4-(4-fluorophenyl)-2-phenyl-2H-1,2,3-triazole | 915727-99-0

• 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-fluorophenyl)-2-phenyl-2H-1,2,3-triazole
• 英文别名: 4-(4-Fluorophenyl)-2-phenyltriazole
• CAS: 915727-99-0
• 化学式: C₁₄H₁₀FN₃
• 分子量: 239.252
• InChiKey: QRXUIHUPBPFPIX-UHFFFAOYSA-N

物化性质

• 熔点：
  100-101 °C
• 沸点：
  410.7±37.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  30.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(4-fluorophenyl)-2-phenyl-2H-1,2,3-triazole 在 氯磺酸 、 sodium chloride 作用下， 生成 4-[4-(4-Fluoro-phenyl)-[1,2,3]triazol-2-yl]-benzenesulfonyl chloride
  参考文献：
  名称：

  Human β3-adrenergic receptor agonists containing 1,2,3-triazole-substituted benzenesulfonamides

  摘要：

  Compounds containing a 1,2,3-triazole-substituted benzenesulfonamide were prepared and found to be potent and selective human beta(3)-adrenergic receptor agonists. The most interesting compound, trifluoromethylbenzyl analogue 12e (beta(3) EC50 = 3.1 nM with >1500-fold selectivity over binding to both beta(1)- and beta(2) receptors), stimulates lipolysis in the rhesus monkey (ED50 = 0.36 mg/kg) and is 25% orally bioavailable in the dog. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00422-4
• 作为产物：
  描述：

  2,2-二溴-4’-氟苯乙酮 在 copper dichloride 作用下， 以 乙醇 、 溶剂黄146 为溶剂， 反应 5.0h， 生成 4-(4-fluorophenyl)-2-phenyl-2H-1,2,3-triazole
  参考文献：
  名称：

  Arora, Loveena; Sharma, Nisha; Kapoor, Jitander K., Indian Journal of Heterocyclic Chemistry, 2016, vol. 25, # 3-4, p. 291 - 296

  摘要：

  DOI：

文献信息

• N-2-Aryl-1,2,3-triazoles: A Novel Class of UV/Blue-Light-Emitting Fluorophores with Tunable Optical Properties
  作者：Wuming Yan、Qiaoyi Wang、Quan Lin、Minyong Li、Jeffrey L. Petersen、Xiaodong Shi

  DOI：10.1002/chem.201002937

  日期：2011.4.26

  new class of UV/blue‐light‐emitting fluorophores. Though both N‐1‐aryl‐1,2,3‐triazoles and N‐2‐aryl‐1,2,3‐triazoles gave strong photo absorption under excitation at 330 nm, only the N‐2‐analogous showed strong fluorescence emission in the UV/blue range with high efficiency in various solvents (quantum yield Φ around 0.3–0.5). Significant substituted group effects were observed, allowing tunable optical

  N-2-芳基-1,2,3-三唑衍生物（NATs）被开发为一类新的发出UV /蓝光的荧光团。尽管N-1-芳基1,2,3-三唑和N-2-芳基1,2,3-三唑在330 nm激发下均具有很强的光吸收能力，但只有N-2类似物显示出很强的荧光发射在紫外/蓝光范围内，在各种溶剂中均具有较高的效率（量子产率Φ约为0.3-0.5）。观察到了显着的取代基效应，使发射的光学特性可调（最大λ）从350-400 nm范围变化，斯托克斯（Stokes）从38-93 nm范围变化。计算研究以及X射线晶体结构表明了三唑环与N-2位置上的芳基之间有效共轭的重要性。提出了平面分子内电荷转移（PICT）机理，并得到溶剂效应研究的支持。简单衍生得到NAT-修饰的赖氨酸和强UV /蓝色发光二NAT（Φ= 0.76，λ最大= 390），这表明在生物和材料科学的研究这种新的类荧光团的巨大潜力。
• Simple and Efficient One‐Pot Synthesis of 2,4‐Diaryl‐1,2,3‐triazoles
  作者：Wen‐Jie Tang、Yong‐Zhou Hu

  DOI：10.1080/00397910600781216

  日期：2006.8.1

  Abstract A general and efficient method for the preparation of 2,4‐diaryl‐1,2,3‐triazoles from α‐hydroxyacetophenones and phenylhydrazines is reported. The essential characteristics of this method include mild reaction conditions, a straightforward workup procedure, and comparatively higher yields.

  摘要 报道了一种从 α-羟基苯乙酮和苯肼制备 2,4-二芳基-1,2,3-三唑的通用且有效的方法。这种方法的基本特征包括温和的反应条件、简单的后处理程序和相对较高的收率。
• Catalyst-Free Regioselective N² Arylation of 1,2,3-Triazoles Using Diaryl Iodonium Salts
  作者：Sahar Roshandel、Maiko J. Lunn、Golam Rasul、Daniel Sylvinson Muthiah Ravinson、Suresh C. Suri、G. K. Surya Prakash

  DOI：10.1021/acs.orglett.9b02140

  日期：2019.8.16

  The widespread application of 1,2,3-triazoles in pharmaceuticals has resulted in substantial interest toward developing efficient postmodification methods. Whereas there are many postmodification methods available to obtain N-1-substituted 1,2,3-triazoles, developing a selective and convenient protocol to synthesize N-2-aryl-1,2,3-triazoles has been challenging. We report a catalyst-free and regioselective method to access N-2-aryl-1,2,3-triazoles in good to excellent yields (66-97%). This scalable postmodification protocol is effective for a wide range of substrates.
• Arora, Loveena; Sharma, Nisha; Kapoor, Jitander K., Indian Journal of Heterocyclic Chemistry, 2016, vol. 25, # 3-4, p. 291 - 296
  作者：Arora, Loveena、Sharma, Nisha、Kapoor, Jitander K.

  DOI：——

  日期：——
• Human β3-adrenergic receptor agonists containing 1,2,3-triazole-substituted benzenesulfonamides
  作者：Linda L Brockunier、Emma R Parmee、Hyun O Ok、Mari R Candelore、Margaret A Cascieri、Lawrence F Colwell、Liping Deng、William P Feeney、Michael J Forrest、Gary J Hom、D.Euan MacIntyre、Laurie Tota、Matthew J Wyvratt、Michael H Fisher、Ann E Weber

  DOI：10.1016/s0960-894x(00)00422-4

  日期：2000.9

  Compounds containing a 1,2,3-triazole-substituted benzenesulfonamide were prepared and found to be potent and selective human beta(3)-adrenergic receptor agonists. The most interesting compound, trifluoromethylbenzyl analogue 12e (beta(3) EC50 = 3.1 nM with >1500-fold selectivity over binding to both beta(1)- and beta(2) receptors), stimulates lipolysis in the rhesus monkey (ED50 = 0.36 mg/kg) and is 25% orally bioavailable in the dog. (C) 2000 Elsevier Science Ltd. All rights reserved.