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.
• Synthesis, in vitro antifungal evaluation and docking studies of novel derivatives of imidazoles and benzimidazoles
  作者：Pegah Shojaei、Babak Mokhtari、Masoud Ghorbanpoor

  DOI：10.1007/s00044-019-02369-7

  日期：2019.9

  neoformans, A. niger, and M. gypseum with MIC 1.95 µg mL−1. The in silico molecular docking study was also done on the synthesized compounds and the results showed they have minimum binding energy and relatively good affinity toward cytochrome P450. According to the in vitro antifungal results and molecular docking studies, the compounds 6a–d can be selected as lead compounds for further pharmaceutical investigations

  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。