3-phenyl-2-(trifluoromethyl)imidazo[1, 2-a]pyridine | 1188436-33-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-phenyl-2-(trifluoromethyl)imidazo[1, 2-a]pyridine
• 英文别名: 3-Phenyl-2-(trifluoromethyl)imidazo[1,2-a]pyridine；3-phenyl-2-(trifluoromethyl)imidazo[1,2-a]pyridine
• CAS: 1188436-33-0
• 化学式: C₁₄H₉F₃N₂
• 分子量: 262.234
• InChiKey: UDLLOUUHHZLZFT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  19
• 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：

  2-氨基吡啶 在 copper(l) iodide 、 1,10-菲罗啉 、 potassium tert-butylate 、 potassium carbonate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 44.0h， 生成 3-phenyl-2-(trifluoromethyl)imidazo[1, 2-a]pyridine
  参考文献：
  名称：

  咪唑并[1,2- a ]吡啶在C-3上通过铜（I）催化的C–H键官能化与芳基碘化物，溴化物和三氟甲磺酸酯直接芳构化

  摘要：

  开发了一种方便的方法，用于铜（I）催化的取代的咪唑并[1,2- a ]吡啶的芳基化。该方法适用于各种芳基亲电试剂，包括溴化物，碘化物和三氟甲磺酸酯。它代表了通过Cu（I）催化C-3取代的咪唑并[1,2- a ]吡啶的C-3芳构化的第一个通用方法，该反应构建了各种功能化的咪唑并[1,2- a ]吡啶的核π系统。

  DOI：

  10.1021/ol300232a

文献信息

• Pd-catalyzed oxidative cross-coupling of imidazo[1,2-a]pyridine with arenes
  作者：Shaohua Wang、Wenjie Liu、Jinghe Cen、Jinqiang Liao、Jianping Huang、Haiying Zhan

  DOI：10.1016/j.tetlet.2014.01.069

  日期：2014.2

  A facile method for direct Pd(OAc)2-catalyzed oxidative cross-coupling of unactivated imidazo[1,2-a]pyridine with simple arenes has been developed. The reaction shows good reaction efficiency, high regioselectivity, and good functional-group compatibility. This approach provides a useful protocol for the preparation of imidazo[1,2-a]pyridine–arene structure of interest in biological and pharmaceutical

  已开发了一种简便的方法，用于未活化的咪唑并[1,2- a ]吡啶与简单的芳烃的直接Pd（OAc）2催化的氧化交叉偶联。该反应显示出良好的反应效率，高的区域选择性和良好的官能团相容性。该方法为生物和药物材料中感兴趣的咪唑并[1,2 - a ]吡啶-芳烃结构的制备提供了有用的方案。
• Conversion of Pyridine to Imidazo[1,2-<i>a</i>]pyridines by Copper-Catalyzed Aerobic Dehydrogenative Cyclization with Oxime Esters
  作者：Huawen Huang、Xiaochen Ji、Xiaodong Tang、Min Zhang、Xianwei Li、Huanfeng Jiang

  DOI：10.1021/ol403105p

  日期：2013.12.20

  A rapid and environmentally friendly conversion of pyridine to imidazo[1,2-a]pyridines has been developed via copper-catalyzed aerobic dehydrogenative cyclization with ketone oxime esters.

  通过铜与酮肟酯的需氧脱氢环化反应，已开发了吡啶向咪唑并[1,2- a ]吡啶的快速环保转化。
• Synthetic Approach to Alkoxy-β-(trifluoromethyl)styrenes and Their Application in the Synthesis of New Trifluoromethylated Heterocycles
  作者：Valentine Nenajdenko、Günter Haufe、Vasiliy Muzalevskiy、Aleksey Shastin、Elizabeth Balenkova

  DOI：10.1055/s-0029-1216697

  日期：2009.7

  A new convenient stereoselective pathway to alkoxy-β-(trifluoromethyl)styrenes is described. Reactions of β-chloro- and β-bromo-β-(trifluoromethyl)styrenes with sodium methoxide and potassium tert-butoxide led to methoxy- and tert-butoxy-β-(trifluoromethyl)styrenes in good to excellent yields. Bromination of tert-butoxy-β-(trifluoromethyl)styrenes proceeded with formation of aryl(bromo)methyl trifluoromethyl

  描述了一种新的方便的烷氧基-β-（三氟甲基）苯乙烯的立体选择途径。β-氯-和β-溴-β-（三氟甲基）苯乙烯与甲醇钠和叔丁醇钾的反应生成甲氧基-和叔丁氧基-β-（三氟甲基）苯乙烯，收率好至优异。叔丁氧基-β-（三氟甲基）苯乙烯的溴化反应形成芳基（溴）甲基三氟甲基酮。发现后一种化合物是用于合成带有三氟甲基的不同杂环化合物的有用起始原料。以这种方式，以中等至高产率获得了咪唑并吡啶，咪唑并嘧啶，咪唑并苯并咪唑，咪唑并噻唑，噻唑和氨基噻唑的三氟甲基化衍生物。 烯烃-炔烃-醚-氟-杂环-亲核取代
• Highly regioselective palladium-catalyzed direct cross-coupling of imidazo[1,2-a]pyridines with arylboronic acids
  作者：Limin Zhao、Haiying Zhan、Jinqiang Liao、Jianping Huang、Qinlin Chen、Huifang Qiu、Hua Cao

  DOI：10.1016/j.catcom.2014.06.028

  日期：2014.11

  A highly regioselective method for the palladium-catalyzed direct cross-coupling of imidazo[1,2-a]pyridines with arylboronic acids has been developed by using O-2 as oxidant. This process can be applied to a wide range of imidazo[1,2-a]pyridines and arylboronic acids with excellent C-3-regioselectivity. It provides a new way for developing C-C bond-forming processes of multisubstituted imidazo[1,2-a]pyridines, which are common structural motifs in natural products and pharmaceuticals. (C) 2014 Elsevier B.V. All rights reserved.
• Highly regioselective C H bond functionalization of imidazo[1,2-a]pyridines with aryl halides catalyzed by Ru-arene complex
  作者：Hai Yang、Liping Yang、Yuan Li、Fan Zhang、Huajie Liu、Bing Yi

  DOI：10.1016/j.catcom.2012.04.032

  日期：2012.9

  An effective Ru-catalyzed coupling reaction of imidazo[1,2-a]pyridines and aryl halides is reported for the synthesis of polysubstituted imidazo[1,2-a]pyridines through C-H bond cleavages. The current study presents a convenient strategy to synthesize polysubstituted imidazo[1,2-a]pyridine, a common structural motif in natural products and pharmaceuticals. Desired products in considerable yields can be obtained in the presences of [RuCl2(P-cymene)](2) and Cs2CO3 in DMF at 120 degrees C after 15 h. (C) 2012 Elsevier B.V. All rights reserved.