1,1'-((1-methyl-1H-imidazole-2,5-diyl)bis(4,1-phenylene))bis(ethan-1-one) | 1333128-03-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,1'-((1-methyl-1H-imidazole-2,5-diyl)bis(4,1-phenylene))bis(ethan-1-one)
• 英文别名: 1-[4-[2-(4-acetylphenyl)-3-methylimidazol-4-yl]phenyl-]ethanone
• CAS: 1333128-03-2
• 化学式: C₂₀H₁₈N₂O₂
• 分子量: 318.375
• InChiKey: DUSNILUCMICQDG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.16
• 重原子数：
  24.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  51.96
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  N-甲基咪唑 、 4-溴苯乙酮 在 cesium acetate 、 palladium diacetate 、 copper(l) iodide 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 48.0h， 以63%的产率得到1,1'-((1-methyl-1H-imidazole-2,5-diyl)bis(4,1-phenylene))bis(ethan-1-one)
  参考文献：
  名称：

  根据芳基卤化物的电子特征，通过一锅钯催化的直接芳基化反应改进了对称的2,5-二芳基咪唑的合成

  摘要：

  已经设计了两种通过钯催化1-取代的咪唑与芳基溴的直接C–H芳基化反应一锅合成2,5-二芳基咪唑的方法。由碘化铜（I）促进的第一种方法最适合于电子贫乏的芳基溴化物，并且还可以使噻唑和恶唑进行2,5-二芳基化。使用二甲苯代替DMA是提高第二种方法效率的关键，对于富电子的芳基溴化物，该方法可获得最佳结果。

  DOI：

  10.1055/s-0036-1589071

文献信息

• Direct C5-Arylation Reaction between Imidazoles and Aryl Chlorides Catalyzed by Palladium Complexes with Phosphines and N-Heterocyclic Carbenes
  作者：P. Vijaya Kumar、Wu-Shien Lin、Jiun-Shian Shen、Debkumar Nandi、Hon Man Lee

  DOI：10.1021/om200490k

  日期：2011.10.10

  Palladium(II) acetate complexes bearing phosphines and carbene ligands, Pd(L)(PR3)(OAc)2 (1a, R = Ph; 1b, R = Cy; L = 1,3-dibenzylimidazol-2-ylidene), were prepared by salt metathesis reactions of their chloro complexes with AgOAc in good yields. The electron-rich 1b was efficient in catalyzing C-5 direct arylation of imidazoles with aryl halides. Most significantly, the catalytic system allows a range

  带有膦和卡宾配体的钯钯（II）配合物Pd（L）（PR 3）（OAc）2（1a，R = Ph; 1b，R = Cy; L = 1,3-二苄基咪唑-2-亚烷基），通过氯络合物与AgOAc的盐复分解反应以高收率制备了这些化合物。富电子1b在催化咪唑与芳基卤化物的C-5直接芳基化方面非常有效。最重要的是，催化系统允许使用多种芳基氯作为底物。微波辐射可有效促进反应，仅2小时即可获得良好的收率。结合经典的C–C键形成反应方法，成功地从1,4-二氯苯和1-溴-4-氯苯中获得了具有联芳基和苯乙烯基亚基的新型咪唑衍生物。
• One pot Pd(OAc)2-catalysed 2,5-diarylation of imidazoles derivatives
  作者：Abdelilah Takfaoui、Liqin Zhao、Rachid Touzani、Jean-François Soulé、Pierre H. Dixneuf、Henri Doucet

  DOI：10.1016/j.tet.2014.09.012

  日期：2014.11

  The regioselective 2- or 5-arylation of imidazole derivatives with aryl halides using palladium catalysts has been described in recent years; whereas the arylation at both C2 and C5 carbons of imidazoles in high yields has not been performed. We found conditions allowing the access to these 2,5-diarylimidazoles via a one pot reaction. The choice of the base was found to be crucial to obtain these products in high yields. Using CsOAc as the base, DMA as the solvent and only 2 mol % of the phosphine-free Pd(OAc)(2) the catalyst, the target 2,5-diarylated imidazoles were obtained in moderate to good yields with a wide variety of aryl bromides. Substituents such as fluoro, trifluoromethyl, formyl, acetyl, propionyl, ester, nitro or nitrile on the aryl bromide were tolerated. Sterically congested aryl bromides or heteroaryl bromides can also be employed. Surprisingly the nature of the substituent at position 1 on the imidazole derivative exhibits a huge influence on the reaction. (C) 2014 Elsevier Ltd. All rights reserved.