Acetylphloroglucinol compounds and their application in the preparation of antibacterial drugs
A technology of acetylphloroglucinol and compounds, which is applied in the preparation of organic compounds, antibacterial drugs, carboxylic acid amides, etc., can solve the problems of increased difficulty in analysis and stability, complex structures of natural products, etc., and achieve good inhibition Active, good antibacterial effect
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Embodiment 1
[0023] Embodiment 1: 3-acetylphloroglucinol formic acid ( 2 ) preparation
[0024]
[0025] Weigh 1.70 g (0.01 mol) of 2,4,6-trihydroxybenzoic acid into a 50 mL three-neck flask, stir in an ice bath, slowly add 1.53 g (0.015 mol) of acetic anhydride and 3.77 mL of (4.25 g) boron trifluoride-diethyl ether solution (contains boron trifluoride 0.06 mol). After 24 h, the reaction was stopped, and 10 mL of distilled water was added under stirring, extracted with 10 mL × 3 ethyl acetate, washed with saturated brine (10 mL × 2), dried and concentrated. After separation by silica gel column chromatography (eluent: petroleum ether / ethyl acetate = 3:1), 3-acetylphloroglucinol formic acid (1.46 g) was obtained with a yield of 69%. 1 H NMR (400 MHz, DMSO- d 6 ): δ (ppm) 2.52 (s, 3H, COCH 3 ), 6.06 (s, 1H, ArH), 9.69 (s, 2H, OH), 10.52 (s, 1H, OH), 12.25 (s, 1H, COOH); 13 C NMR (100 MHz, DMSO- d 6 ): δ 34.2, 102.8, 104.5, 112.6, 162.7, 164.9, 169.3, 173.8, 202.4; MS (ESI) m / z :...
Embodiment 2
[0026] Embodiment 2: 3-acetylphloroglucinol formic acid-phenol ester ( 3a ) preparation
[0027]
[0028] Dissolve 2.12 g (0.01 mol) of 3-acetylphloroglucinol formic acid in 20 mL of dichloromethane, add 1.88 g (0.02 mol) of phenol after complete dissolution, and then add 0.50 g (0.004 mol) of N,N- Dimethylaminopyridine (DMAP) and 3.84 g (0.02 mol) 1-ethyl-(3-dimethylaminopropyl) carbodiimide (EDC) were reacted at room temperature for 3 h. The reaction solution was poured into 50 mL of water, extracted twice with ethyl acetate, dried over anhydrous magnesium sulfate, the solvent was removed under reduced pressure, and separated by silica gel column chromatography (eluent: petroleum ether / ethyl acetate = 5:1). 2.16 g of the target compound was obtained with a yield of 75%. 1 H NMR (400 MHz, DMSO- d 6 ): δ (ppm) 2.47 (s, 3H, COCH 3 ), 6.30 (s, 1H, ArH), 7.32-7.41 (m, 5H, ArH), 9.79 (s, 1H, OH), 9.85 (s, 1H, OH), 11.60 (s, 1H, OH); 13 C NMR (100 MHz, DMSO- d 6 ): δ 34....
Embodiment 3
[0029] Embodiment 3: 3-acetylphloroglucinol formic acid-4-(methyl)phenol ester ( 3b ) preparation
[0030]
[0031] Dissolve 2.12 g (0.01 mol) of 3-acetylphloroglucinol formic acid in 20 mL of dichloromethane, add 2.16 g (0.02 mol) of 4-methylphenol after complete dissolution, and then add 0.50 g (0.004 mol) N,N-Dimethylaminopyridine (DMAP) and 3.84 g (0.02 mol) 1-ethyl-(3-dimethylaminopropyl) carbodiimide (EDC) were reacted at room temperature for 3 h. The reaction solution was poured into 50 mL of water, extracted twice with ethyl acetate, dried over anhydrous magnesium sulfate, the solvent was removed under reduced pressure, and separated by silica gel column chromatography (eluent: petroleum ether / ethyl acetate = 5:1). 1.90 g of the target compound was obtained with a yield of 63%. 1 H NMR (400 MHz, DMSO- d 6 ): δ (ppm) 2.18 (s, 3H, CH 3 ), 2.40 (s, 3H, COCH 3 ), 6.38 (s, 1H, ArH), 7.05 (d, 2H, J =8.0 Hz, ArH), 7.18 (d, 2H, J =8.0 Hz, ArH), 9.70 (s, 1H, OH), 9.8...
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