1-phenethyl-4-p-tolyl-1H-1,2,3-triazole | 1379835-88-7

• 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-phenethyl-4-p-tolyl-1H-1,2,3-triazole
• 英文别名: 1-(2-phenethyl)-4-p-tolyl-1H-[1,2,3]triazole；1-(β-phenylethyl)-4-(p-methylphenyl)-1,2,3-triazole；4-(4-Methylphenyl)-1-(2-phenylethyl)triazole；4-(4-methylphenyl)-1-(2-phenylethyl)triazole
• CAS: 1379835-88-7
• 化学式: C₁₇H₁₇N₃
• 分子量: 263.342
• InChiKey: VPGSTVJLJLQHDD-UHFFFAOYSA-N

物化性质

• 沸点：
  451.5±53.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  30.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-phenethyl-4-p-tolyl-1H-1,2,3-triazole 、 3-phenyl-1,4,2-dioxazol-5-one 在 silver hexafluoroantimonate 、 carbonyl(pentamethylcyclopentadienyl)cobalt diiodide 、 potassium acetate 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 24.0h， 以60%的产率得到N-(5-methyl-2-(1-phenethyl-1H-1,2,3-triazol-4-yl)phenyl)benzamide
  参考文献：
  名称：

  Cobalt-catalyzed amination of triazoles with dioxazol-5-ones through triazole-directed ortho C H activation

  摘要：

  Cobalt-catalyzed reactions of triazoles and dioxazol-5-one involving nitrene transfer were described. A number of amidated 1,2,3-trizole derivatives have been obtained in moderate to excellent yields. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2016.10.032
• 作为产物：
  描述：

  乙基溴苯 在 sodium azide 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.17h， 生成 1-phenethyl-4-p-tolyl-1H-1,2,3-triazole
  参考文献：
  名称：

  Rational modifications on a benzylidene-acrylohydrazide antiviral scaffold, synthesis and evaluation of bioactivity against Chikungunya virus

  摘要：

  Chikungunya virus is a re-emerging arbovirus transmitted to humans by Aedes mosquitoes, responsible for an acute febrile illness associated with painful and debilitating arthralgia, which can persist for several months or become chronic. Over the past few years, infection with this virus has spread worldwide with a previously unknown virulence. No specific antiviral treatments nor vaccines are currently available against this important pathogen. Starting from the structure of a class of selective anti-CHIKV agents previously identified in our research group, different modifications to this scaffold were rationally designed, and 69 novel small-molecule derivatives were synthesised and evaluated for their inhibition of Chikungunya virus replication in Vero cells. Further structure-activity relationships associated with this class of antiviral agents were elucidated for the original scaffolds, and novel antiviral compounds with EC50 values in the low micromolar range were identified. This work provides the foundation for further investigation of these new structures as antivirals against Chikungunya virus. (C) 2018 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2018.02.054

文献信息

• Bio-waste corn-cob cellulose supported poly(hydroxamic acid) copper complex for Huisgen reaction: Waste to wealth approach
  作者：Bablu Hira Mandal、Md. Lutfor Rahman、Mashitah Mohd Yusoff、Kwok Feng Chong、Shaheen M. Sarkar

  DOI：10.1016/j.carbpol.2016.09.021

  日期：2017.1

  azides with a variety of alkynes as well as one-pot three-components reaction in the presence of sodium ascorbate to give the corresponding cycloaddition products in up to 96% yield and high turn over number (TON 18,600) and turn over frequency (TOF 930h-1) were achieved. The complex was easy to recover from the reaction mixture and reused six times without significant loss of its catalytic activity.

  玉米芯纤维负载的聚（异羟肟酸）Cu（II）配合物是通过废玉米芯纤维的表面改性通过接枝共聚和随后的加氢氧化制得的。通过IR，UV，FESEM，TEM，XPS，EDX和ICP-AES分析对络合物进行表征。已发现该络合物是一种有效的催化剂，可在各种抗坏血酸钠存在下，与多种炔烃进行芳基/烷基叠氮化物的1，3-偶极惠斯根环加成反应（CuAAC）以及一锅三组分反应，从而生成相应的环加成产物的收率高达96％，并且具有较高的周转率（TON 18,600）和周转频率（TOF 930h-1）。该配合物易于从反应混合物中回收，并且可以重复使用六次，而不会显着降低其催化活性。
• Amphiphilic Self-Assembled Polymeric Copper Catalyst to Parts per Million Levels: Click Chemistry
  作者：Yoichi M. A. Yamada、Shaheen M. Sarkar、Yasuhiro Uozumi

