6-bromo-2-phenyl-3-(trifluoromethyl)imidazo[1,2-a]pyridine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 6-bromo-2-phenyl-3-(trifluoromethyl)imidazo[1,2-a]pyridine
• 英文别名: 6-Bromo-2-phenyl-3-(trifluoromethyl)imidazo[1,2-a]pyridine
• 化学式: C₁₄H₈BrF₃N₂
• 分子量: 341.13
• InChiKey: ACCIUFRPLWRLPP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  17.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-(三氟甲基)-1,2-苯碘酰-3(1H)-酮 、 6-溴-2-苯基咪唑并[1,2-a]吡啶 在 potassium phosphate 、 [Cu₄I₄(PPh₃)₄] 作用下， 以 1,4-二氧六环 为溶剂， 反应 6.0h， 以60%的产率得到6-bromo-2-phenyl-3-(trifluoromethyl)imidazo[1,2-a]pyridine
  参考文献：
  名称：

  Copper(I)-catalyzed direct C-H trifluoromethylation of imidazoheterocycles with Togni’s reagent

  摘要：

  A mild and efficient trifluoromethylation of imidazopyridines with Togni's reagent in the presence of inexpensive base has been realized at room temperature. This methodology has several advantages: (1) using efficient copper(I) as catalyst and inexpensive K3PO4 as base, (2) no additional oxidants required for this reaction. (3) good functional group tolerance. An array of trifluoromethylated imidazopyridines with broad functionalities were obtained in acceptable yields. (C) 2019 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2019.01.026

文献信息

• Regioselective Oxidative Trifluoromethylation of Imidazoheterocycles via C(sp²)–H Bond Functionalization
  作者：Kamarul Monir、Avik Kumar Bagdi、Monoranjan Ghosh、Alakananda Hajra

  DOI：10.1021/jo502928e

  日期：2015.2.6

  been carried out at room temperature through the functionalization of the sp2 C–H bond employing Langlois reagent under ambient air. A library of 3-(trifluoromethyl)imidazo[1,2-a]pyridines with broad functionalities have been synthesized regioselectively. This methodology is also applicable to imidazo[2,1-b]thiazole and benzo[d]imidazo[2,1-b]thiazole.

  咪唑并吡啶的氧化三氟甲基化反应已在室温下通过使用Langlois试剂对sp 2 C–H键进行官能化来进行。已经选择性地合成了具有广泛功能的3-（三氟甲基）咪唑并[1,2- a ]吡啶的文库。该方法也适用于咪唑并[2,1- b ]噻唑和苯并[ d ]咪唑并[2,1- b ]噻唑。
• Transition‐Metal‐Free Direct Trifluoromethylation and Perfluoroalkylation of Imidazopyridines under Mild Conditions
  作者：Shuaijun Han、Xianying Gao、Qingsong Wu、Jingya Li、Dapeng Zou、Yangjie Wu、Yusheng Wu

  DOI：10.1002/adsc.201801541

  日期：2019.4

  The first transition‐metal‐free method for direct C−H trifluoromethylation of imidazo[1,2‐a]pyridine derivatives with readily available Ruppert‐Prakash reagent TMSCF3 under mild conditions was described. Moreover, this method could be applied to direct C−H perfluoroalkylation of imidazopyridines, affording a series of novel perfluoroalkylated products in moderate to good yields. Notable advantages

  描述了在温和条件下用现成的Ruppert-Prakash试剂TMSCF 3直接进行咪唑并[1,2-a]吡啶衍生物的CHH三氟甲基化的第一种无过渡金属的方法。而且，该方法可用于咪唑并吡啶的直接CH全氟烷基化，以中等到良好的产率提供一系列新颖的全氟烷基化产物。该协议的显着优势包括易于操作，高效和广泛的底物范围。
• Visible-Light-Promoted Metal-Free C-H Trifluoromethylation of Imidazopyridines
  作者：Xia Mi、Yuanfang Kong、Huaixia Yang、Jingyu Zhang、Chao Pi、Xiuling Cui

  DOI：10.1002/ejoc.201901860

  日期：2020.2.28

  An efficient, mild and photo redox‐based protocol for the C–H trifluoromethylation of imidazo[1,2‐a]pyridines has been developed using acridinium as photo redox catalyst and the easy‐handling CF3SO2Na as CF3 source. A series of desired products were afforded in satisfied yields under transition‐metal‐free condition, which displays potential for further application in synthetic research.

  已经开发了一种高效，温和且基于光氧化还原的协议，该方法使用cri啶作为光氧化还原催化剂，并使用易于处理的CF 3 SO 2 Na作为CF 3来源，开发了咪唑并[1,2- a ]吡啶的CHH三氟甲基化反应。在无过渡金属的条件下，以令人满意的产率提供了一系列所需的产品，这显示了在合成研究中进一步应用的潜力。
• 一种三氟甲基咪唑稠环类化合物及其制备方 法
  申请人：河南中医药大学

  公开号：CN110590774B

  公开（公告）日：2020-09-08

  本发明涉及一种三氟甲基咪唑稠环类化合物及其制备方法，属于咪唑稠环类化合物的合成领域。该三氟甲基咪唑稠环类化合物的结构通式如式Ⅰ所示，其中A为五元杂环或六元杂环，B为苯基、吡啶基或噻吩基；R1为氢、烷基、烷氧基、卤素、酯基或三氟甲基；R2为氢、烷基、烷氧基、卤素、三氟甲基或砜基；所述烷基、烷氧基、酯基、砜基中的碳原子数为1‑6。该化合物以咪唑环和五元杂环或六元杂环进行稠合为母体，在其C3位实现三氟甲基化，三氟甲基基团具有强吸电子诱导效应，含有稳定的碳氟键，将其引入到母体结构中，可显著地改变分子的酸性、偶极矩、亲脂性及代谢稳定性，具有潜在的良好生物活性。
• Copper(I)-catalyzed direct C-H trifluoromethylation of imidazoheterocycles with Togni’s reagent
  作者：Ruonan Wang、Jingcai Wang、Qingxuan Tang、Xin Zhao、Junfeng Wang、Yuting Leng、Yangjie Wu、Junbiao Chang、Yusheng Wu、Zhaoda Zhang、Shiwei Wang

  DOI：10.1016/j.tetlet.2019.01.026

  日期：2019.2

  A mild and efficient trifluoromethylation of imidazopyridines with Togni's reagent in the presence of inexpensive base has been realized at room temperature. This methodology has several advantages: (1) using efficient copper(I) as catalyst and inexpensive K3PO4 as base, (2) no additional oxidants required for this reaction. (3) good functional group tolerance. An array of trifluoromethylated imidazopyridines with broad functionalities were obtained in acceptable yields. (C) 2019 Elsevier Ltd. All rights reserved.