Hydroxytyrosol hexamethylene carbamate and synthesis method and application thereof
A technology of alcohol hexamethylene dicarbamate and hydroxytyrosol, which is applied in the field of hydroxytyrosol hexamethylene dicarbamate and its synthesis, can solve problems such as oxidation, irritating odor, and quality deterioration, and achieves the preparation method Simple, prevents oxidation and discoloration, and enhances the effect of anti-oxidation performance
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Embodiment 1
[0027] Put 139mg (0.90mmol) of hydroxytyrosol and 3.7mg (0.03mmol) of DMAP in a 100mL reactor, add 50mL of toluene to fully dissolve it, and then pass it under nitrogen protection. Dissolve 50 mg (0.30 mmol) of 1,6-hexamethylene diisocyanate in 5 mL of toluene, slowly drip into the reaction solution with a separatory funnel, and reflux at 108° C. for 8 h after the addition is complete. TLC traces the reaction to completion, stops heating, and removes the protective device. The reaction mixture system is concentrated under reduced pressure to obtain crude hydroxytyrosol hexamethylene dicarbamate. The crude product was further separated and purified by silica gel column chromatography. Petroleum ether: ethyl acetate=1:5 was used as the eluent. The eluent was concentrated and dried under reduced pressure to obtain 62.26 mg of crude hydroxytyrosol hexamethylene dicarbamate. The total yield was 43.55%.
[0028] 1 H-NMR (400MHz, DMSO- d 6 ) δ (ppm): 8.43 (2H, s), 6.90 (2H, s), 6.86~6...
Embodiment 2
[0030] Put 139mg (0.90mmol) of hydroxytyrosol and 42μL (0.30mmol) of triethylamine in a 100mL reactor, add 50mL of toluene to fully dissolve it, and then pass it under nitrogen protection. Dissolve 50 mg (0.30 mmol) of 1,6-hexamethylene diisocyanate in 5 mL of toluene, slowly drip into the reaction solution with a separatory funnel, and reflux at 108° C. for 6 h after the addition is complete. TLC traces the reaction to completion, stops heating, and removes the protective device. The reaction mixture system is concentrated under reduced pressure to obtain crude hydroxytyrosol hexamethylene dicarbamate. The crude product was further separated and purified by silica gel column chromatography. Petroleum ether: ethyl acetate=1:5 was used as the eluent. The eluent was concentrated and dried under reduced pressure to obtain 53.18 mg of crude hydroxytyrosol hexamethylene dicarbamate. The total yield is 37.20%.
Embodiment 3
[0032] 116mg (0.75mmol) of hydroxytyrosol and 3.7mg (0.03mmol) of DMAP were placed in a 100mL reactor, 50mL of toluene was added to fully dissolve, and then nitrogen protection was introduced. Dissolve 50 mg (0.30 mmol) of 1,6-hexamethylene diisocyanate in 5 mL of toluene, slowly drip into the reaction solution with a separatory funnel, and reflux at 60° C. for 8 hours after the addition is complete. TLC traces the reaction to completion, stops heating, and removes the protective device. The reaction mixture system is concentrated under reduced pressure to obtain crude hydroxytyrosol hexamethylene dicarbamate. The crude product was further separated and purified by silica gel column chromatography, petroleum ether: ethyl acetate=1:5 as the eluent, and the eluent was concentrated and dried under reduced pressure to obtain 56.47 mg of crude hydroxytyrosol hexamethylene dicarbamate. The total yield is 39.50%.
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