1700-37-4 3-苄氧基苯甲醛
词条详情加载中…
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安全说明
运输信息：常温运输。危险描述：非危险化学品，WGK Germany:3，危险等级为IRRITANT，海关编码29124990，存储类别11 - 可燃固体。
用途与制备
化学合成，医药中间体。
医药中间体
产率：99% 合成条件：With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 14 h; 实验步骤：将3-羟基苯甲醛（3g，24.6mmol）和碳酸钾（10.2g，73.8mmol）悬浮在N，N-二甲基甲酰胺（60mL）中。将苄基溴（3.21mL，27.1mmol）加入到该悬浮液中，并在室温下搅拌14小时。将该混合物分配到乙酸乙酯和水中。分离有机层，用水洗涤，用无水硫酸镁干燥，过滤。减压浓缩滤液，用硅胶柱色谱（庚烷：乙酸乙酯= 4：1-1：1）纯化残余物，得到标题化合物（5.16g，99％）。1H-NMR谱（CDCl3）δ（ppm）：5.13（2H，s），7.24-7.25（1H，m），7.35-7.49（8H，m），9.98（1H，s）。 参考文献：[1] Journal of the American Chemical Society, 1994, vol. 116, # 18, p. 8402 - 8403 [2] Journal of Medicinal Chemistry, 2015, vol. 58, # 7, p. 3188 - 3208 [3] Patent: US2007/105904, 2007, A1. Location in patent: Page/Page column 112 [4] Molecules, 2010, vol. 15, # 11, p. 7971 - 7984 [5] Journal of the American Chemical Society, 2001, vol. 123, # 22, p. 5382 - 5383 [6] Patent: US2014/23603, 2014, A1. Location in patent: Paragraph 0284; 0285 [7] Patent: KR101677122, 2016, B1. Location in patent: Paragraph 0443-0444 [8] Journal of the American Chemical Society, 2010, vol. 132, # 40, p. 14021 - 14023 [9] Patent: WO2017/100757, 2017, A1. Location in patent: Page/Page column 0043 [10] Journal of Medicinal Chemistry, 1991, vol. 34, # 7, p. 2176 - 2186 [11] Patent: WO2017/150903, 2017, A1. Location in patent: Page/Page column 21 [12] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 11, p. 3262 - 3271 [13] MedChemComm, 2017, vol. 8, # 2, p. 471 - 478 [14] Bioorganic and medicinal chemistry letters, 2002, vol. 12, # 12, p. 1599 - 1602 [15] Bioscience, Biotechnology and Biochemistry, 2002, vol. 66, # 10, p. 2236 - 2238 [16] Patent: US5234946, 1993, A [17] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1984, # 7, p. 1621 - 1626 [18] Journal of Medicinal Chemistry, 2017, vol. 60, # 14, p. 6384 - 6399 [19] Patent: WO2010/42998, 2010, A1. Location in patent: Page/Page column 98 [20] Journal of Medicinal Chemistry, 1997, vol. 40, # 7, p. 1075 - 1089 [21] Farmaco, 2003, vol. 57, # 11, p. 909 - 916 [22] Journal of Fluorine Chemistry, 2003, vol. 119, # 2, p. 141 - 149 [23] Archiv der Pharmazie, 2017, vol. 350, # 5, [24] Phytochemistry (Elsevier), 1982, vol. 21, # 11, p. 2663 - 2668 [25] Journal of Medicinal Chemistry, 1998, vol. 41, # 15, p. 2745 - 2753 [26] Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 16, p. 2205 - 2208 [27] Bioorganic and Medicinal Chemistry Letters, 2002, vol. 12, # 7, p. 1013 - 1015 [28] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 1, p. 47 - 50 [29] Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 5, p. 2697 - 2706 [30] Patent: WO2005/66194, 2005, A1. Location in patent: Page/Page column 196-197 [31] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 21, p. 6004 - 6008 [32] European Journal of Medicinal Chemistry, 2011, vol. 46, # 9, p. 4227 - 4237 [33] Journal of Enzyme Inhibition and Medicinal Chemistry, 2011, vol. 26, # 5, p. 643 - 648 [34] Patent: US2014/37564, 2014, A1. Location in patent: Paragraph 0314-0315 [35] Chemistry - An Asian Journal, 2015, vol. 10, # 4, p. 925 - 937 [36] Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 14, p. 3218 - 3230 [37] European Journal of Medicinal Chemistry, 2017, vol. 125, p. 1193 - 1199 [38] Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 12, p. 3145 - 3157