  DOI：10.1021/ja3036543

  日期：2012.6.6

  Self-assembly of copper sulfate and a poly(imidazole-acrylamide) amphiphile provided a highly active, reusable, globular, solid-phase catalyst for click chemistry. The self-assembled polymeric Cu catalyst was readily prepared from poly(N-isopropylacrylamide-co-N-vinylimidazole) and CuSO(4) via coordinative convolution. The surface of the catalyst was covered with globular particles tens of nanometers

  硫酸铜和聚（咪唑-丙烯酰胺）两亲物的自组装为点击化学提供了一种高活性、可重复使用的球状固相催化剂。自组装聚合铜催化剂很容易通过配位卷积由聚 (N-异丙基丙烯酰胺-co-N-乙烯基咪唑) 和 CuSO(4) 制备。催化剂表面覆盖着直径为数十纳米的球状颗粒，这些片状复合材料层层叠叠，形成聚集结构。此外，聚合物配体中的咪唑单元与 CuSO(4) 协调，以提供自组装、分层、聚合的铜配合物。甚至 4.5-45 mol ppm 的不溶性两亲聚合咪唑 Cu 催化剂驱动了 Huisgen 1,3-偶极环加成各种炔烃和有机叠氮化物，包括各种炔烃、有机卤化物和叠氮化钠的三组分环化。催化营业额数和频率分别高达 209000 和 6740 h(-1)。该催化剂易于重复使用而不会损失催化活性以定量得到相应的三唑。
• Poly(hydroxamic acid) functionalized copper catalyzed C–N bond formation reactions
  作者：Md. Shaharul Islam、Bablu Hira Mandal、Tapan Kumar Biswas、Md. Lutfor Rahman、S. S. Rashid、Suat-Hian Tan、Shaheen M. Sarkar

  DOI：10.1039/c6ra08155j

  日期：——

  Highly active poly(hydroxamic acid) functionalized copper catalysts were synthesized by the surface modification of khaya cellulose through graft copolymerization and subsequent hydroximation processes. The prepared catalysts were well characterized by FTIR, FESEM, HRTEM, ICP-AES, UV-vis and XPS analyses. The supported catalysts effectively promoted C–N bond formation reactions and provided excellent

  通过接枝共聚和随后的加氢脱氧过程对khaya纤维素进行表面改性，合成了高活性的聚（异羟肟酸）官能化铜催化剂。FTIR，FESEM，HRTEM，ICP-AES，UV-vis和XPS分析对制备的催化剂进行了很好的表征。在温和的反应条件下，负载型催化剂有效地促进了C–N键的形成反应，并提供了优异的产率。催化剂易于从反应混合物中回收，并且可以重复使用数次，而其催化活性没有任何重大损失。
• 一种三氮唑衍生物及其制备方法
  申请人：浙江大学

  公开号：CN108395412A

  公开（公告）日：2018-08-14

  本发明公开了一种三氮唑衍生物，其结构式如式(I)或式(II)所示；本发明还提供了所述三氮唑衍生物的制备方法，包括：在有机溶剂中，在催化剂和添加剂的共同作用下，1,2,3‑三唑衍生物与重氮化合物进行反应，反应完成后，经后处理得到结构式如式(I)或式(II)所示的三氮唑衍生物。本发明提供的制备方法操作简单、易行，原料廉价易得，可用于合成一系列三氮唑衍生物，对探索复杂三氮唑衍生物的合成具有重要的应用价值。
• Rhodium-catalyzed triazole-directed C–H bond functionalization of arenes with diazo compounds
  作者：Huanhong Wang、Xiaofei Yi、Yanli Cui、Wanzhi Chen

  DOI：10.1039/c8ob01673a

  日期：——

  science. In this paper, rhodium(III)-catalyzed triazole-directed alkylation reactions of arenes using diazo compounds as the alkylating agents are described. A number of polysubstituted arenes were provided from easily available materials in good yields under mild conditions. The reactions proceed via triazole-directed ortho C–H bond activation and subsequent carbene insertion originating from diazo

  带有1,2,3-三唑支架的杂环化合物在药物化学和材料科学中都得到了广泛的应用。在本文中，描述了使用重氮化合物作为烷基化剂的铑（III）催化的芳烃的三唑定向烷基化反应。在温和的条件下，从容易获得的材料中以高收率提供了许多多取代的芳烃。反应是通过三唑定向的邻位C–H键活化和随后由重氮化合物引起的卡宾插入而进行的。