三甘醇单苄醚在医药和农药领域有应用,具体用途需结合相关研究进一步明确。
医药; 农药
合成路线 1(1. 合成:55489-58-2)
产率:67%
合成条件:Stage #1: With sodium hydroxide In water for 0.17 h; Stage #2: at 100℃;
实验步骤:将三甘醇(30g,0.2mol)溶解在NaOH溶液(8g在8mL H 2 O中)中并搅拌10分钟。 然后加入苄基氯(7mL,0.062mol)并将反应混合物加热至100℃并搅拌过夜。 将粗反应物用饱和NaCl(500mL)稀释,用CH 2 Cl 2(2.x.400mL)洗涤,将有机层用MgSO 4干燥,并蒸发至干。 柱层析(硅胶,乙酸乙酯至乙酸乙酯/ MeOH,10:1),得到淡黄色油状物(9.87g,67%收率)。
参考文献:
- [1] European Journal of Organic Chemistry, 2008, # 17, p. 2900 - 2914 [2] Journal of the American Chemical Society, 2013, vol. 135, # 25, p. 9248 - 9251 [3] Synthetic Communications, 1986, vol. 16, # 1, p. 19 - 26 [4] Tetrahedron Letters, 2001, vol. 42, # 23, p. 3819 - 3822 [5] Patent: US2008/207505, 2008, A1. Location in patent: Page/Page column 31 [6] Journal of Chemical Research, Miniprint, 1984, # 9, p. 2672 - 2691 [7] Journal of Organic Chemistry, 1994, vol. 59, # 25, p. 7695 - 7700 [8] Analytical Chemistry, 1992, vol. 64, # 15, p. 1685 - 1690 [9] Journal of Pharmaceutical Sciences, 1975, vol. 64, # 4, p. 693 - 695 [10] Arzneimittel-Forschung, 1978, vol. 28, # 11, p. 2061 - 2063 [11] Synthetic Communications, 1990, vol. 20, # 6, p. 799 - 807 [12] Journal of the Chemical Society, Chemical Communications, 1990, # 13, p. 911 - 912 [13] Liebigs Annalen der Chemie, 1992, # 10, p. 1029 - 1032
合成路线 2(2. 合成:55489-58-2)
产率:92.9%
合成条件:With silver(l) oxide In dichloromethane for 2 h; Inert atmosphere
实验步骤:将Ag 2 O(6.9g,30mmol)加入到三甘醇(3.0g,20mmol)的无水CH 2 Cl 2溶液中。 然后在5分钟内滴加BnBr(2.6mL,22mmol),并将混合物搅拌2小时。 此后,将悬浮液通过硅藻土垫过滤,将其用CH 2 Cl 2彻底洗涤。 将合并的滤液减压浓缩,并将残余物通过柱色谱纯化,得到黄色油状物(4.46g,92.9%)。 1H NMR(300MHz,CDCl3):δ7.26-7.35(m,5H,Ph),4.56(s,2H,-CH2Ph),3.73-3.58(m,12H,-OCH2CH2O-),2.80(br,1H, -哦); 13 C NMR(75MHz,CDCl 3):δ138.0,128.2,127.6,127.5,73.1,72.4,70.5,70.4,70.2,69.2,61.5。
参考文献:
- [1] Tetrahedron, 2012, vol. 68, # 35, p. 7148 - 7154 [2] Journal of Organic Chemistry, 2004, vol. 69, # 3, p. 639 - 647 [3] Organic and Biomolecular Chemistry, 2009, vol. 7, # 6, p. 1064 - 1067 [4] Organic and Biomolecular Chemistry, 2009, vol. 7, # 18, p. 3652 - 3656 [5] Journal of Organic Chemistry, 2012, vol. 77, # 20, p. 8879 - 8887 [6] Chemical Communications, 2007, # 47, p. 5066 - 5068 [7] Chemistry - A European Journal, 2017, vol. 23, # 56, p. 13875 - 13878 [8] European Journal of Medicinal Chemistry, 2015, vol. 102, p. 153 - 166 [9] Carbohydrate Research, 1992, vol. 230, # 1, p. 117 - 149 [10] Journal of the American Chemical Society, 1994, vol. 116, # 12, p. 5057 - 5062 [11] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1994, # 5, p. 989 - 1002 [12] Analytical Chemistry, 1996, vol. 68, # 1, p. 208 - 215 [13] Canadian Journal of Chemistry, 2010, vol. 88, # 12, p. 1222 - 1232