅合成 三唑 从 苯胺 或者 胺类。
• Synthesis of silver–graphene nanocomposite and its catalytic application for the one-pot three-component coupling reaction and one-pot synthesis of 1,4-disubstituted 1,2,3-triazoles in water
  作者：Noor Salam、Arjyabaran Sinha、Anupam Singha Roy、Paramita Mondal、Nikhil R. Jana、Sk Manirul Islam

  DOI：10.1039/c3ra47466f

  日期：——

  reaction between in situ generated azides (derived from anilines or amines) and terminal acetylenes. This solid silver–graphene catalyst has been characterized by TEM, Raman, XRD and UV-Visible absorption spectra. The developed catalyst is air-stable, inexpensive, easy to prepare and can be facilely recovered and reused five times without significant decrease in activity and selectivity.

  已经通过简单的化学路线合成了具有银纳米颗粒的石墨烯基复合材料，并且已经通过一锅法测试了其催化活性用于多组分反应和点击反应。这种银-石墨烯纳米复合材料在室温下对醛，炔烃和胺之间的三组分偶联（A 3偶联）和通过点击反应一锅法合成1,4-二取代的1,2,3-三唑显示出出色的催化活性。原位之间生成的叠氮化物（衍生自苯胺或胺）和末端乙炔。该固体银-石墨烯催化剂已通过TEM，拉曼光谱，XRD和UV-可见吸收光谱进行了表征。所开发的催化剂是空气稳定的，便宜的，易于制备的，并且可以容易地回收和重复使用五次而不会显着降低活性和选择性。
• Installation/Modulation of the Emission Response via Click Reaction
  作者：Subhendu Sekhar Bag、Rajen Kundu

  DOI：10.1021/jo200231k

  日期：2011.5.6

  We have demonstrated the installation of a fluorescence property into a nonfluorescent precursor and modulation of an emission response of a pyrene fluorophore via click reaction. The synthesized fluorophores show different solvatochromicity and/or intramolecular charge transfer (ICT) feature as is revealed from the UV-visible, fluorescence photophysical properties of these fluorophores, and DFT/TDDFT calculation. We observed that some of the synthesized fluorophores showed purely ICT character while emission from some of them arose from the LE state. A structureless and solvent polarity-sensitive dual emission behavior was observed for one of the triazolylpyrene fluorophores that contains an electron-donating -NMe(2) substituent (fluorophore, 7a). Conversely, triazolylpyrene with an electron-withdrawing -CN group (fluorophore, 7b) showed a solvent polarity-independent vibronic emission. The effect of ICT on the photophysical properties of these fluorophores was studied by fluorescence emission spectra and DFT/TDDFT calculations. Fluorescence lifetime's were also measured in different solvents. All of our findings revealed the delicate interplay of structure and emission properties and thus having broader general utility. As the CT to LE intensity ratio can be employed as a sensing index, the dual emissive fluorophore can be utilized in designing the molecular recognition system too. We envisage that our investigation is of importance for the development of new fluorophores with predetermined photophysical properties that may find a wide range of applications in chemistry, biology, and material sciences.
• Cu(II)-anchored functionalized mesoporous SBA-15: An efficient and recyclable catalyst for the one-pot Click reaction in water
  作者：Susmita Roy、Tanmay Chatterjee、Malay Pramanik、Anupam Singha Roy、Asim Bhaumik、Sk. Manirul Islam

  DOI：10.1016/j.molcata.2014.01.027

  日期：2014.5

  A new pyridine-imine functionalized mesoporus silica (SBA-15) has been synthesized through the Schiff-base condensation of 3-aminopropyl functionalized SBA-15 with 2-pyridinecarboxaldehyde followed by the grafting of Cu(II) onto it resulting a new Cu@Pylm-SBA-15 material. 20-hexagonally ordered mesophases of the material are analyzed by small-angle powder X-ray diffractions (PXRD) and transmission electron microscopic (TEM) image analyses. The Cu(ll)-anchored mesoporous material, Cu@PyIm-SBA-15 showed excellent catalytic activity towards the one pot click reaction between azides formed in situ from the corresponding amines and acetylenes in water at 0 C to room temperature resulting a wide variety of 1,4-disubstituted 1,2,3-triazoles. The catalyst has been recycled for five cycles without any appreciable loss of catalytic activity and also without any appreciable Cu-leaching, suggesting a future potential of this novel mesoporous catalyst for the synthesis of 1,4-disubstituted 1,2,3-triazoles. (C) 2014 Elsevier B.V. All rights reserved.