4-{[4-(4-methoxyphenyl)-1H-1,2,3-triazol-1-yl]methyl}benzonitrile | 1511858-48-2

• 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-(4-methoxyphenyl)-1H-1,2,3-triazol-1-yl]methyl}benzonitrile
• 英文别名: 4-[[4-(4-Methoxyphenyl)triazol-1-yl]methyl]benzonitrile
• CAS: 1511858-48-2
• 化学式: C₁₇H₁₄N₄O
• 分子量: 290.324
• InChiKey: DJHQGXRQIUOEDQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.87
• 重原子数：
  22.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  63.73
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  对氰基溴化苄 、 4-乙炔基苯甲醚 在 sodium azide 作用下， 以 水 为溶剂， 反应 0.33h， 以93%的产率得到4-{[4-(4-methoxyphenyl)-1H-1,2,3-triazol-1-yl]methyl}benzonitrile
  参考文献：
  名称：

  新型铜标记负载离子液相催化剂用于铜催化水中叠氮化物-炔烃环加成反应合成 1,4-二取代 1,2,3-三唑

  摘要：

  本手稿探讨了新型抗坏血酸功能化铜标记聚合物负载离子液相催化剂 (PSILPC) 的设计、合成和应用。采用FT-IR、XRD、SEM、TEM、EDS、XPS和ICP-AES等多种物理化学技术对新合成的SILP催化剂进行了表征。研究了合成的 SILP 催化剂对烷基或芳基卤化物、叠氮化钠和末端炔烃的铜催化叠氮化物-炔烃环加成 (CuAAC) 的催化性能，从而提供了一系列 1,4-二取代-1,2,3-三唑优良的产量。该协议描述了诸如使用水作为生态良性溶剂、从芳基/烷基卤化物原位生成叠氮化物、优异的产率、温和的反应条件、简单的后处理、更短的反应时间、高周转次数和高周转频率等优点. 图形概要

  DOI：

  10.1007/s10562-021-03898-w

文献信息

• Stoichiometric sensitivity and structural diversity in click-active copper(<scp>i</scp>) N,S-heterocyclic carbene complexes
  作者：Xiaoyan Han、Zhiqiang Weng、David James Young、Guo-Xin Jin、T. S. Andy Hor

  DOI：10.1039/c3dt52059e

  日期：——

  A series of novel Cu(I) N,S-heterocyclic carbene (NSHC) complexes [Cu(μ-Br)(NSHC)]2, [Cu(μ-X)(NSHC)]4 (X = Br or I), [(NSHC)2Cu(μ-Br)2Cu(NSHC)], and [(NSHC)2CuBr] have been isolated from in situ generated CuOtBu and N-substituted benzothiazolium halides and characterized by X-ray crystallography. Five structural motifs were observed, viz. MxLy where x : y = 2 : 2, 4 : 4, 2 : 3, 1 : 2 and 2 : 4, with

  一系列新颖的Cu（I）N，S-杂环卡宾（NSHC）配合物[Cu（μ-Br）（NSHC）] 2，[Cu（μ-X）（NSHC）] 4（X = Br或I） ，[（NSHC）2 Cu（μ-Br）2 Cu（NSHC）]和[（NSHC）2 CuBr]已从原位生成的CuO t Bu和N-取代的苯并噻唑鎓卤化物中分离出来，并通过X射线晶体学表征。观察到五个结构基序，即。M x L y其中x  ：  y= 2：2、4：4、2：3、1：2和2：4，Cu⋯Cu的间距跨度范围为2.5626（7）至3.4725（7）Å。对这些化合物的催化活性的初步研究表明，不寻常的单核络合物6 [（NSHC）2 CuBr]是叠氮化物和炔烃的Huisgen 1,3-偶极环加成反应的活性催化剂，而络合物1-5和7则微不足道。不太活跃。
• A Copper(I)-Mediated Tandem Three-Component Synthesis of 5-Allyl-1,2,3-triazoles
  作者：Yoona Song、Soyun Lee、Palash Dutta、Jae-Sang Ryu

  DOI：10.1055/s-0039-1691506

  日期：2020.3

  A copper(I)-mediated tandem three-component reaction using alkynes, azides, allyl iodides, CuI and NaNH2 is developed. The reactions proceed smoothly at room temperature to afford 5-allyl-1,2,3-triazoles, which can be further converted into 1,2,3-triazole-fused tricyclic scaffolds. This method features an efficient one-pot cascade route using commercial alkynes and affords the corresponding 5-allyl-1

  开发了使用炔烃，叠氮化物，烯丙基碘，CuI和NaNH 2的铜（I）介导的串联三组分反应。反应在室温下平稳进行，得到5-烯丙基-1,2,3-三唑，其可以进一步转化为1,2,3-三唑稠合的三环支架。该方法的特点是使用商业炔烃的高效一锅级联途径，并在温和的反应条件下以高收率和良好的选择性提供了相应的5-烯丙基-1,2,3-三唑。
• Synthesis of magnetically separable catalyst Cu-ACP-Am-Fe3O4@SiO2 for Huisgen 1,3-dipolar cycloaddition
  作者：S.P. Vibhute、P.M. Mhaldar、S.N. Korade、D.S. Gaikwad、R.V. Shejawal、D.M. Pore

  DOI：10.1016/j.tetlet.2018.08.045

  日期：2018.10

  The present manuscript elicits the use of novel magnetically separable silica coated copper (Cu-ACP-Am-Fe3O4@SiO2) as a heterogeneous nanocatalyst for the Huisgen 1,3-dipolar cycloaddition reaction of alkyl or aryl halide, sodium azide and terminal alkyne, which provide a series of 1,4-disubstituted-1,2,3-triazoles. The catalyst was characterized by various physicochemical techniques such as Powder X-ray Diffraction (XRD), Fourier Transform Infrared Spectroscopy (FT-IR), Scanning Electron Microscopy (SEM), Transmission Electron Microscopy (TEM), Energy Dispersive X-Ray Spectroscopy(EDS), Thermogravimetric analysis (TGA-DSC), X-ray Photoelectron spectroscopy (XPS) and Vibrational sampling magnetometer (VSM). The acquisition of this nanocatalyst is also exemplified by employing reusability test and recycling of synthesized catalyst was achieved multiple times just by sequestering with an external magnet. It is noteworthy that the key-features like mild reaction conditions, simple work-up, High turnover number (TON), high turnover frequency (TOF), no use of hazardous organic solvents, easy recovery and reusability of the catalyst makes the present protocol more fascinating from an environmental and economic point of view. (C) 2018 Elsevier Ltd. All rights reserved.