(2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl)(phenyl)methanone | 1374639-83-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl)(phenyl)methanone
• 英文别名: [2-(4-Chlorophenyl)imidazo[1,2-a]pyridin-3-yl]-phenylmethanone；[2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl]-phenylmethanone
• CAS: 1374639-83-4
• 化学式: C₂₀H₁₃ClN₂O
• 分子量: 332.789
• InChiKey: PSAJEJFNVDMABF-UHFFFAOYSA-N

物化性质

• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  34.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-(4-乙基苯基)乙酸 在 氯化亚砜 、 potassium carbonate 作用下， 以 乙腈 为溶剂， 生成 (2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl)(phenyl)methanone
  参考文献：
  名称：

  Toward versatile methods leading to highly functionalized imidazo[1,2-a]pyridines

  摘要：

  A convenient and general method of preparation of polyfunctionalized imidazo[1,2-a]pyridines is reported. This methodology involves activation of secondary amides leading to the formation of the corresponding amidines 9. Different activating reagents have been evaluated and the efficiency of PCl5 was illustrated with alkyl functionalized groups. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.02.117

文献信息

• Copper(II)-Catalyzed Aerobic Oxidative Coupling between Chalcone and 2-Aminopyridine<i>via</i>CH Amination: An Expedient Synthesis of 3-Aroylimidazo[1,2-<i>a</i>]pyridines
  作者：Kamarul Monir、Avik Kumar Bagdi、Subhajit Mishra、Adinath Majee、Alakananda Hajra

  DOI：10.1002/adsc.201300900

  日期：2014.3.24

  A simple and efficient protocol has been developed for the synthesis of 3‐aroylimidazopyridines via copper(II) acetate‐catalyzed aerobic oxidative amination. A library of 3‐aroylimidazopyridines was synthesized from readily accessible chalcones and 2‐aminopyridines with high yields and regioselectivity. The reaction proceeds through a tandem Michael addition followed by an intramolecular oxidative

  已开发出一种简单有效的方案，用于通过乙酸铜（II）催化的需氧氧化胺化合成3-芳基咪唑并吡啶。由易于获得的查耳酮和2-氨基吡啶合成了一个3-aroylimidazopyridines文库，具有很高的产率和区域选择性。反应通过串联迈克尔加成反应进行，随后进行分子内氧化胺化。这种方法在克级反应中的成功应用表明其具有大量合成的潜力。
• Superparamagnetic nanoparticle-catalyzed coupling of 2-amino pyridines/pyrimidines with <i>trans</i>-chalcones
  作者：Oanh T. K. Nguyen、Pha T. Ha、Ha V. Dang、Yen H. Vo、Tung T. Nguyen、Nhan T. H. Le、Nam T. S. Phan

  DOI：10.1039/c9ra00097f

  日期：——

  An aerobic coupling of 2-aminopyrimidines or 2-aminopyridines with trans-chalcones to afford aroylimidazo[1,2-a]pyrimidines and aroylimidazo[1,2-a]pyridines is reported. Reactions proceed in the presence of CuFe2O4 superparamagnetic nanoparticle catalyst, two equivalents of iodine, oxygen oxidant, and 1,4-dioxane solvent. The catalyst is superior to many common copper or iron complexes. Copper ferrite

  报道了 2-氨基嘧啶或 2-氨基吡啶与反式查耳酮的需氧偶联，得到芳酰基咪唑并[1,2 - a ]嘧啶和芳酰基咪唑并[1,2- a ]吡啶。反应在 CuFe 2 O 4超顺磁性纳米颗粒催化剂、两当量碘、氧氧化剂和 1,4-二恶烷溶剂的存在下进行。该催化剂优于许多常见的铜或铁络合物。铁氧体铜可以很容易地通过磁倾析分离并重复使用多达 5 次而不会造成重大的活性损失。这里描述的方法标志着使用简单的非均相催化剂合成稠合杂环的罕见例子。据我们所知，芳酰咪唑[1,2- a]嘧啶和芳酰咪唑并[1,2- a ]吡啶以前没有使用该协议合成。
• Copper supported on H⁺-modified manganese oxide octahedral molecular sieves (Cu/H-OMS-2) as a heterogeneous biomimetic catalyst for the synthesis of imidazo[1,2-a]-N-heterocycles
  作者：Xu Meng、Jinqi Zhang、Baohua Chen、Zhenqiang Jing、Peiqing Zhao

  DOI：10.1039/c5cy01433f

  日期：——

  A combination of Cu and H-OMS-2 is employed to synthesize heterocycles through multistep oxidation under a low-energy pathway.

  使用Cu和H-OMS-2的组合在低能途径下进行多步氧化，用于合成杂环化合物。
• One-pot, three component tandem reaction of 2-aminopyridines, acetophenones and aldehydes: synthesis of 3-aroylimidazo[1,2-a]pyridines
  作者：Pinku Kaswan、Kasiviswanadharaju Pericherla、Hitesh Kumar Saini、Anil Kumar

  DOI：10.1039/c4ra13056a

  日期：——

  A facile synthesis of 3-aroylimidazo[1,2-a]pyridine derivatives has been achieved through the one-pot, three-component tandem reaction of acetophenones, arylaldehydes and 2-aminopyridines in the presence of a catalytic amount of copper(II) chloride and air as the sole oxidant. The developed one-pot method is atom-economical and utilizes readily available precursors to offer highly functionalized N-fused

  3- aroylimidazo [1,2的简便合成一个]吡啶衍生物已经通过苯乙酮，芳醛和2-氨基吡啶在铜催化量的存在的一锅煮，三组分串联反应实现（II）氯化物和空气为唯一氧化剂。发达的一锅法是原子经济的，它利用现成的前体以中等到良好的产率（26-82％）提供高度官能化的N稠合咪唑。预期的串联工艺将通过交叉的羟醛缩合，迈克尔加成，铜催化的氧化环化和随后的芳构化来进行。
• Toward versatile methods leading to highly functionalized imidazo[1,2-a]pyridines
  作者：Alexandra Basilio-Lopes、Thiago Mendonça de Aquino、Alexandre Mongeot、Jean-Jacques Bourguignon、Martine Schmitt

  DOI：10.1016/j.tetlet.2012.02.117

  日期：2012.5

  A convenient and general method of preparation of polyfunctionalized imidazo[1,2-a]pyridines is reported. This methodology involves activation of secondary amides leading to the formation of the corresponding amidines 9. Different activating reagents have been evaluated and the efficiency of PCl5 was illustrated with alkyl functionalized groups. (C) 2012 Elsevier Ltd. All rights reserved.