2-(2-Methylimidazol-1-yl)-2-phenylethanol | 99500-92-2

• 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-(2-Methylimidazol-1-yl)-2-phenylethanol
• CAS: 99500-92-2
• 化学式: C₁₂H₁₄N₂O
• 分子量: 202.256
• InChiKey: PAOYIHXSOCIYOP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  38
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  氧化苯乙烯 、 2-甲基咪唑 在 nanocrystalline zirconium based zeolite 作用下， 以 neat (no solvent) 为溶剂， 反应 0.75h， 生成 2-(2-Methylimidazol-1-yl)-2-phenylethanol 、 2-(2-methyl-1H-imidazol-1-yl)-1-phenylethan-1-ol
  参考文献：
  名称：

  Highly efficient and green chemical synthesis of imidazolyl alcohols and N-imidazolyl functionalized β-amino compounds using nanocrystalline ZSM-5 catalysts

  摘要：

  A solvent free protocol is developed for the synthesis of imidazolyl alcohols and N-imidazolyl functionalized beta-amino compounds. Imidazolyl alcohols were synthesized by the ring opening of epoxides with imidazoles and N-imidazolyl functionalized beta-amino compounds were synthesized by the hydroamdination reaction of imidazoles and activated olefins. These reactions were catalyzed by a variety of crystalline heterogeneous catalysts such as Al/Zr substituted nanocrystalline ZSM-5 (M-Nano-ZSM-5), conventional M-ZSM-5 (where M=Zr, Al), and Zr substituted amorphous mesoporous catalysts (Zr-SBA15 and Zr-KIT-6). Among these catalysts, nanocrystalline Zr-Nano-ZSM-5 exhibited the highest activity and regioselectivity. Structure activity relationship is explained based on the catalytic activity, acidity measurements, reactivity of reactants (imidazoles/epoxides/methyl acrylate), competitive adsorption, nature, and type of catalysts. Zr-Nano-ZSM-5 exhibited exceptionally high catalytic activity compared to the catalysts reported in the literature for the synthesis of imidazolyl alcohols and other imidazole derivatives. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.apcata.2014.03.006

文献信息

• Substituierte Imidazole
  申请人：CIBA-GEIGY AG

  公开号：EP0149976A2

  公开（公告）日：1985-07-31

  Substituierte Imidazole der allgemeinen Formel oder deren Salze, worin Ph unsubstituiertes oder durch Niederalkyl oder Niederalkoxy substituiertes Phenyl bedeutet und R1 und R2 jeweils Niederalkyl bedeuten, Verfahren zu ihrer Herstellung, ihre Verwendung sowie pharmazeutische Präparate. Die Verbindungen der Formel I weisen beispielseise antidepressive Eigenschaften auf.

  通式如下的取代咪唑 或其盐类，其中 Ph 是未被取代或被低级烷基或低级烷氧基取代的苯基，R1 和 R2 分别是低级烷基，它们的制备工艺、用途和药物制剂。 例如，式 I 的化合物具有抗抑郁特性。
• Highly efficient and green chemical synthesis of imidazolyl alcohols and N-imidazolyl functionalized β-amino compounds using nanocrystalline ZSM-5 catalysts
  作者：Rajkumar Kore、Biswarup Satpati、Rajendra Srivastava

  DOI：10.1016/j.apcata.2014.03.006

  日期：2014.5

  A solvent free protocol is developed for the synthesis of imidazolyl alcohols and N-imidazolyl functionalized beta-amino compounds. Imidazolyl alcohols were synthesized by the ring opening of epoxides with imidazoles and N-imidazolyl functionalized beta-amino compounds were synthesized by the hydroamdination reaction of imidazoles and activated olefins. These reactions were catalyzed by a variety of crystalline heterogeneous catalysts such as Al/Zr substituted nanocrystalline ZSM-5 (M-Nano-ZSM-5), conventional M-ZSM-5 (where M=Zr, Al), and Zr substituted amorphous mesoporous catalysts (Zr-SBA15 and Zr-KIT-6). Among these catalysts, nanocrystalline Zr-Nano-ZSM-5 exhibited the highest activity and regioselectivity. Structure activity relationship is explained based on the catalytic activity, acidity measurements, reactivity of reactants (imidazoles/epoxides/methyl acrylate), competitive adsorption, nature, and type of catalysts. Zr-Nano-ZSM-5 exhibited exceptionally high catalytic activity compared to the catalysts reported in the literature for the synthesis of imidazolyl alcohols and other imidazole derivatives. (C) 2014 Elsevier B.V. All rights reserved.