1-benzyl-4-(naphthalene-2-yloxymethyl)-1H-[1,2,3]triazole | 1426533-49-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-benzyl-4-(naphthalene-2-yloxymethyl)-1H-[1,2,3]triazole
• 英文别名: 1-benzyl-4-((naphthalen-6-yloxy)methyl)-1H-1,2,3-triazole；1-benzyl-4-((naphthalen-2-yloxy)methyl)-1H-1,2,3-triazole；1-benzyl-4-((naphthalen-3-yloxy)methyl)-1H-1,2,3-triazole；1-benzyl-4-(naphthalen-2-yloxymethyl)triazole
• CAS: 1426533-49-4
• 化学式: C₂₀H₁₇N₃O
• 分子量: 315.374
• InChiKey: RSJNQJFHKGGWEM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 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：

  2-萘酚 在 copper(ll) sulfate pentahydrate 、 potassium carbonate 、 sodium ascorbate 作用下， 以 水 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 15.5h， 生成 1-benzyl-4-(naphthalene-2-yloxymethyl)-1H-[1,2,3]triazole
  参考文献：
  名称：

  Synthesis and evaluation of naphthyl bearing 1,2,3-triazole analogs as antiplasmodial agents, cytotoxicity and docking studies

  摘要：

  Novel series of naphthyl bearing 1,2,3-triazoles (4a-t) were synthesized and evaluated for their in vitro antiplasmodial activity against pyrimethamine (Pyr)-sensitive and resistant strains of Plasmodium falciparum. The synthesized compounds were assessed for their cytotoxicity employing human embryonic kidney cell line (HEK-293), and none of them was found to be toxic. Among them 4j, 4k, 4l, 4m, 4n, 4t exhibited significant antiplasmodial activity in both strains, of which compounds 4m, 4n and 4t (similar to 3.0fold) displayed superior activity to Pyr against resistant strain. Pyr and selected compounds (4n, 4p and 4t) that repressed parasite development also inhibited PfDHFR activity of the soluble parasite extract, suggesting that anti-parasitic activity of these compounds is a result of inhibition of the parasite DHFR. In silico studies suggest that activity of these compounds might be enhanced due to p-p stacking. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2016.10.029

文献信息

• Impregnated copper ferrite on mesoporous graphitic carbon nitride: An efficient and reusable catalyst for promoting ligand‐free click synthesis of diverse 1,2,3‐triazoles and tetrazoles
  作者：Dariush Khalili、Meysam Rezaee

  DOI：10.1002/aoc.5219

  日期：2019.11

  Magnetic CuFe2O4/g‐C3N4 hybrids were synthesized through a facile method and their catalytic performances were evaluated in click chemistry for the first time. The structural and morphological characterization of prepared materials was carried out by different techniques such as X‐ray diffraction, high‐resolution transmission electron microscopy, field emission scanning electron microscopy, Fourier

  通过简便的方法合成了磁性CuFe 2 O 4 / g-C 3 N 4杂化物，并首次在点击化学中评估了它们的催化性能。所制备材料的结构和形态表征是通过不同的技术进行的，例如X射线衍射，高分辨率透射电子显微镜，场发射扫描电子显微镜，傅立叶红外光谱，振动样品磁力分析，热重分析和N 2吸附–解吸分析（Brunauer-Emmett-Teller表面积）。磁性CuFe 2 O 4 / g‐C 3 N 4的利用率使用烷基卤和环氧化物作为叠氮化物前体，可在水中进行一锅叠氮化物-炔烃环加成反应中获得优异性能，而无需任何其他试剂。本系统的范围很广，对于大环三唑以及四唑的合成特别实用。此外，该催化系统具有便利的条件，特别是在低催化剂负载量下易于获得各种重要产品，并且易于操作和分离的方法，可高度满足“绿色点击化学”的要求。
• Dendrimer-encapsulated copper(II) immobilized on Fe3O4@SiO2 NPs: a robust recoverable catalyst for click synthesis of 1,2,3-triazole derivatives in water under mild conditions
  作者：Ali Reza Sardarian、Fattah Mohammadi、Mohsen Esmaeilpour

  DOI：10.1007/s11164-018-3672-x

  日期：2019.3

  In this paper, we have introduced Fe3O4@SiO2-dendrimer-encapsulated Cu(II) as a heterogeneous reusable catalyst for Cu-catalyzed azide-alkyne cycloaddition (CuAAC) reaction in good to excellent yields at ambient temperature in water without requiring ligands, reducing agents and bases. This present methodology is a clean, and environmentally friendly approach that offers many advantages including excellent yields, operational simplicity, short reaction time, and absence of any tedious workup or purification. Moreover, of interesting features are the stability of the catalyst toward leaching and the possibility of catalyst recycling without any significant loss of activity. In this paper, we have introduced Fe3O4@SiO2-dendrimer-encapsulated Cu(II) as a heterogeneous reusable catalyst for Cu-catalyzed azide-alkyne cycloaddition reaction (CuAAC) in good to excellent yields at ambient temperature in water without requiring ligands, reducing agents and bases.

  本文中，我们介绍了Fe3O4@SiO2-树枝状聚合物包裹的铜(II)作为一种异相可再利用催化剂，用于在水相中室温下进行的铜催化的叠氮-炔环加成反应（CuAAC），无需使用配体、还原剂和碱，即可获得良好至优异的产率。目前的方法是一种清洁、环境友好的途径，具有许多优点，包括优异的产率、操作简便、反应时间短，且无需繁琐的后处理或纯化步骤。此外，该催化剂的一个有趣特性是其抗浸出稳定性以及催化剂回收时不显著损失活性的可能性。在本文中，我们介绍了 @SiO2-树枝状聚合物包裹的铜(II)作为一种异相可再利用催化剂，用于在水相中室温下进行的铜催化的叠氮-炔环加成反应（CuAAC），无需使用配体、还原剂和碱，即可获得良好至优异的产率。
• Copper Salt of 12-Tungstophosphoric Acid: An Efficient and Reusable Heteropoly Acid for the Click Chemistry
  作者：K. V. Purnima、D. Sreenu、N. Bhasker、K. Nagaiah、N. Lingaiah、B. V. Subba Reddy、J. S. Yadav

  DOI：10.1002/cjoc.201200939

  日期：2013.4

  catalytic amount of copper‐exchanged phosphotungstic acid (Cu‐TPA) in the presence of triethyl amine in DMF to afford substituted triazoles in good yields with high selectivity. Interestingly, the coupling of alkyl azide with alkyne proceeds readily at room temperature to furnish 1,2,3‐triazoles in excellent yields. The catalyst can be recovered and reused for three to four subsequent runs with a minimal

  在DMF中存在三乙胺的情况下，使用催化量的铜交换的磷钨酸（Cu-TPA）可实现烷基溴，叠氮化钠和炔烃的三组分偶联，从而以高收率和高选择性提供取代的三唑。有趣的是，烷基叠氮化物与炔烃的偶联在室温下容易进行，从而以优异的产率提供1,2,3-三唑。可以回收催化剂并将其再利用三到四个随后的运行，而活性降低得最少。铜改性杂多酸的使用使该过程简单，方便且对环境友好。