1-(3,5-bis(trifluoromethyl)phenyl)-4-phenyl-1H-1,2,3-triazole | 1607788-94-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-(3,5-bis(trifluoromethyl)phenyl)-4-phenyl-1H-1,2,3-triazole
• 英文别名: 1-[3,5-Bis(trifluoromethyl)phenyl]-4-phenyltriazole；1-[3,5-bis(trifluoromethyl)phenyl]-4-phenyltriazole
• CAS: 1607788-94-2
• 化学式: C₁₆H₉F₆N₃
• 分子量: 357.258
• InChiKey: RJKLUBFUPKZIJZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  30.7
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1-(3,5-bis(trifluoromethyl)phenyl)-4-phenyl-1H-1,2,3-triazole 在 正丁基锂 、 二异丙胺 、 重水 作用下， 以 四氢呋喃 为溶剂， 生成 1-(3,5-bis(trifluoromethyl)phenyl-2,6-d₂)-4-phenyl-1H-1,2,3-triazole-5-d₁
  参考文献：
  名称：

  Lithiation‐Functionalisation of Triazoles Bearing Electron‐Withdrawing N ‐Substituents: Challenges and Solutions**

  摘要：

  AbstractThe regioselective lithiation of 1,2,3‐triazoles provides an opportunity to introduce additional functionality, however this simple functionalisation strategy using triazoles bearing electron‐withdrawing N‐substituents has not been investigated until now. Herein, we demonstrate that the lithiated triazole intermediates can readily decompose, even at −78 °C. In addition, lithiation‐deuteration studies reveal lithiation can take place competitively on both the triazole and the electron‐withdrawn aryl ring. Careful control of reaction conditions is therefore required to i) minimise decomposition pathways; and ii) facilitate regioselective functionalisation of the triazole.

  DOI：

  10.1002/ejoc.202201459
• 作为产物：
  描述：

  间二(三氟甲基)苯胺 在 盐酸 、 copper(II) sulfate 、 维生素 C 作用下， 以 水 、 乙腈 为溶剂， 反应 2.83h， 生成 1-(3,5-bis(trifluoromethyl)phenyl)-4-phenyl-1H-1,2,3-triazole
  参考文献：
  名称：

  Preliminary investigations into triazole derived androgen receptor antagonists

  摘要：

  A range of 1,4-substituted-1,2,3-N-phenyltriazoles were synthesized and evaluated as non-steroidal androgen receptor (AR) antagonists. The motivation for this study was to replace the N-phenyl amide portion of small molecule antiandrogens with a 1,2,3-triazole and determine effects, if any, on biological activity. The synthetic methodology presented herein is robust, high yielding and extremely rapid. Using this methodology a series of 17 N-aryl triazoles were synthesized from commercially available starting materials in less than 3 h. After preliminary biological screening at 20 and 40 mu M, the most promising three compounds were found to display IC50 values of 40-50 mu M against androgen dependent (LNCaP) cells and serve as a starting point for further structure-activity investigations. All compounds in this work were the focus of an in silico study to dock the compounds into the human androgen receptor ligand binding domain (hARLBD) and compare their predicted binding affinity with known antiandrogens. A comparison of receptor-ligand interactions for the wild type and T877A mutant AR revealed two novel polar interactions. One with Q738 of the wild type site and the second with the mutated A877 residue. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.03.018

文献信息

• Copper-γ-cyclodextrin complexes immobilized on hexagonal boron nitride as an efficient catalyst in the multicomponent synthesis of 1,2,3-triazoles
  作者：Ruifang Nie、Rui Sang、Xiaojun Ma、Yang Zheng、Xu Cheng、Weijian Li、Li Guo、Hui Jin、Yong Wu

  DOI：10.1016/j.jcat.2016.09.022

  日期：2016.12

  recoverable and reusable heterogeneous catalyst can be used in the click synthesis of 1,2,3-triazoles via a one-pot three-component reaction of boracic acid, terminal alkynes, and sodium azide at room temperature in water. FT-IR, XRD, SEM, XPS, TG, and ICP-AES techniques were used to characterize the catalyst. In general, this reaction, with the aid of this new catalyst, afforded the corresponding products

