知识与财富的链接
以3,5-二甲氧基苯甲醛、对甲氧基苄醇为原料,经合成硫醚和砜的中间产物,再利用Ramberg-Backlund反应将砜转化为反式碳碳双键,最后脱去甲基获得白藜芦醇。研究探讨了反应条件对硫醚氧化和对Ramberg-Backlund反应的影响。结果表明,在以H2O2-SeO2为氧化剂,CH3OH为溶剂的条件下,硫醚的氧化效果最佳,砜的产率可达82%;在以CCl4-KOH作为卤化试剂,V(正丁醇)∶V(水)=6∶1的正丁醇-水作为溶剂的条件下,Ramberg-Backlund反应的效果最好,反式双键产物的产率为84%。该合成路线总产率为41%。产物及各中间体的结构经1H(13C)NMR、IR和ESI-MS确证。
Resveratrol was synthesized from 3,5-dimethoxylbenzaldehyde and 4-methoxybenzyl alcohol via thioetherification,thioether oxidation,Ramberg-Bcklund reaction and demethylation.The conditions of thioether oxidation and Ramberg-Bcklund reaction were discussed and optimized.The results indicate that the thioether oxidation had the best result in CH3OH solvent using H2O2-SeO2 as oxidant and 82% yield of sulphone was obtained.The Ramberg-Bcklund reaction showed a good stereoselectivity with 84% yield of E isomer in n-C4H9OH-H2O(volume ratio 6∶1) with CCl4-KOH halogenating agent.The total yield of resveratrol of this synthetic route reached as high as 41%.The structures of the target compound and key intermediates were verified by means of 1H(13C)NMR,IR and ESI-MS.