产率：83% 合成条件：With potassium phosphate; copper(l) iodide; 1,10-Phenanthroline In 1,4-dioxane at 80℃; Schlenk technique 实验步骤：一般步骤：在烘箱干燥的Schlenk管中，加入醇1（69.0-199.5mg，0.5mmol），CuI（10mol％）和1,10-菲咯啉（20mol％）和K3PO4（2mmol），然后加入二恶烷（2mL）在室温下在露天气氛下。将搅拌的反应混合物在80℃的油浴中加热7-48小时。通过TLC监测反应进程直至反应完成。然后，将反应混合物冷却至室温，用NH4Cl水溶液淬灭，然后用CH2Cl2（3×10mL）萃取。用饱和NaCl溶液洗涤有机层，干燥（Na2SO4），并过滤。在减压下蒸发溶剂并通过硅胶柱色谱法（石油醚/乙酸乙酯）纯化粗材料，得到醛/酮2（61-97％）。 参考文献：[1] Archiv der Pharmazie, 2007, vol. 340, # 5, p. 244 - 250 [2] Tetrahedron, 2006, vol. 62, # 14, p. 3389 - 3394 [3] Synthetic Communications, 2014, vol. 44, # 14, p. 2076 - 2087 [4] Bioorganic and medicinal chemistry letters, 2002, vol. 12, # 14, p. 1791 - 1793
产率：98% 合成条件：With potassium carbonate In ethanol for 6 h; Reflux 实验步骤：将3-羟基苯甲醛（3g，24.59mmol），苄基氯（4.1mL，35.79mmol）和无水K2CO3（2.4g，17.39mmol）在无水EtOH（30mL）中的混合物回流6小时。然后将反应混合物浓缩至干，重新溶解在10mL CH2Cl2中并用5％NaOH水溶液（3×10mL）洗涤。用无水Na2SO4干燥有机层并蒸发至干。通过硅胶柱色谱法（己烷/ EtOAc，8：2）纯化残余物，得到5.1g 3-苄氧基 - 苯甲醛（98％），为白色固体。熔点：54-56℃; 1H NMR（300MHz，CDCl3）：δ= 9.85（s，1H，CHO），7.32（m，9H，H-2，H-4，H-5，H-6，Ph），5.11（s，2H，OCH2Ph）; 13C NMR（75MHz，CDCl3）δ192.5（CHO），159.7（C-3），138.2（C-1），136.7（C-1'），130.5（CH-5），129.1（CH-3'，CH-5'），128.6（CH-4'），127.9（CH-2'，CH-6'），124.1（CH-6），122.6（CH-4），113.6（CH-2），70.6（OCH2Ph）; ESMS m/z（百分比）：213（100）[M + 1] +。 参考文献：[1] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 22, p. 6589 - 6597,9 [2] Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 15, p. 1971 - 1974 [3] Bioorganic and Medicinal Chemistry, 2005, vol. 13, # 5, p. 1537 - 1544 [4] Tetrahedron, 1992, vol. 48, # 35, p. 7185 - 7196 [5] Tetrahedron, 1992, vol. 48, # 5, p. 819 - 830 [6] Patent: US6552080, 2003, B1 [7] Angewandte Chemie - International Edition, 2018, vol. 57, # 19, p. 5325 - 5329 [8] Angew. Chem., 2018, vol. 130, # 19, p. 5423 - 5427,5 [9] European Journal of Medicinal Chemistry, 2017, vol. 133, p. 365 - 378 [10] Journal of the Chemical Society, 1957, p. 513 [11] Journal of Biological Chemistry, 1957, vol. 225, p. 269,275 [12] Journal of the Chemical Society, 1935, p. 1533,1543 [13] Journal of the Chemical Society, 1965, p. 3645 - 3660 [14] Heterocycles, 1988, vol. 27, # 9, p. 2185 - 2196 [15] Bioorganic and Medicinal Chemistry Letters, 1996, vol. 6, # 8, p. 941 - 944 [16] Farmaco, 2003, vol. 57, # 11, p. 909 - 916 [17] Journal of Medicinal Chemistry, 2002, vol. 45, # 23, p. 5058 - 5068 [18] Biochimie, 2013, vol. 95, # 4, p. 842 - 849 [19] European Journal of Medicinal Chemistry, 2013, vol. 68, p. 385 - 393