2-(4-(phenoxymethyl)-1H-1,2,3-triazol-1-yl)-1-phenylethanone | 1407485-57-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(4-(phenoxymethyl)-1H-1,2,3-triazol-1-yl)-1-phenylethanone
• 英文别名: 2-(4-(Phenoxy methyl)-1h-1,2,3-triazol-1-yl)-1-phenyl-ethanone；2-[4-(phenoxymethyl)triazol-1-yl]-1-phenylethanone
• CAS: 1407485-57-7
• 化学式: C₁₇H₁₅N₃O₂
• 分子量: 293.325
• InChiKey: VQYWVJNGWMNYRG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  57
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  苯酚 在 sodium azide 、 铜 、 potassium carbonate 作用下， 以 水 、 丙酮 为溶剂， 反应 17.0h， 生成 2-(4-(phenoxymethyl)-1H-1,2,3-triazol-1-yl)-1-phenylethanone
  参考文献：
  名称：

  均匀的铜纳米颗粒，作为一种廉价高效的催化剂，可在水介质中合成新型β-羰基-1，2，3-三唑

  摘要：

  通过球磨制备铜纳米颗粒，作为一种有效，廉价的催化剂，用于在水中通过点击反应从叠氮醇合成β-羰基1、2、3-三唑。使用了多种原材料，例如叠氮化钠，苯甲酰溴，表氯醇和末端炔烃。在室温下，通过球磨与球粉重量比为50：1的球磨，可以完成NaBH 4存在下的CuO的完全还原。通过SEM，EDX，XRD和FT-IR对最终的铜纳米颗粒（Cu NPs）进行了表征。Cu NPs在室温下以短反应时间和高收率催化了β-羰基1、2、3-三唑的一锅三组分合成。该催化剂可以容易地回收并在几个连续的运行中重复使用。

  DOI：

  10.1007/s11164-019-03773-9

文献信息

• Copper(II) Schiff Base Complexes with Catalyst Property: Experimental, Theoretical, Thermodynamic and Biological Studies
  作者：Sheida Esmaielzadeh、Elham Zarenezhad

  DOI：10.17344/acsi.2018.4159

  日期：2018.6.20

  conclusion obtained by the experimental studies. Thermodynamic study of complex formation in solution was carried out spectrophotometrically at 25 °C. These compounds were also subjected to study in vitro antibacterial screening against some bacteria. Also, click reaction was investigated for its catalytic properties. The synthesized Schiff base copper complexes catalyzed 1,3-dipolar Huisgen cycloaddition

  合成了两种新颖的席夫铜（II）席夫碱配合物，并通过各种物理化学和光谱方法进行了表征，揭示了铜原子周围扭曲的正方形平面几何形状。分析数据证实了配合物的金属对配体的化学计量比为1：1。B3LYP /（LANL2DZ / 6-311G **）密度泛函理论（DFT）用于研究合成化合物在气相中的结构和电子性质。计算结果支持了实验研究得出的结论。在25°C分光光度法进行了溶液中络合物形成的热力学研究。还对这些化合物进行了针对某些细菌的体外抗菌筛选研究。另外，还研究了点击反应的催化性能。
• Copper Schiff base complex as a new immobilized heterogeneous catalyst: experimental, theoretical, biological and docking study
  作者：Elham Zarenezhad、Sheida Esmaielzadeh、Somayeh Behrouz、Leila Emami

  DOI：10.1007/s13738-020-02024-8

  日期：2021.2

  Abstract The novel copper(II) Schiff base complex was synthesized. Density functional theory calculations at the B3LYP (6-311G**/LANL2DZ) level of theory have been carried out to investigate the structure and geometry of the Schiff base ligand and its copper complex. IR spectra data (experimental and theoretical) show that the ligand Schiff base is coordinated to the copper ion in a bi-negative tetradentate