  首次制备了固定在六方氮化硼上的铜-γ-环糊精配合物（h [受电子邮件保护]γ[受电子邮件保护]（OAc）2）。这种可回收和可重复使用的非均相催化剂可在室温下于水中通过硼酸，末端炔烃和叠氮化钠的一锅式三组分反应用于1,2,3-三唑的点击合成。FT-IR，XRD，SEM，XPS，TG和ICP-AES技术用于表征催化剂。通常，在这种新型催化剂的帮助下，该反应得到具有良好产率和对官能团的优异耐受性的相应产物。
• Azide-Alkyne Cycloaddition (CuAAC) in Alkane Solvents Catalyzed by Fluorinated NHC Copper(I) Complex
  作者：Maxim A. Topchiy、Alexandra A. Ageshina、Pavel S. Gribanov、Salekh M. Masoud、Timur R. Akmalov、Sergey E. Nefedov、Sergey N. Osipov、Mikhail S. Nechaev、Andrey F. Asachenko

  DOI：10.1002/ejoc.201801538

  日期：2019.2.7

  A highly efficient and environmentally benign protocol for copper‐catalyzed alkyne–azide cycloaddition (CuAAC) in industrially important alkane solvents was developed. New (NHCF)CuI complex decorated with bulky group [(CF3)2(OiAm)C–] exhibited the best catalytic activity in the reactions of diversely substituted alkyne and azide substrates in alkane solvents.

  针对工业上重要的烷烃溶剂中的铜催化的炔-叠氮化物环加成（CuAAC），开发了一种高效且对环境无害的方案。新的（NHC F）Cu I络合物装饰有大体积基团[（CF 3）2（O i Am）C–]在烷烃溶剂中不同取代的炔烃和叠氮化物底物的反应中表现出最佳的催化活性。
• Indoles Rather than Triazoles from the Ruthenium Porphyrin-Catalyzed Reaction of Alkynes with Aryl Azides
  作者：Paolo Zardi、Andrea Savoldelli、Daniela Maria Carminati、Alessandro Caselli、Fabio Ragaini、Emma Gallo

  DOI：10.1021/cs5012712

  日期：2014.11.7

  An unprecedented reactivity of aryl azides toward alkynes is presented herein. The reaction performed well in the presence of 2 mol % of ruthenium porphyrin catalysts and afforded substituted indoles instead of triazoles. The procedure is particularly appealing for the synthesis of C3-functionalized indoles which bear EWG on the fragment coming from the azide. The method allowed the synthesis of 15 derivatives with yields up to 95%, high regioselectivity, and without requiring the time-consuming prefunctionalization of reagents and the addition of oxidants and/or additives.
• Preliminary investigations into triazole derived androgen receptor antagonists
  作者：Jarrad M. Altimari、Birunthi Niranjan、Gail P. Risbridger、Stephanie S. Schweiker、Anna E. Lohning、Luke C. Henderson

  DOI：10.1016/j.bmc.2014.03.018

  日期：2014.5

  A range of 1,4-substituted-1,2,3-N-phenyltriazoles were synthesized and evaluated as non-steroidal androgen receptor (AR) antagonists. The motivation for this study was to replace the N-phenyl amide portion of small molecule antiandrogens with a 1,2,3-triazole and determine effects, if any, on biological activity. The synthetic methodology presented herein is robust, high yielding and extremely rapid. Using this methodology a series of 17 N-aryl triazoles were synthesized from commercially available starting materials in less than 3 h. After preliminary biological screening at 20 and 40 mu M, the most promising three compounds were found to display IC50 values of 40-50 mu M against androgen dependent (LNCaP) cells and serve as a starting point for further structure-activity investigations. All compounds in this work were the focus of an in silico study to dock the compounds into the human androgen receptor ligand binding domain (hARLBD) and compare their predicted binding affinity with known antiandrogens. A comparison of receptor-ligand interactions for the wild type and T877A mutant AR revealed two novel polar interactions. One with Q738 of the wild type site and the second with the mutated A877 residue. (C) 2014 Elsevier Ltd. All rights reserved.
• Lithiation‐Functionalisation of Triazoles Bearing Electron‐Withdrawing <i>N</i> ‐Substituents: Challenges and Solutions**
  作者：Frances E. Bugden、Guy J. Clarkson、Mark D. Greenhalgh

  DOI：10.1002/ejoc.202201459

  日期：2023.2

  AbstractThe regioselective lithiation of 1,2,3‐triazoles provides an opportunity to introduce additional functionality, however this simple functionalisation strategy using triazoles bearing electron‐withdrawing N‐substituents has not been investigated until now. Herein, we demonstrate that the lithiated triazole intermediates can readily decompose, even at −78 °C. In addition, lithiation‐deuteration studies reveal lithiation can take place competitively on both the triazole and the electron‐withdrawn aryl ring. Careful control of reaction conditions is therefore required to i) minimise decomposition pathways; and ii) facilitate regioselective functionalisation of the triazole.