3-(2-methoxyphenyl)imidazo[1,5-a]pyridine | 160037-68-3

• 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-(2-methoxyphenyl)imidazo[1,5-a]pyridine
• 英文别名: 3-(2-methoxylphenyl)imidazo[1,5-a]pyridine
• CAS: 160037-68-3
• 化学式: C₁₄H₁₂N₂O
• 分子量: 224.262
• InChiKey: LUOKERDKAWLLCU-UHFFFAOYSA-N

物化性质

• 熔点：
  119-121 °C
• 密度：
  1.15±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  26.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(2-methoxyphenyl)imidazo[1,5-a]pyridine 在 N-碘代丁二酰亚胺 、 1,1'-bis(diisopropylphosphino)ferrocene 、 palladium diacetate 、 caesium carbonate 作用下， 以 1,4-二氧六环 、 乙腈 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  用于铃木-宫浦交叉偶联反应的 3-芳基-1-膦基咪唑并[1,5-a]吡啶配体的合成。

  摘要：

  3-芳基-1-膦基咪唑并[1,5-a]吡啶配体以2-氨基甲基吡啶为初始底物，通过两条互补路线合成。第一个合成途径经历了 2-氨基甲基吡啶与取代的苯甲酰氯的偶联，然后进行环化、碘化和钯催化的交叉偶联次膦化反应序列，得到我们的磷配体。在第二条路线中，2-氨基甲基吡啶用芳基醛环化，然后进行碘化和钯催化的交叉偶联次膦化反应，得到我们的磷配体。在钯催化的空间位阻联芳基和杂联芳基 Suzuki-Miyaura 交叉偶联反应中评估了 3-芳基-1-膦基咪唑并[1,5-a]吡啶配体。

  DOI：

  10.1039/d1ra05417a
• 作为产物：
  描述：

  N-(2-methoxybenzyl)picolinamide 在 三氯氧磷 作用下， 以11%的产率得到3-(2-methoxyphenyl)imidazo[1,5-a]pyridine
  参考文献：
  名称：

  Microwave-assisted organic synthesis of 3-substituted-imidazo[1,5-a]pyridines

  摘要：

  3-Substituted-imidazo[1,5-a]pyridines were conveniently synthesized in two steps from commercially available picolinic esters under microwave irradiation conditions. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.10.137

文献信息

• Direct Sequential C3 and C1 Arylation Reaction of Imidazo[1,5-<i>a</i>]pyridine Catalyzed by a 1,10-Phenanthroline–Palladium Complex
  作者：Eiji Yamaguchi、Fumitoshi Shibahara、Toshiaki Murai

  DOI：10.1246/cl.2011.939

  日期：2011.9.5

  The direct sequential arylation reaction at the C3 and C1 positions of imidazo[1,5-a]pyridines with a variety of aryl iodides catalyzed by [Pd(phen)2](PF6)2 is described. The reaction of unsubstitu...

  描述了在 [Pd(phen)2](PF6)2 催化下，咪唑并 [1,5-a] 吡啶与各种芳基碘化物在 C3 和 C1 位置的直接连续芳基化反应。未取代的反应...
• [EN] DIKETOPYRROLOPYRROLES HAVING THREE DIFFERENT SUBSTITUENTS AS EMITTERS OF YELLOW, ORANGE AND RED LIGHT, AND THE METHOD OF THEIR PREPARATION<br/>[FR] DICÉTOPYRROLOPYRROLES AYANT TROIS SUBSTITUANTS DIFFÉRENTS EN TANT QU'ÉMETTEURS DE LUMIÈRE JAUNE, ORANGE ET ROUGE, ET LEUR PROCÉDÉ DE PRÉPARATION
  申请人：INST CHEMIII ORGANICZNEJ PAN

  公开号：WO2020242329A1

  公开（公告）日：2020-12-03

  New derivatives of diketopyrrolopyrroles (well-known organic pigments) having three different substituents and a new method of obtaining them have been disclosed. These dyes can be used as highly fluorescent substances with advantageous properties. These compounds can be obtained by the method according to the invention in no more than a four-step synthesis from simple, readily available and cheap substrates.

  已经披露了具有三种不同取代基的新二酮吡咯吡咯（著名的有机颜料）衍生物以及获得它们的新方法。这些染料可以用作具有优越性质的高荧光物质。这些化合物可以通过根据本发明的方法从简单、易得和廉价的底物中不超过四步合成获得。
• A new synthetic route for synthesis of <scp>3‐substituted</scp> imidazo[1,5‐ <i>a</i> ]pyridines
  作者：Jugal Bori、Vadivelu Manivannan

  DOI：10.1002/jhet.4449

  日期：2022.6

  A new convenient route for the synthesis of 3-substituted-imidazo[1,5-a]pyridines has been described as well as the scope and limitations of the method are evaluated. By reacting 2-picolylamine and different aldehydes in presence of selenium dioxide as the oxidant, a series of 3-substituted imidazo[1,5-a]pyridines was isolated in good yields. Different kinds of aldehydes such as aliphatic, aromatic

  描述了合成 3-取代的咪唑并[1,5- a ]吡啶的一种新的便捷途径，并评估了该方法的范围和局限性。通过在二氧化硒作为氧化剂存在下使2-吡啶甲胺和不同的醛反应，以良好的收率分离出一系列3-取代的咪唑并[1,5- a ]吡啶。已经使用了不同种类的醛，例如脂肪族、芳香族、杂环以及带有一些取代基的芳香环。
• Photoinduced Intramolecular Proton Transfer and Charge Redistribution in Imidazopyridines
  作者：Abderrazzak Douhal、Francisco Amat-Guerri、A. Ulises Acuna

  DOI：10.1021/j100001a014

  日期：1995.1

  The ground-state conformation and fluorescence properties of two closely related dyes 2-(2'-hydroxyphenyl)imidazo[1,2-a]pyridine (1,2-HPIP) and 3-(2'-hydroxyphenyl)imidazo[1,5-a]pyridi (1,5-HPIP) have been studied in various solvents at room temperature to determine the origin of the large red-shifted emission spectra. The two compounds have a ground-state planar conformation stabilized by an intramolecular ii bond (MB) between the imino and phenol groups. On electronic excitation in cyclohexane solution a weak fluorescence is observed in the two dyes, with large Stokes shifts (1,2-HPIP: lambda(max) = 588 nm, Delta v = 11 000 cm(-1) 1,5-HPIP: lambda(max) 440 nm, Delta v = 9000 cm(-1)). For the first dye it is proposed that the emission takes place from a zwitterion produced by a proton-transfer reaction in the singlet manifold. A quinonoid, neutral phototautomer is excluded on the basis of the electronic structure of the molecule. In the case of 1,5-HPIP, the IHB is broken on electronic excitation and neither a proton nor H atom transfer occurs due to the reversal of the proton affinity of the imino group. The anomalous fluorescence is assigned to significant changes in the geometry of the emitting state following excitation.