  摘要 合成了新型铜（II）席夫碱配合物。已经进行了B3LYP（6-311G ** / LANL2DZ）理论水平的密度泛函理论计算，以研究席夫碱配体及其铜配合物的结构和几何形状。红外光谱数据（实验和理论数据）表明，配体席夫碱以双负四齿方式与NNOS供体位点与铜离子配位。从理论数据来看，发现该复合物的几何结构是扭曲的正方形平面。接下来，描述了通过将[CuL]固定在二氧化硅上来合成1、2、3-三唑衍生物的安全，有效和改进的方法。在新型铜（I）的存在下，末端炔烃与有机叠氮化物反应通过在室温下于H 2 O / THF中原位还原铜（II） Schiff碱与抗坏血酸的催化剂制备。而且，固定在二氧化硅上的[CuL]被批准为化学和热稳定的催化剂，可以重复使用多次，而催化活性没有明显损失。研究了标题化合物对白色念珠菌（ATCC 10231），克鲁斯念珠菌（ATCC 6258）和黑曲霉（ATCC 16404）的
• Inhibition of NaV1.6 sodium channel currents by a novel series of 1,4-disubstituted-triazole derivatives obtained via copper-catalyzed click chemistry
  作者：Mirko Rivara、Manoj K. Patel、Laura Amori、Valentina Zuliani

  DOI：10.1016/j.bmcl.2012.08.067

  日期：2012.10

  We have synthesized and evaluated a series of 1,4-disubstituted-triazole derivatives for inhibition of the rat Na(V)1.6 sodium channel isoform, an isoform thought to play an important role in controlling neuronal firing. Starting from a series of 2,4(1H)-diarylimidazoles previously published, we decided to extend the SAR study by replacing the imidazole with a different heterocyclic scaffold and by varying the aryl substituents on the central aromatic ring. The 1,4-disubstituted 1,2,3-triazoles were prepared employing the copper-catalyzed azide-alkyne cycloaddition (CuAAC). Many of the new molecules were able to block the rNa(V)1.6 currents at 10 mu M by over 20%, displaying IC50 values ranging in the low micromolar, thus indicating that triazole can efficiently replace the central heterocyclic core. Moreover, the introduction of a long chain at C4 of the central triazole seems beneficial for increased rNa(V)1.6 current block, whereas the length of N1 substituent seems less crucial for inhibition, as long as a phenyl ring is not direcly connected to the triazole. These results provide additional information on the structural features necessary for block of the voltage-gated sodium channels. These new data will be exploited in the preparation of new compounds and could result in potentially useful AEDs. (c) 2012 Elsevier Ltd. All rights reserved.
• Uniform copper nanoparticles as an inexpensive and efficient catalyst for synthesis of novel β-carbonyl-1, 2, 3-triazoles in water medium
  作者：Hadi Esmaeili-Shahri、Hossein Eshghi、Jalil Lari、Seyyed Amin Rounaghi、Effat Esmaeili-Shahri

  DOI：10.1007/s11164-019-03773-9

  日期：2019.5

  prepared via ball milling for synthesis of β-carbonyl 1, 2, 3-triazoles from azido alcohol by click reaction in water. An extensive range of raw materials such as sodium azide, phenacyl bromide, epichlorohydrin, and terminal alkynes were used. Complete reduction of CuO in presence of NaBH4 was done via ball milling with a ball-to-powder weight ratio of 50:1 under air atmosphere at room temperature. The

  通过球磨制备铜纳米颗粒，作为一种有效，廉价的催化剂，用于在水中通过点击反应从叠氮醇合成β-羰基1、2、3-三唑。使用了多种原材料，例如叠氮化钠，苯甲酰溴，表氯醇和末端炔烃。在室温下，通过球磨与球粉重量比为50：1的球磨，可以完成NaBH 4存在下的CuO的完全还原。通过SEM，EDX，XRD和FT-IR对最终的铜纳米颗粒（Cu NPs）进行了表征。Cu NPs在室温下以短反应时间和高收率催化了β-羰基1、2、3-三唑的一锅三组分合成。该催化剂可以容易地回收并在几个连续的运行中重复使用。