[1-(4-硝基苯基)-5-苯基三唑-4-基]-苯基甲酮 | 122942-42-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: [1-(4-硝基苯基)-5-苯基三唑-4-基]-苯基甲酮
• 英文名称: (1-(4-nitrophenyl)-5-phenyl-1H-1,2,3-triazol-4-yl)(phenyl)methanone
• 英文别名: [1-(4-Nitrophenyl)-5-phenyl-1H-1,2,3-triazol-4-yl](phenyl)methanone；[1-(4-nitrophenyl)-5-phenyltriazol-4-yl]-phenylmethanone
• CAS: 122942-42-1
• 化学式: C₂₁H₁₄N₄O₃
• 分子量: 370.367
• InChiKey: HANGDAVQZCGNED-UHFFFAOYSA-N

物化性质

• 沸点：
  640.1±65.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  93.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-nitrophenyl azide 、 二苯甲酰基甲烷 在 水 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 反应 1.17h， 以87%的产率得到[1-(4-硝基苯基)-5-苯基三唑-4-基]-苯基甲酮
  参考文献：
  名称：

  Synthesis of biologically as well as industrially important 1,4,5-trisubstituted-1,2,3-triazoles using a highly efficient, green and recyclable DBU–H2O catalytic system

  摘要：

  取代的1,2,3-呫唑是重要的杂环分子，在多个研究领域具有应用。叠氮化物与可烯醇化合物的1,3-极性环加成反应是一种生成取代1,2,3-呫唑的重要方法。然而，文献中报道的芳香叠氮化物的1,3-环加成方法涉及较长的反应时间、使用危险/挥发性试剂以及有毒的有机溶剂。在本文中，我们报道了通过在DBU-水体系中对各种芳香叠氮化物与活性亚甲基化合物进行反应，合成1,4,5-三取代-1,2,3-呫唑的新型环保合成方法，反应条件为传统加热、超声波和微波照射。这里定义的方法在合成上具有高原子经济、低环境影响、温和反应条件以及在较短反应时间内获得良好产率和反应介质的可回收性等优点。

  DOI：

  10.1039/c3ra44440f

文献信息

• A combined experimental and theoretical study of the thermal cycloaddition of aryl azides with activated alkenes
  作者：Sarah Zeghada、Ghenia Bentabed-Ababsa、Aïcha Derdour、Safer Abdelmounim、Luis R. Domingo、José A. Sáez、Thierry Roisnel、Ekhlass Nassar、Florence Mongin

  DOI：10.1039/c1ob05176h

  日期：——

  β-dicarbonyl compounds with their enol forms, a 1,3-dipolar cycloaddition of the enol forms with the aryl azides (high activation energy), and a dehydration process (lower activation energy). The effect of non-conventional activation methods on the degradation of 1,2,3-triazolines was next studied experimentally. Finally, some of the 1,2,3-triazoles such synthesized were evaluated for their bactericidal and

  一方面是由芳基叠氮化物进行反应，另一方面是由β-二羰基化合物或丙二腈衍生的活化烯烃，通过常规加热或微波活化，得到1-芳基-1 H-1,2,3-三唑 理论上已经使用DFT方法在B3LYP / 6-31G *水平上研究了涉及β-二羰基化合物的反应机理和区域选择性：它们是包含β-二羰基化合物及其烯醇形式的互变异构平衡的多米诺过程。烯醇的1，3-偶极环加成与芳基叠氮化物（高活化能）和脱水过程（较低活化能）形成。接下来通过实验研究非常规活化方法对1,2,3-三唑啉降解的影响。最后，评估了这样合成的一些1,2,3-三唑的杀菌和细胞毒性活性。
• Catalytic behavior of surfactant-containing-MCM-41 mesoporous materials for cycloaddition of 4-nitrophenyl azide
  作者：Bouhadjar Boukoussa、Sarah Zeghada、Ghenia Bentabed Ababsa、Rachida Hamacha、Aïcha Derdour、Abdelkader Bengueddach、Florence Mongin

  DOI：10.1016/j.apcata.2014.10.022

  日期：2015.1

  Si-MCM-41, Ga-MCM-41 and Al-MCM-41 mesoporous catalysts (with Si/Al = 80 and Si/Ga = 80) were prepared by direct synthesis under hydrothermal crystallization method using sodium aluminate or gallium sulfate and tetraethyl orthosilicate (TEOS) as aluminum or gallium and silica sources, respectively. The structural features of the materials were determined by various physico-chemical techniques such as X-ray diffraction (XRD), nitrogen sorption at 77K, Fourier transform infrared spectroscopy (FTIR), scanning and transmission electronic microscopy (SEM, TEM) and thermogravimetric analysis ATG. The catalytic activity of the calcined and as-synthesized catalyst was evaluated through the cycloaddition reaction of 4-nitrophenyl azide with activated alkenes at room temperature under liquid-phase conditions. High yields of 1,2,3-triazole were obtained. For comparison purpose, mixtures of homogeneous and heterogeneous catalyst Et3N/M-MCM-41 (M = Al or Ga) are also tested. The catalyst was used in five consecutive experiments without important loss of activity, confirming its stability. Finally, a new method for preparing triazoles in short reaction times was developed. (C) 2014 Elsevier B.V. All rights reserved.
• Benati, Luisa; Montevecchi, P. Carlo; Spagnolo, Piero, Gazzetta Chimica Italiana, 1992, vol. 122, # 5-7, p. 249 - 251
  作者：Benati, Luisa、Montevecchi, P. Carlo、Spagnolo, Piero

  DOI：——

  日期：——
• Fouli, Fouli Abd El-Rahim; Shaban, Mohamed El-Badry; El-Nagdy, El-Sayed Ibrahim, Acta Chimica Hungarica, 1988, vol. 125, # 6, p. 785 - 792
  作者：Fouli, Fouli Abd El-Rahim、Shaban, Mohamed El-Badry、El-Nagdy, El-Sayed Ibrahim、Youssef, Ahmed Said Ahmed

  DOI：——

  日期：——