3-methyl-1-(phenylethynyl)-1H-pyrazole | 1304789-32-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-methyl-1-(phenylethynyl)-1H-pyrazole
• 英文别名: 3-Methyl-1-(2-phenylethynyl)pyrazole；3-methyl-1-(2-phenylethynyl)pyrazole
• CAS: 1304789-32-9
• 化学式: C₁₂H₁₀N₂
• 分子量: 182.225
• InChiKey: OQKCWQWCNWHHRT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 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：

  3-甲基吡唑 、 2,2-dibromostyrene 在 溴代(1,10-菲咯啉)(三苯基膦)铜(I) 、 caesium carbonate 作用下， 以 二甲基亚砜 为溶剂， 反应 3.0h， 以68%的产率得到3-methyl-1-(phenylethynyl)-1H-pyrazole
  参考文献：
  名称：

  Copper-catalyzed coupling of imidazoles and pyrazoles with 1,1-dibromo-1-alkenes: a distinct approach for direct N-alkynylation of heteroarenes

  摘要：

  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.

  DOI：

  10.1016/j.tetlet.2011.09.117

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.