3,4,5-三(苄氧基)苯甲酸甲酯在医药和农药领域有广泛应用,具体用途需结合相关研究和专利进一步明确。
医药; 农药
合成路线 1(1. 合成:70424-94-1)
产率:100%
合成条件:With potassium carbonate In N,N-dimethyl-formamide at 120℃; for 7 h;
实验步骤:将碳酸钾(63.31g,400mmol)和苄基溴(59.47mL,500mmol)加入到3,4,5-三羟基苯甲酸甲酯(化合物60)(18.41g,100mmol)的DMF(70mL)溶液中。)。 将该反应混合物在120℃下搅拌7小时,然后倒入水中。 用乙酸乙酯萃取混合物。 将有机层用Na 2 SO 4干燥并减压浓缩。 以定量收率得到标题化合物61(3,4,5-三苄氧基苯甲酸甲酯)(47.19g)。 化合物61的NMR光谱示于表29中。表29化合物61400MHz的NMR光谱1H NMR(CDCl3)δ7.45-7.24(17H,m,Ar-H),5.14(4H,s,ArCH2O),5.11( 2H,s,ArCH 2 O),3.89(3H,s,CO 2 CH 3)。
参考文献:
- [1] Patent: EP1870403, 2007, A1. Location in patent: Page/Page column 95 [2] Patent: US2004/110790, 2004, A1. Location in patent: Page 14 [3] Bioscience, Biotechnology and Biochemistry, 2003, vol. 67, # 12, p. 2584 - 2590 [4] Patent: US7288273, 2007, B1. Location in patent: Page/Page column 38 [5] Synthetic Communications, 2002, vol. 32, # 20, p. 3149 - 3158 [6] Patent: WO2017/176948, 2017, A1. Location in patent: Page/Page column 117; 118; 121 [7] Journal of Medicinal Chemistry, 1996, vol. 39, # 1, p. 86 - 95 [8] Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences, 2009, vol. 64, # 4, p. 464 - 466 [9] Synthetic Communications, 2006, vol. 36, # 5, p. 587 - 597 [10] Dalton Transactions, 2011, vol. 40, # 45, p. 12067 - 12074 [11] Chinese Journal of Chemistry, 2010, vol. 28, # 2, p. 303 - 308 [12] Tetrahedron Letters, 2016, vol. 57, # 24, p. 2652 - 2654 [13] Bioscience, Biotechnology and Biochemistry, 1999, vol. 63, # 8, p. 1453 - 1462 [14] Tetrahedron Letters, 2016, vol. 57, # 49, p. 5469 - 5474 [15] Journal of the American Chemical Society, 2013, vol. 135, # 41, p. 15609 - 15616 [16] Monatshefte fur Chemie, 2018, vol. 149, # 7, p. 1293 - 1300 [17] Journal of the American Chemical Society, 2016, vol. 138, # 33, p. 10508 - 10515 [18] Journal of the American Chemical Society, 1998, vol. 120, # 12, p. 2908 - 2918 [19] Organic and Biomolecular Chemistry, 2014, vol. 12, # 1, p. 73 - 85 [20] Phytochemistry, 1999, vol. 52, # 5, p. 759 - 767 [21] Organic Letters, 2008, vol. 10, # 12, p. 2593 - 2596 [22] Organic and Biomolecular Chemistry, 2012, vol. 10, # 13, p. 2590 - 2593 [23] Australian Journal of Chemistry, 1991, vol. 44, # 9, p. 1307 - 1333 [24] Chemical and Pharmaceutical Bulletin, 2003, vol. 51, # 9, p. 1085 - 1088 [25] Journal of the American Chemical Society, 2004, vol. 126, # 32, p. 9882 - 9883 [26] Organic Letters, 2001, vol. 3, # 6, p. 843 - 845 [27] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 7, p. 2191 - 2194 [28] Journal of Agricultural and Food Chemistry, 2010, vol. 58, # 20, p. 11081 - 11089 [29] Patent: WO2011/119866, 2011, A1. Location in patent: Page/Page column 27-28 [30] Journal of Medicinal Chemistry, 2014, vol. 57, # 9, p. 3724 - 3736 [31] Chemistry - A European Journal, 2015, vol. 21, # 43, p. 15235 - 15245 [32] Heterocycles, 2014, vol. 8, # 2, p. 1371 - 1396