5-(4-fluorophenyl)-1-phenyl-1H-1,2,3-triazole | 1378976-15-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-(4-fluorophenyl)-1-phenyl-1H-1,2,3-triazole
• 英文别名: 5-(4-Fluorophenyl)-1-phenyltriazole
• CAS: 1378976-15-8
• 化学式: C₁₄H₁₀FN₃
• 分子量: 239.252
• InChiKey: MPYNJDRPRMNRAD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 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

• 作为产物：
  描述：

  对氟苯乙醇 在 硫酰氟 、 potassium tert-butylate 、 potassium carbonate 作用下， 以 二甲基亚砜 为溶剂， 反应 14.0h， 生成 5-(4-fluorophenyl)-1-phenyl-1H-1,2,3-triazole
  参考文献：
  名称：

  Transition-metal-free regioselective construction of 1,5-diaryl-1,2,3-triazoles through dehydrative cycloaddition of alcohols with aryl azides mediated by SO₂F₂

  摘要：

  开发了一种新颖、简单且实用的方法，用于高效、经济、具有区域选择性的合成高价值的1,5-二芳基-1,2,3-三唑。

  DOI：

  10.1039/c8cc09693g

文献信息

• A Metal-Free Multicomponent Cascade Reaction for the Regiospecific Synthesis of 1,5-Disubstituted 1,2,3-Triazoles
  作者：Guolin Cheng、Xiaobao Zeng、Jinhai Shen、Xuesong Wang、Xiuling Cui

  DOI：10.1002/anie.201307499

  日期：2013.12.9

  About specifics: A method for the regiospecific synthesis of the title compounds through an unprecedented Michael addition/deacylative diazo transfer/cyclization sequence has been established. The simple and practical method can be used for the modification of primary amines including chiral α‐amines. The process involves the formation three covalent bonds and the cleavage of two covalent bonds (see

  关于细节：已经建立了通过空前的迈克尔加成/去酰基重氮转移/环化序列进行区域特异性合成标题化合物的方法。简单实用的方法可用于伯胺（包括手性α-胺）的修饰。该过程涉及三个共价键的形成和两个共价键的裂解（参见方案，Ts = 4-甲苯磺酰基）。
• Discovery of a Robust and Efficient Homogeneous Silver(I) Catalyst for the Cycloaddition of Azides onto Terminal Alkynes
  作者：James McNulty、Kunal Keskar

  DOI：10.1002/ejoc.201200930

  日期：2012.10

  A highly efficient, chemically stable, and well-defined homogeneous silver(I) catalyst is reported for the cycloaddition of azides onto terminal alkynes (Ag-AAC reaction). The Ag-AAC reaction occurs at room temperature or with heating to deliver exclusively the corresponding 1,4-triazole. A pronounced ligand effect was discovered through systematic modification to the ligand structure resulting in

  据报道，一种高效、化学稳定且定义明确的均相银 (I) 催化剂用于叠氮化物在末端炔烃上的环加成反应（Ag-AAC 反应）。Ag-AAC 反应发生在室温下或加热以专门提供相应的 1,4-三唑。通过对配体结构进行系统修饰，发现了显着的配体效应，从而发现了用于该反应的化学稳定的活性催化剂。
• Ln[N(SiMe3)2]3-catalyzed cycloaddition of terminal alkynes to azides leading to 1,5-disubstituted 1,2,3-triazoles: new mechanistic features
  作者：Longcheng Hong、Weijia Lin、Fangjun Zhang、Ruiting Liu、Xigeng Zhou

  DOI：10.1039/c3cc42534g

  日期：——

  The first example of rare earth metal-catalyzed cycloaddition of terminal alkynes to azides resulting in the formation of 1,5-disubstituted 1,2,3-triazoles is described. Preliminary studies revealed that the present cycloaddition shows unprecedented mechanistic features involving a tandem anionic cascade cyclization and anti-addition across the CC triple bond.

  首例稀土金属催化的末端炔烃与叠氮化合物的环加成反应，生成1,5-二取代的1,2,3-三唑，已被报道。初步研究表明，这一环加成反应展现出前所未有的机理特征，涉及串联的阴离子级联环化和反式加成穿过碳碳三键。
• Rational Design of 4-Aryl-1,2,3-Triazoles for Indoleamine 2,3-Dioxygenase 1 Inhibition
  作者：Ute F. Röhrig、Somi Reddy Majjigapu、Aurélien Grosdidier、Sylvian Bron、Vincent Stroobant、Luc Pilotte、Didier Colau、Pierre Vogel、Benoît J. Van den Eynde、Vincent Zoete、Olivier Michielin

  DOI：10.1021/jm300260v

  日期：2012.6.14

  Indoleamine 2,3-dioxygenase 1 (IDO1) is an important therapeutic target treatment of diseases such as cancer that involve pathological immune escape. Starting from the scaffold of our previously discovered IDO1 inhibitor 4-phenyl-1,2,3-triazole, we used computational structure-based methods to design more potent ligands. This approach yielded highly efficient low molecular weight inhibitors, the most active being of nanomolar potency both in an enzymatic and in a cellular assay, while showing no cellular toxicity and a high selectivity for IDO1 over tryptophan 2,3-dioxygenase (TDO). A quantitative structure-activity relationship based on the electrostatic ligand-protein interactions in the docked binding modes and on the quantum chemically derived charges of the triazole ring demonstrated a good explanatory power for the observed activities.
• Transition-metal-free regioselective construction of 1,5-diaryl-1,2,3-triazoles through dehydrative cycloaddition of alcohols with aryl azides mediated by SO₂F₂
  作者：Xu Zhang、K. P. Rakesh、Hua-Li Qin

  DOI：10.1039/c8cc09693g

  日期：——

  A novel, simple and practical method for mild, efficient, cost-effective and regioselective synthesis of highly valuable 1,5-diaryl-1,2,3-triazoles was developed.

  开发了一种新颖、简单且实用的方法，用于高效、经济、具有区域选择性的合成高价值的1,5-二芳基-1,2,3-三唑。