1-methyl-2,5-dio-tolylimidazole | 920983-01-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-methyl-2,5-dio-tolylimidazole
• 英文别名: 1-methyl-2,5-di-o-tolyl-1H-imidazole；1-Methyl-2,5-bis(2-methylphenyl)-1H-imidazole；1-methyl-2,5-bis(2-methylphenyl)imidazole
• CAS: 920983-01-3
• 化学式: C₁₈H₁₈N₂
• 分子量: 262.354
• InChiKey: AFIGDTTWWOTQHR-UHFFFAOYSA-N

物化性质

• 沸点：
  440.2±53.0 °C(Predicted)
• 密度：
  1.05±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  N-甲基咪唑 、 2-溴甲苯 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23%的产率得到1-methyl-2,5-dio-tolylimidazole
  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

• Palladium-Catalyzed Intramolecular CH Arylation of Five-Membered <i>N</i>-Heterocycles
  作者：Atsunori Mori、Nobumichi Arai、Masabumi Takahashi、Makoto Mitani

  DOI：10.1055/s-2006-947326

  日期：2006.11

  Intramolecular CH arylation of imidazole derivatives is carried out in the presence of a palladium catalyst to form fused heteroaromatic compounds. The reaction of imidazole with 2-iodobenzyl bromide with NaH gives the cyclization precursor in an excellent yield. This then undergoes a palladium-catalyzed intramolecular CH arylation at 100 °C to form 5H-imidazo[5,1-a]isoindole in 78% yield.

  咪唑衍生物的分子内CH芳基化在钯催化剂的存在下进行，形成融合的杂芳香化合物。咪唑与2-碘苄溴化物在NaH的作用下反应，生成环化前体，收率极高。然后在100°C下进行钯催化的分子内CH芳基化反应，生成5H-咪唑[5,1-a]异吲哚，收率为78%。
• 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.
• Improved Synthesis of Symmetrical 2,5-Diarylimidazoles by One-Pot Palladium-Catalyzed Direct Arylation Tailored on the Electronic Features of the Aryl Halide
  作者：Marco Lessi、Gianmarco Panzetta、Giulia Marianetti、Fabio Bellina

  DOI：10.1055/s-0036-1589071

  日期：2017.10

  Two methods for the one-pot synthesis of 2,5-diarylimidazoles by palladium-catalyzed direct C–H arylation of 1-substituted imidazoles with aryl bromides have been devised. The first method, promoted by copper(I) iodide, is best suited for electron-poor aryl bromides, and also allows the 2,5-diarylation of thiazole and oxazole. The use of xylene instead of DMA is the key for the efficiency of the second

  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。