3-(4-(苄氧基)苯基)丙酸甲酯主要用于医药领域,具体用途在提供的文献中未详细说明,但根据其化学结构推测可能与药物合成相关。
医药
合成路线 1(1. 合成:24807-40-7)
产率:88%
合成条件:With potassium carbonate In acetonitrile for 1 h; Reflux
实验步骤:3- [4-(苄氧基)苯基]丙酸甲酯; 将BnBr(4.39g,25.64mmol)加入到K 2 CO 3(3.55g,25.64mmol)和3-(4-羟基苯基)丙酸甲酯(1.54g,8.55mmol)在CH 3 CN(40mL)中的悬浮液中。 将反应混合物升温至回流,并使其反应1小时。 将其倒入H 2 O(120mL)中,用HCl(10%水溶液)吸收至pH = 2,并用EtOAc(2×100mL)萃取。 将有机层用Na 2 SO 4(无水)干燥,过滤并浓缩。 将粗残余物在SiO 2(0→5%EtOAc /己烷)上进行快速色谱分离,得到2.01g 3- [4-(苄氧基)苯基]丙酸甲酯(白色固体,产率:88%)。1 H NMR(CDCl 3, 250MHz)δppm:7.51-7.29(m,5H),7.14(d,J = 8.8Hz,2H),6.92(d,J = 8.8Hz,2H),5.05(s,2H),3.69(s, 3H),2.92(t,J = 7.6Hz,2H),2.62(t,J = 7.6Hz,2H)。
参考文献:
- [1] Patent: US2002/65246, 2002, A1 [2] Patent: US6414179, 2002, B1 [3] Patent: WO2010/70076, 2010, A1. Location in patent: Page/Page column 104 [4] Patent: EP2952517, 2015, A1. Location in patent: Paragraph 0217 [5] Bulletin of the Polish Academy of Sciences, Chemistry, 1986, vol. 34, # 3-4, p. 115 - 122 [6] Journal of Medicinal Chemistry, 2001, vol. 44, # 21, p. 3351 - 3354 [7] Tetrahedron, 1973, vol. 29, p. 1405 - 1411 [8] Patent: WO2004/74270, 2004, A2. Location in patent: Page 316-317 [9] Patent: US2005/176701, 2005, A1. Location in patent: Page/Page column 153 [10] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 6, p. 1939 - 1944 [11] Patent: WO2003/95441, 2003, A1. Location in patent: Page/Page column 15-16 [12] Patent: EP1849465, 2007, A1. Location in patent: Page/Page column 81 [13] ACS Medicinal Chemistry Letters, 2010, vol. 1, # 7, p. 345 - 349 [14] RSC Advances, 2016, vol. 6, # 46, p. 40238 - 40249 [15] Patent: WO2008/130514, 2008, A1. Location in patent: Page/Page column 104
合成路线 2(2. 合成:24807-40-7)
产率:59%
合成条件:With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 0℃; for 2 h;
实验步骤:参考实施例1 4-(苯基甲氧基)苯丙酸甲酯向冰冷的4-羟基苯丙酸甲酯(0.70g,3.9mmol),苯甲醇(0.48mL,4.7mmol)和三苯基膦(1.2g,4.7mmol)的四氢呋喃溶液( 向其中滴加5mL)偶氮二甲酸二乙酯(0.73mL,4.7mmol),并将混合物在冰冷却下搅拌2小时。 向反应溶液中加入水,并将反应混合物用乙酸乙酯萃取。 萃取液用水洗涤,然后减压浓缩。 用硅胶柱色谱(己烷/乙酸乙酯= 17:3)纯化残余物,得到标题化合物(0.62g,产率59%),为粉末。 1H NMR(CDCl3)δ2.59(2H,t,J = 7.5Hz),2.89(2H,t,J = 7.5Hz),3.66(3H,s),5.04(2H,s),6.90(2H,d, J = 8.6Hz),7.11(2H,d,J = 8.6Hz),7.29-7.44(5H,m)。
参考文献:
- [1] Patent: EP1688138, 2006, A1. Location in patent: Page/Page column 76 [2] Patent: EP1559422, 2005, A1. Location in patent: Page/Page column 70