Benzophenone derivatives containing five-membered heterocycle and preparation method and application of benzophenone derivatives
A technology of benzophenone and five-membered heterocyclic rings, which is applied in the field of benzophenone derivatives, can solve problems such as easy yellowing, easy volatilization, and small molecule migration, and achieve enhanced photostability, mild reaction conditions, and increased The effect of utilization
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Embodiment 1
[0026] Add 0.214g (1mmol) of 2,4-dihydroxybenzophenone and 0.150g (1.5mmol) of triethylamine to the container, dissolve it with 3ml of dichloromethane, and slowly add 0.261g (2mmol) under ice-water bath conditions. ) of 2-furoyl chloride, stirred and reacted for 12 hours. After the reaction, add water to the reaction solution and extract with ethyl acetate, collect the organic phase, wash with water, dry over anhydrous sodium sulfate, and remove the organic solvent by rotary evaporation; and use petroleum ether and ethyl acetate (volume ratio 3:1) as The eluent was separated by column chromatography to obtain 2-hydroxy-4-furanoyloxybenzophenone (derivative 1) and 2,4-bisfuranoyloxybenzophenone (derivative 2).
[0027] Derivative 1: white solid, yield: 46%, m.p.93-96°C. 1 H NMR (600MHz, CDCl 3 )δ12.47–12.22(m,1H),7.69(dd,J=25.5,11.6Hz,4H),7.65–7.59(m,1H),7.54(dd,J=18.7,11.3Hz,
[0028] 2H),7.44(s,1H),7.00(d,J=18.8Hz,1H),6.81(d,J=8.7Hz,1H),6.66(d,J=20.2Hz,1H). 13 C NMR (151M...
Embodiment 2
[0031] Add 0.214g (1mmol) of 2,4-dihydroxybenzophenone and 0.150g (1.5mmol) of triethylamine into the container, dissolve it with 3ml of dichloromethane, and slowly add 0.292g (2mmol) under ice-water bath conditions. ) of 2-thiophenoyl chloride, stirred and reacted for 12 hours. After the reaction, add water to the reaction solution and extract with ethyl acetate, collect the organic phase, wash with water, dry over anhydrous sodium sulfate, and remove the organic solvent by rotary evaporation; and use petroleum ether as the eluent for column chromatography to obtain 2-hydroxy - 4-thienoyloxybenzophenone (derivative 3) and 2,4-bisthienoyloxybenzophenone (derivative 4).
[0032] Derivative 3: white solid, yield: 36%, m.p.83-85°C. 1 H NMR (600MHz, CDCl 3 )δ12.43–12.16(m,1H),8.02(s,1H),7.76–7.66(m,4H),7.66–7.59(m,1H),7.54(dd,J=15.6,8.3Hz,2H) ,7.25–7.19(m,1H),6.98(d,J=16.8Hz,1H),6.81(t,J=12.8Hz,1H). 13 C NMR (151MHz, CDCl 3 )δ200.82, 164.83, 159.64, 156.56, 137.78, 135.27, 13...
Embodiment 3
[0036] Embodiment 3: Derivative 1 is used in the performance evaluation of ultraviolet absorber
[0037] Experimental recipe:
[0038]
[0039] Working conditions:
[0040] Add 50g of epoxy propylene carboxylic acid resin, 44g of 1,6-hexanediol diacrylate, 3g of photoinitiator (1173), 2g of triethanolamine, 2-hydroxyl-4-furyl methyl in the glass container equipped with stirrer 1g of acyloxybenzophenone, stirred to disperse uniformly and transparently, and stand still for 5-10 minutes to obtain a transparent free radical photocurable coating. The paint is divided into three parts, one part is put into a transparent glass bottle and covered for daily indoor storage; the other part is put into a transparent glass bottle and covered with a cover for indoor dark storage; one part is coated on a glass plate with a brush, and the film The thickness is 75 μm, and then cured by a UV curing instrument at a speed of 5 meters per minute (about 5 seconds of light time).
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