2-(2-methyl-1H-imidazol-1-yl)-1-phenylethan-1-ol | 22159-32-6

• 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-(2-methyl-1H-imidazol-1-yl)-1-phenylethan-1-ol
• 英文别名: 2-(2-methyl-1-imidazolyl)-1-phenylethanol；2-(2-methyl-imidazol-1-yl)-1-phenyl-ethanol；Imidazole-1-ethanol, 2-methyl-alpha-phenyl-；2-(2-methylimidazol-1-yl)-1-phenylethanol
• CAS: 22159-32-6
• 化学式: C₁₂H₁₄N₂O
• 分子量: 202.256
• InChiKey: WXCRAXNWCZKFDZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 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

• 作为反应物：
  描述：

  2-(2-methyl-1H-imidazol-1-yl)-1-phenylethan-1-ol 以51%的产率得到
  参考文献：
  名称：

  COOPER G.; IRWIN W. J., J. CHEM. SOC. PERKIN TRANS., PART. I. , 1976, NO 5, 545-549

  摘要：

  DOI：
• 作为产物：
  描述：

  氧化苯乙烯 、 2-甲基咪唑 在 四正丁基溴化膦 作用下， 以 neat (no solvent) 为溶剂， 生成 2-(2-methyl-1H-imidazol-1-yl)-1-phenylethan-1-ol
  参考文献：
  名称：

  咪唑和苯并咪唑新衍生物的合成，体外抗真菌评价和对接研究

  摘要：

  设计了一系列咪唑和苯并咪唑衍生物，并使用容易获得的起始原料，通过方便有效的两步合成路线，以高收率制备。通过IR，1 H-NMR，13 C-NMR光谱和MS光谱表征合成的化合物及其中间体的结构。评估了目标化合物对白色念珠菌，新型隐球菌，黑曲霉和石膏微孢子菌的体外抗真菌活性。结果表明，这些唑类衍生物中的一些对所用菌株，特别是新孢梭菌和黑曲霉，表现出良好至优异的抗真菌活性。。例如，化合物6b 1- [2-苯基-2-（3-苯基-丙氧基）-乙基] -1H-咪唑在MIC 1.95的情况下对新孢梭菌，黑曲霉和石膏霉非常有效。微克mL -1。还对合成的化合物进行了计算机分子对接研究，结果表明它们具有最小的结合能，并且对细胞色素P450的亲和力相对较好。根据体外抗真菌结果和分子对接研究，可以选择化合物6a – d作为进一步的药物研究的先导化合物。

  DOI：

  10.1007/s00044-019-02369-7

文献信息

• Fluoroboric acid adsorbed on silica gel catalyzed regioselective ring opening of epoxides with nitrogen heterocycles
  作者：B.P. Bandgar、Abasaheb V. Patil

  DOI：10.1016/j.tetlet.2006.10.118

  日期：2007.1

  Aryl epoxides can be opened in a regioselective and efficient manner with nitrogen heterocycles such as indoles, pyrroles and imidazoles in the presence of a catalytic amount of HBF4–SiO2 under mild conditions to afford the corresponding C-alkylated derivatives in good yields and with a high regioselectivity.

  在温和的条件下，在催化量的HBF 4 -SiO 2存在下，可以与氮杂环（如吲哚，吡咯和咪唑）以区域选择性和高效的方式打开芳基环氧化物，从而以高收率和高收率得到相应的C-烷基化衍生物高区域选择性。
• Ultrasound-assisted regioselective ring opening of epoxides with nitrogen heterocycles using pyrrolidonium and imidazolium-based acidic ionic liquids
  作者：Masoumeh Zakeri、Mohamed Mahmoud Nasef、Ebrahim Abouzari-Lotf、Hoda Haghi

  DOI：10.1007/s11164-015-2015-4

  日期：2015.12

  Imidazolium and N-methyl-2-pyrrolidonium ionic liquids under ultrasound irradiation were developed as a green and expeditious approach for C--alkylation and N-alkylation of the nitrogen heterocycles including indoles and imidazoles with aliphatic and aromatic epoxides. Ionic liquids were used with a dual role of catalyst and solvent. The highest yield (85 %) was obtained with N-methyl-2-pyrrolidonium dihydrogen phosphate [H-NMP]H2PO4 as a pyrrolidonium ionic liquid under ultrasound at 50 kHz, with a reaction time of 60 min and reaction temperature of 60 °C. The combination of ionic liquids and ultrasonic irradiation was found to be an effective, green and eco-friendly method for alkylation of indoles and imidazoles.

  在超声辐射下，开发了咪唑鎓和N-甲基-2-吡咯烷鎓离子液体作为一种绿色快速的方法，用于氮杂环的C-烷基化和N-烷基化，包括吲哚和咪唑与脂肪族和芳香族环氧化物。离子液体在催化剂和溶剂中具有双重作用。在超声频率50 kHz、反应时间60分钟和反应温度60°C的条件下，使用N-甲基-2-吡咯烷鎓二氢磷酸盐[H-NMP]H2PO4作为吡咯烷鎓离子液体获得了最高产率（85%）。离子液体与超声辐射的结合被认为是一种有效、绿色且环保的方法，用于吲哚和咪唑的烷基化。
• 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.
• High-Pressure Organic Chemistry. 19. High-Pressure-Promoted, Silica Gel-Catalyzed Reaction of Epoxides with Nitrogen Heterocycles¹^,
  作者：Hiyoshizo Kotsuki、Katsunori Hayashida、Tomoyasu Shimanouchi、Hitoshi Nishizawa

  DOI：10.1021/jo951106t

  日期：1996.1.1

  The reaction of epoxides with nitrogen heterocycles such as indoles, pyrroles, imidazoles, and pyrazoles was studied under both high-pressure and silica gel-catalyzed conditions. Whereas it has been reported that the treatment of indole with styrene aside at in kbar and 42 degrees C for 24 h gave 2-(3-indolyl)-2-phenylethanol in 56% yield, the same compound was obtained in 88% yield when the reaction was conducted on silica gel at rt for 1 week. Similarly, efficient reaction of epoxides with pyrroles, imidazoles, and pyrazoles was achieved. In terms of stereochemical features, the epoxide ring opening reaction of (R)-(+)-styrene oxide with indole was found to proceed stereoselectively in an S(N)2 fashion at the benzyl carbon, in either ease.