该化合物主要用于医药和农药领域,作为关键中间体或活性成分。
医药; 农药
合成路线1
- 步骤: 将2,4,5-三氟苯基乙酸(25g,0.132mol)、Meldrum酸(21g,0.145mol)和DMAP(1.29g,0.0011mol)加入1000mL三颈烧瓶,室温下加入乙腈(75mL);保持温度<40℃,加入N,N-二异丙基乙胺(49.2mL,0.283mol);1-2小时内滴加新戊酰氯(17.8mL,0.145mol),控制温度<40℃;滴毕后45-50℃搅拌2-3小时,冷却至0℃;1小时内滴加1N HCl(300mL),结晶析出产物;过滤,20%MeCN/水洗涤,干燥得36.5g产物。
- 条件: 乙腈溶剂,反应温度分阶段控制(室温→45-50℃→0℃),HCl浓度1N,洗涤液20%MeCN/水。
- 收率: 88%。
- 结构确认: 1H-NMR(400MHz, CDCl3)δ15.50(s,1H),7.14(m,1H),6.96(m,1H),4.45(s,2H),1.76(s,6H);13C-NMR(100MHz, CDCl3)δ192.76,170.66,160.42,156.47(ddd,JCF=245.7,9.6,2.4Hz),149.79(ddd,JCF=251.4,14.5,12.0Hz),146.90(ddd,JCF=244.9,12.0,3.2Hz),119.40(dd,JCF=19.3,5.6Hz),117.41(ddd,JCF=18.5,5.6,4.0Hz),105.80(dd,JCF=28.1,20.9Hz),105.63,91.99,34.59,27.06ppm。
- 参考文献: [1] Bioorganic and Medicinal Chemistry Letters, 2007, 17(9), 2622-2628;[2] Journal of the American Chemical Society, 2004, 126(40), 13002-13009;[3] Journal of the American Chemical Society, 2009, 131(25), 8798-8804;[4] Patent: WO2004/83212, 2004, A1;[5] Patent: CN107501112, 2017, A;[6] Patent: WO2004/83212, 2004, A1;[7] Patent: CN105566138, 2016, A;[8] Patent: US2012/108598, 2012, A1;[9] Patent: WO2009/85990, 2009, A2;[10] Patent: WO2010/131025, 2010, A1;[11] Patent: WO2004/85378, 2004, A1;[12] Patent: WO2005/97733, 2005, A1;[13] Patent: WO2006/33848, 2006, A1;[14] Patent: WO2007/35198, 2007, A2;[15] Patent: WO2007/50485, 2007, A2;[16] Patent: WO2005/20920, 2005, A2;[17] Patent: WO2009/84024, 2009, A2;[18] Patent: WO2005/72530, 2005, A1;[19] Patent: WO2006/65826, 2006, A2;[20] Patent: US2010/317856, 2010, A1;[21] Patent: WO2012/42534, 2012, A2;[22] Patent: CN102363599, 2016, B;[23] Patent: CN103923087, 2016, B;[24] Patent: WO2006/119260, 2006, A2;[25] Patent: WO2005/20920, 2005, A2。