Method for synthesizing β-nitroalcohols catalyzed by lipase in organic phase
A lipase and compound technology, which is applied in the field of lipase-catalyzed synthesis of β-nitroalcohol compounds, can solve the problems of less lyase source, long reaction time, application limitations and the like, and achieves simple operation, mild reaction conditions and high efficiency. synthetic effect
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Embodiment 1
[0031] Example 1 Catalyzed synthesis of 2-nitro-1-(4-nitrophenyl)-propanol in anhydrous dimethyl sulfoxide
[0032]151 g of 4-nitrobenzaldehyde (1 mol) and 150 g of nitroethane (2 mol) were added to dimethyl sulfoxide dehydrated through molecular sieves to form a mixture with a total volume of 1 l. Then, add the porcine pancreatic lipase of 30 grams (300000IU), react at 80 ℃ for 0.5 hour, measure the β-nitroalcohol compound with liquid chromatography: adopt C18 chromatographic column, mobile phase is methanol aqueous solution (the volume of methanol and water The ratio is 35 / 65), the flow rate is 1ml / min, the detection wavelength is 210nm, and the yield is 78%. The product was purified by column chromatography and then characterized by proton nuclear magnetic resonance to confirm the structure. The results are as follows:
[0033] 1 H NMR (CDCl 3 , δ, ppm): 8.26-8.23 (m, 2H), 7.60-7.57 (m, 2H), 5.55-5.54, 5.20-5.17 (m, 1H), 4.78-4.69 (m, 1H), 3.08-3.03 ( d, 1H, J 2.1Hz), 1...
Embodiment 2
[0035] Example 2 Catalyzed synthesis of 2-nitro-1-(4-nitrophenyl)-ethanol in anhydrous dimethyl sulfoxide
[0036] 151 g of 4-nitrobenzaldehyde (1 mol) and 122 g of nitromethane (2 mol) were added to dimethylsulfoxide dehydrated through molecular sieves to form a mixture with a total volume of 1 l. Then, add the porcine pancreatic lipase of 30 grams (300000IU), react at 50 ℃ for 0.5 hour, measure the β-nitroalcohol compound with liquid chromatography: adopt C18 chromatographic column, mobile phase is methanol aqueous solution (the volume of methanol and water Ratio is 10 / 90), flow velocity 1ml / min, detection wavelength 210nm, productive rate is 90%, the product confirms the structure with proton nuclear magnetic resonance spectrum characterization after the product is purified by column chromatography, the result is as follows:
[0037] 1 H NMR (CDCl 3 , δ, ppm): 8.25-8.23 (m, 2H), 7.63-7.61 (m, 2H), 5.62-5.58 (m, 1H), 4.63-4.57 (m, 2H), 3.50-3.46 (m, 1H) .
[0038] The ab...
Embodiment 3
[0039] Example 3 Enzyme-catalyzed synthesis of 2-nitro-1-phenylethanol in anhydrous N,N-dimethylformamide
[0040] 212 g of benzaldehyde (2 mol) and 366 g of nitromethane (6 mol) were added to N,N-dimethylformamide from which water had been removed through molecular sieves to form a mixture with a total volume of 3 l. Then, add the Candida antarctica lipase of 100 grams (1000000IU), react at 40 DEG C for 2 hours, measure the β-nitroalcohol compound productive rate according to the liquid chromatography condition of embodiment 1 and be 76%, product passes column layer After purification by analytical chromatography, the structure was confirmed by proton nuclear magnetic resonance spectroscopy, and the results were as follows:
[0041] 1 H NMR (CDCl 3 , δ, ppm): 7.43-7.38(m, 5H), 5.50-5.46(m, 1H), 4.66-4.51(m, 2H), 2.92-2.91(d, 1H, J 1.8Hz).
[0042] The above results indicated that the synthetic product was 2-nitro-1-phenylethanol.
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