3,5-二苄氧基苯甲醛主要用于化学合成,也可用作研究用化合物。
化学合成; 研究用化合物
合成路线 1(14615-72-6)
- 步骤: 向3,5-双(苄氧基)苄醇(9.9g,31.0mmol)的CH₂Cl₂(140mL)溶液中加入DMSO(22mL,0.31mol)和二异丙基乙胺(26.92mL,0.154mol);将混合物冷却至0℃并加入SO₃·吡啶(14.76g,92.73mmol);在0℃下搅拌1小时,用饱和Na₂S₂O₃水溶液(310mL)淬灭;用乙酸乙酯(3×200mL)萃取,合并有机层,用MgSO₄干燥;蒸发溶剂,通过硅胶柱色谱法(CH₂Cl₂)纯化,得到产物。
- 条件: With sulfur trioxide pyridine complex; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine In dichloromethane at 0℃; for 1 h
- 收率: 93%
- 参考文献: [1] Journal of Organic Chemistry, 1998, vol. 63, #25, p.9367-9374; [2] Journal of Medicinal Chemistry, 1993, vol.36, #20, p.2950-2955; [3] Chemistry - A European Journal, 2009, vol.15, #10, p.2278-2288; [4] ChemCatChem, 2017, vol.9, #20, p.3880-3887; [5] ACS Catalysis, 2018, vol.8, #4, p.3030-3034; [6] Journal of Organic Chemistry, 1997, vol.62, #4, p.908-915; [7] Bulletin of the Chemical Society of Japan, 1983, vol.56, #6, p.1889-1890; [8] Beilstein Journal of Organic Chemistry, 2013, vol.9, p.2320-2327; [9] Journal of Medicinal Chemistry, 1985, vol.28, #1, p.12-17; [10] Synthetic Communications, 2002, vol.32, #20, p.3149-3158; [11] Journal of Medicinal Chemistry, 1997, vol.40, #8, p.1186-1194; [12] Helvetica Chimica Acta, 1980, vol.63, #8, p.2508-2514; [13] Chemistry - A European Journal, 2002, vol.8, #2, p.408-432; [14] Russian Chemical Bulletin, 2004, vol.53, #4, p.830-833; [15] Journal of the American Chemical Society, 1997, vol.119, #2, p.283-291; [16] Journal of Heterocyclic Chemistry, 1973, vol.10, p.649-654; [17] Tetrahedron Letters, 1988, vol.29, #19, p.2347-2348; [18] Synthetic Communications, 1998, vol.28, #6, p.1097-1102; [19] Journal of the American Chemical Society, 2004, vol.126, #32, p.9882-9883; [20] Journal of the American Chemical Society, 2006, vol.128, #10, p.3324-3334; [21] Journal of Organic Chemistry, 1983, vol.48, #12, p.1941-1944; [22] Synlett, 2008, #12, p.1801-1804
合成路线 2(14615-72-6)
- 步骤: 向搅拌的酚醛(2.00mmol)的无水丙酮(10mL)溶液中加入K₂CO₃(3.00mmol,1.5当量);在氮气氛中冷却至0℃,缓慢加入苄基溴(2.4mmol,1.2当量);将混合物温度升至40℃,搅拌12小时;反应完成后冷却至室温,通过硅藻土垫过滤并真空浓缩;通过柱色谱法(EtOAc/己烷=1/3)纯化粗化合物,得到纯芳香醛。
- 条件: With potassium carbonate In acetone at 0-40℃; for 12 h; Inert atmosphere
- 收率: 90%
- 参考文献: [1] Bioorganic and Medicinal Chemistry Letters, 2016, vol.26, #22, p.5438-5443; [2] Patent: KR2018/16809, 2018, A. Location in patent: Paragraph 0104; 0111-0113; 0116; 0124; 0125; [3] European Journal of Medicinal Chemistry, 2016, vol.108, p.730-740; [4] Tetrahedron, 1994, vol.50, #38, p.11097-11112; [5] Journal of Enzyme Inhibition and Medicinal Chemistry, 2011, vol.26, #5, p.643-648