3-benzyl-6-methyl-2-phenylimidazo[1,2-a]pyridine | 1245815-61-5

• 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-benzyl-6-methyl-2-phenylimidazo[1,2-a]pyridine
• 英文别名: 3-benzyl-6-methyl-2-phenyl-1H-imidazo[1,2-a]pyridine；3-Benzyl-6-methyl-2-phenylimidazo[1,2-a]pyridine
• CAS: 1245815-61-5
• 化学式: C₂₁H₁₈N₂
• 分子量: 298.387
• InChiKey: SWBILOJGMRIAQL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  17.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  苯乙炔 在 正丁基锂 、 copper(l) chloride 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 正己烷 、 甲苯 为溶剂， 反应 26.0h， 生成 3-benzyl-6-methyl-2-phenylimidazo[1,2-a]pyridine
  参考文献：
  名称：

  芳基丙炔醇与 2-氨基吡啶的串联胺化/环异构化作为制备咪唑 [1,2-a] 吡啶的便捷途径

  摘要：

  通过芳基炔丙醇与 2-氨基吡啶的直接胺化及其随后的分子内环异构化，探索了一种导致咪唑并 [1,2-a] 吡啶的新串联路线。已开发出 ZnCl2 / CuCl 系统来促进这种转化，从而以中等至良好的产率生成各种咪唑并 [1,2-a] 吡啶。

  DOI：

  10.1002/ejoc.201101053

文献信息

• Synthesis of imidazo[1,2a]pyridines via three-component reaction of 2-aminopyridines, aldehydes and alkynes
  作者：Ping Liu、Li-song Fang、Xinsheng Lei、Guo-qiang Lin

  DOI：10.1016/j.tetlet.2010.05.139

  日期：2010.9

  A novel three-component reaction towards the synthesis of imidazo[1,2a]pyridines was independently developed based on 2-aminopyridines, aldehydes and alkynes, and thereby imidazo[1,2a]pyridines were obtained in acceptable yields by the CuSO4/TsOH catalyzed three-component reaction.

  向咪唑并[1,2的合成一种新型三组分反应一]吡啶是独立的基础上研制2-氨基吡啶，醛和炔烃，从而咪唑并[1,2一个在由硫酸铜可接受的产率得到〕吡啶/ TsOH催化三组分反应。
• Nano Fe3O4 supported biimidazole Cu(i) complex as a retrievable catalyst for the synthesis of imidazo[1,2-a]pyridines in aqueous medium
  作者：Mahmood Tajbakhsh、Maryam Farhang、Rahman Hosseinzadeh、Yaghoub Sarrafi

  DOI：10.1039/c4ra03333g

  日期：——

  A novel magnetically recoverable nano-catalyst based on a biimidazole Cu(I) complex has been synthesized by covalent grafting of biimidazole on chloride-functionalized silica@magnetite nanoparticles, followed by metalation with CuI. The synthesized catalyst was characterized by various techniques such as CHN, NMR, FT-IR, TG/DTG, SEM, TEM, EDS, XRD, AAS, ICP-OES and VSM which revealed the superparamagnetic nature of the particles. The amount of Cu in the catalyst was measured to be 1.2 mmol g−1 by ICP-OES and AAS. From electron microscopy (SEM and TEM) studies it can be inferred that the particles are mostly spherical in shape and have an average size of 20 nm. Elemental and thermo gravimetric analysis (CHN and TG) results indicate the loading amount of functionalized organic groups on the magnetic material was 1.4 mmol g−1. The prepared nanocatalyst was shown to have excellent and green catalytic activity in the synthesis of imidazo[1,2-a]pyridines in aqueous media. The catalyst can be easily recovered by applying an external magnetic field and reused for atleast 10 times without deterioration in catalytic activity.

  一种新型的可磁性回收纳米催化剂是通过将双咪唑Cu(I)络合物以共价方式接枝到氯功能化的二氧化硅@磁铁矿纳米颗粒上，并随后用CuI进行金属化而合成的。通过多种技术对合成的催化剂进行了表征，包括CHN、NMR、FT-IR、TG/DTG、SEM、TEM、EDS、XRD、AAS、ICP-OES和VSM，这些结果揭示了颗粒的超顺磁性。通过ICP-OES和AAS测得催化剂中铜的含量为1.2 mmol g−1。根据电子显微镜（SEM和TEM）研究可以推断，这些颗粒大多呈球形，平均尺寸为20 nm。元素分析和热重分析（CHN和TG）结果表明，功能化有机基团在磁性材料上的负载量为1.4 mmol g−1。所制备的纳米催化剂在水相介质中合成咪唑[1,2-a]吡啶方面表现出优异的绿色催化活性。该催化剂可以通过施加外部磁场轻松回收，并可重复使用至少10次而不降低催化活性。
• Semistabilized Diazatrienyl Anions from Pyridine Imines and Acetylenes: An Access to (<i>Z</i>)-Stilbene/Imidazopyridine Ensembles, Benzyl Imidazopyridines, and Beyond
  作者：Ivan A. Bidusenko、Elena Yu. Schmidt、Igor A. Ushakov、Alexander V. Vashchenko、Nadezhda I. Protsuk、Vladimir B. Orel、Nadezhda M. Vitkovskaya、Boris A. Trofimov

  DOI：10.1021/acs.joc.2c01372

  日期：2022.9.16

  Semistabilized diazatrienyl anions are generated by the reaction of 2-pyridylarylimines with arylacetylenes in superbase systems MOtBu (M = Li, Na, K)/DMSO at ambient temperature for 15 min. The initial intermediate N-centered propargyl-1,3-diaza-1,3,5-trienyl anions undergo intermolecular cyclization to benzyl imidazopyridine anions (formally [3 + 2] cycloaddition), further intercepting a second molecule

  通过 2-吡啶基芳基亚胺与芳基乙炔在超碱体系 MO t Bu (M = Li, Na, K)/DMSO 在环境温度下反应 15 分钟，产生半稳定的二氮杂三烯基阴离子。初始中间体N中心的炔丙基-1,3-二氮杂-1,3,5-三烯基阴离子经历分子间环化为苄基咪唑并吡啶阴离子（形式为 [3 + 2] 环加成），进一步拦截起始吡啶亚胺的第二个分子或介质的质子提供 ( Z )-芪/咪唑并吡啶合奏和苄基咪唑并吡啶。所有中间阴离子的电荷分布及其合成演化与量子化学分析（B2PLYPD/6-311+G**//B3LYP/6-31+G*）一致。
• Tandem Amination/Cycloisomerization of Aryl Propargylic Alcohols with 2-Aminopyridines as an Expedient Route to Imidazo[1,2-a]pyridines
  作者：Ping Liu、Chun-Lin Deng、Xinsheng Lei、Guo-qiang Lin

  DOI：10.1002/ejoc.201101053

  日期：2011.12

  A new tandem route leading to imidazo[1,2-a]pyridines has been explored through the direct amination of aryl propargylic alcohols with 2-aminopyridines and their subsequent intramolecular cycloisomerization. A ZnCl2/CuCl system has been developed to promote this transformation, which resulted in various imidazo[1,2-a]pyridines in moderate to good yields.

  通过芳基炔丙醇与 2-氨基吡啶的直接胺化及其随后的分子内环异构化，探索了一种导致咪唑并 [1,2-a] 吡啶的新串联路线。已开发出 ZnCl2 / CuCl 系统来促进这种转化，从而以中等至良好的产率生成各种咪唑并 [1,2-a] 吡啶。