8-methyl-2-(4-(trifluoromethyl)phenyl)imidazo[1,2-a]pyridine | 1449487-74-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 8-methyl-2-(4-(trifluoromethyl)phenyl)imidazo[1,2-a]pyridine
• 英文别名: 8-Methyl-2-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyridine
• CAS: 1449487-74-4
• 化学式: C₁₅H₁₁F₃N₂
• 分子量: 276.261
• InChiKey: VOOSUBRGGKWOFM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  17.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  8-methyl-2-(4-(trifluoromethyl)phenyl)imidazo[1,2-a]pyridine 在 4-(3-methylimidazolium)butanesulfonate 、 碘 作用下， 以 水 为溶剂， 反应 2.0h， 以59%的产率得到3-iodo-8-methyl-2-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyridine
  参考文献：
  名称：

  两性离子型熔融盐催化的水中碘化：碘咪唑并杂环的合成

  摘要：

  摘要 通过室温下水中的分子碘与sp 2 C–H键的官能化作用，开发了咪唑杂环杂环碘化的环境友好方案。该反应由基于咪唑的两性离子型熔融盐催化。已经合成了具有广泛功能的碘取代的咪唑并[1,2- a ]吡啶的文库。该方法学也适用于咪唑并[2，1- b ]噻唑和咪唑支架。 通过室温下水中的分子碘与sp 2 C–H键的官能化作用，开发了咪唑杂环杂环碘化的环境友好方案。该反应由基于咪唑的两性离子型熔融盐催化。已经合成了具有广泛功能的碘取代的咪唑并[1,2- a ]吡啶的文库。该方法学也适用于咪唑并[2，1- b ]噻唑和咪唑支架。

  DOI：

  10.1055/s-0035-1562492
• 作为产物：
  描述：

  2-氨基-3-甲基吡啶 、 2-溴-4'-(三氟甲基)苯乙酮 在 碳酸氢钠 作用下， 以 乙醇 为溶剂， 反应 8.0h， 以71%的产率得到8-methyl-2-(4-(trifluoromethyl)phenyl)imidazo[1,2-a]pyridine
  参考文献：
  名称：

  DMSO–POCl3: a reagent for methylthiolation of imidazo[1,2-a]pyridines and other imidazo-fused heterocycles

  摘要：

  A practical and metal free method for methylthiolation of imidazo[1,2-a]pyridines and other imidazo-fused heterocycles using DMSO-POCl3 complex is reported. The reactions are carried out at room temperature that give the corresponding methylthiolated products in good to excellent yield. Further, its application to indole has been demonstrated. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.07.017

文献信息

• Copper-catalyzed C–H ethoxycarbonyldifluoromethylation of imidazoheterocycles
  作者：Subhajit Mishra、Pallab Mondal、Monoranjan Ghosh、Susmita Mondal、Alakananda Hajra

  DOI：10.1039/c5ob02363g

  日期：——

  ethoxycarbonyl-difluoromethylation of imidazo[1,2-a]pyridines has been developed through sp2 C–H bond functionalization with BrCF2CO2Et under ambient air. A series of ethoxycarbonyldifluoromethylated imidazo[1,2-a]pyridines with broad functionalities have been synthesized. This methodology is also applicable to imidazo[2,1-b]thiazole and benzo[d]imidazo[2,1-b]thiazole.

  咪唑并[1,2- a ]吡啶在铜上的区域选择性铜催化的乙氧基羰基-二氟甲基化反应是通过在环境空气中用BrCF 2 CO 2 Et进行sp 2 C–H键官能化而开发的。合成了一系列具有广泛功能的乙氧基羰基二氟甲基化咪唑并[1,2- a ]吡啶。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。
• Electrochemical Oxidative C–H Thiocyanation or Selenocyanation of Imidazopyridines and Arenes
  作者：Ping Liu、Peipei Sun、Ting Cui、Xiaofeng Zhang、Jun Lin、Zitong Zhu

  DOI：10.1055/s-1299-3009

  日期：——

  electrochemical oxidative C–H thiocyanation or selenocyanation of imidazopyridines was achieved by using an undivided electrolytic cell. Transition-metal- and oxidant-free conditions are striking features of this protocol. A library of thiocyanated imidazopyridines with a broad range of functional groups were synthesized in high yields. This method was also applicable to the thiocyanation or selenocyanation of

  咪唑并吡啶的区域选择性电化学氧化C–H硫氰化或硒代氰化反应是通过使用未分割的电解池实现的。无过渡金属和无氧化剂的条件是该协议的显着特征。以高收率合成了具有广泛官能团的硫氰酸化咪唑并吡啶文库。该方法也适用于某些富电子芳烃的硫氰化或硒氰化。
• Cyanotriazole compounds
  申请人：OTSUKA PHARMACEUTICAL CO., LTD.

  公开号：US10626095B2

  公开（公告）日：2020-04-21

  This invention relates to a cyanotriazole compound represented by the formula (1): wherein each symbols are defined in the specification, or a salt thereof. The compound or a salt thereof stimulates the citric acid cycle activity and/or improves hyperglycemia with less side effects, and excellent safety, and therefore, it is useful for treating and/or preventing diseases or disorders on which citric acid cycle activation and/or improvement of hyperglycemia has a prophylactic and/or therapeutic effect, for example, diabetes, impaired glucose tolerance, insulin resistance, diabetic complications, obesity, dyslipidemia, hepatic steatosis, atherosclerosis and/or cardiovascular disease, as well as diseases or disorders that would benefit from stimulating energy expenditure.

  本发明涉及一种由式（1）表示的氰三唑化合物： 其中各符号在说明书中定义，或其盐。该化合物或其盐可刺激柠檬酸循环活性和/或改善高血糖，且副作用小、安全性高，因此可用于治疗和/或预防柠檬酸循环激活和/或改善高血糖具有预防和/或治疗作用的疾病或紊乱、例如，糖尿病、糖耐量受损、胰岛素抵抗、糖尿病并发症、肥胖症、血脂异常、肝脂肪变性、动脉粥样硬化和/或心血管疾病，以及可从刺激能量消耗中获益的疾病或紊乱。
• Visible-light-mediated C3-ethoxycarbonylmethylation of imidazo[1,2-a]pyridines and convenient access to Zolpidem
  作者：Yuanjiu Xiao、Lin Yu、Yongqi Yu、Ze Tan、Wei Deng

  DOI：10.1016/j.tetlet.2020.152606

  日期：2020.12
• Selective C-5 Oxidative Radical Silylation of Imidazopyridines Promoted by Lewis Acid
  作者：Yifan Li、Kaichen Shu、Ping Liu、Peipei Sun

  DOI：10.1021/acs.orglett.0c02131

  日期：2020.8.21

  An oxidative cross dehydrogenative coupling of imidazopyridines with silanes was developed using di-tert-butyl peroxide as the oxidant. The coordination effect of Lewis acid was the dominant factor controlling the regioselective addition of silyl radical to imidazopyridines, and the corresponding C-5 silylated imidazo[1,2-a]pyridines were obtained in moderate to high yields with a broad substrate scope.