2-methyl-1-(2-phenylethynyl)-1H-imidazole | 1046136-16-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-methyl-1-(2-phenylethynyl)-1H-imidazole
• 英文别名: 2-methyl-1-(phenylethynyl)-1H-imidazole；2-Methyl-1-(2-phenylethynyl)imidazole
• CAS: 1046136-16-6
• 化学式: C₁₂H₁₀N₂
• 分子量: 182.225
• InChiKey: XRHBHONTJIAACV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 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：

  2-甲基咪唑 、 2,2-dibromostyrene 在 copper(l) iodide 、 四甲基乙二胺 、 caesium carbonate 作用下， 以 1,4-二氧六环 为溶剂， 反应 24.0h， 以67%的产率得到2-methyl-1-(2-phenylethynyl)-1H-imidazole
  参考文献：
  名称：

  一种简单高效的铜催化合成N-炔基咪唑

  摘要：

  通过铜催化的交叉偶联反应，开发了一种由1,1-二溴-1-烯烃合成N-炔基杂芳烃的简单有效的方法。在二恶烷中使用咪唑和苯并咪唑底物，以TMEDA为配体可获得通常较高的收率和官能团耐受性。 N-炔基咪唑-1,1-二溴-1-烯烃-铜-交叉偶联反应-烷基化

  DOI：

  10.1055/s-0031-1290340

文献信息

• Copper(II) Oxide Catalyzed Ligand-Free Coupling Reaction of Heteroarenes with Bromoalkynes¹
  作者：Biswanath Das、Gandolla Reddy、Penagaluri Balasubramanyam、N. Salvanna

  DOI：10.1055/s-0030-1258403

  日期：2011.3

  The coupling reaction of imidazoles and pyrazoles with bromoacetylenes has efficiently been carried out under ligand-free conditions in the presence of copper(II) oxide as the catalyst using potassium hydroxide in 1,4-dioxane at 80 ˚C. The method is a simpler access to N-alk-1-ynyl- and/or N-(2-bromovinyl)-substituted heteroarenes. coupling reaction - ligand-free conditions - copper(II) oxide - N-alkynylheteroarene

  咪唑和吡唑与溴乙炔的偶联反应已在无配体条件下，在氧化铜（II）催化剂存在下，在80°C下于1,4-二恶烷中使用氢氧化钾的条件下有效进行。该方法更容易获得N-烷-1-炔基和/或N-（2-溴乙烯基）取代的杂芳烃。 偶联反应-无配体条件-氧化铜（II）-N-炔基杂芳烃-N-（2-溴乙烯基）杂芳烃 “新型合成方法研究”系列中的第217部分。
• Copper-catalyzed coupling of imidazoles and pyrazoles with 1,1-dibromo-1-alkenes: a distinct approach for direct N-alkynylation of heteroarenes
  作者：Biswanath Das、N. Salvanna、Gandolla Chinna Reddy、Penagaluri Balasubramanyam

  DOI：10.1016/j.tetlet.2011.09.117

  日期：2011.11

  The direct N-alkynylation of heteroarenes, imidazoles, and pyrazoles with 1,1-dibromo-1-alkene has been carried out for the first time using [Cu(Phen)PPh3Br] (as a catalyst) and Cs2CO3 in DMSO at 80 degrees C. The products are formed in good to high yields (66-85%) within 3 h. No side products could be detected. (C) 2011 Elsevier Ltd. All rights reserved.
• Coupling Reactions of Bromoalkynes with Imidazoles Mediated by Copper Salts: Synthesis of Novel <i>N</i>-Alkynylimidazoles
  作者：Christophe Laroche、Jing Li、Matthew W. Freyer、Sean M. Kerwin

  DOI：10.1021/jo801118q

  日期：2008.8.1

  A cross-coupling reaction of imidazoles with bromoalkynes in the presence of a catalytic amount of CuI is reported. This protocol allows an access to novel N-(1-alkynyl)imidazoles in moderate to good yields.
• Cu-Catalyzed N<i>-</i>Alkynylation of Imidazoles, Benzimidazoles, Indazoles, and Pyrazoles Using PEG as Solvent Medium
  作者：Glenn A. Burley、David L. Davies、Gerry A. Griffith、Michael Lee、Kuldip Singh

  DOI：10.1021/jo902466f

  日期：2010.2.5

  A facile and efficient Cu(I)-catalyzed cross-coupling method is reported for the preparation of N-alkynyl or N-bromoalkenyl heteroarenes from bromoalkynes. Generally superior yields and functional group tolerance were obtained with microwave (MW) irradiation using imidazole, benzimidazole, pyrazole, and indazole substrates and poly(ethylene glycol) 400 (PEG400) as an additive. We speculate that PEG400 acts as both a Cu(I)-stabilizing ligand as well as a phase transfer solvent.
• Lithiation and functionalization of 1-alkynylimidazoles at the 2-position
  作者：Christophe Laroche、Sean M. Kerwin

  DOI：10.1016/j.tetlet.2009.06.133

  日期：2009.9

  Functionalization reactions of 1-alkynylimidazoles involving the formation of their 2-lithio derivatives followed by addition of various electrophiles are presented. This allows access to previously unreported 1,2-dialkynylimidazoles via 1-alkynyl-2-iodoimidazoles. The use of an aldehyde or sulfonimine electrophiles allows the direct formation of bicyclic ring systems. (C) 2009 Elsevier Ltd. All rights reserved.