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目的:以活性天然产物牛蒡苷元为原料,合成其脱甲基衍生物,寻找适宜的脱甲基化方法。方法:以牛蒡苷元为底物,分别以无水氯化铝或氢溴酸为脱甲基试剂进行反应,比较两者脱甲基能力,并制备了目标产物。结果:合成了两个牛蒡苷元脱甲基衍生物,其中化合物2是首次利用氢溴酸-冰醋酸系统进行脱甲基反应而制备得到,采用氢溴酸-冰醋酸系统进行脱甲基反应,收率较高,操作简单。结论:牛蒡苷元脱甲基化最佳工艺条件为:以牛蒡苷元为原料,氢溴酸作为脱甲基试剂,在110℃条件下反应8h,收率87%,并通过核磁共振碳谱和氢谱对目标产物进行了结构确证。
OBJECTIVE: To synthesize demethylated derivatives of arctigenin, an active natural product, to find a suitable demethylation method. Methods: Arctigenin was used as substrate to react with anhydrous aluminum chloride or hydrobromic acid as demethylation reagent respectively. The demethylation capacity of the two compounds was compared and the target product was prepared. Results: Two arctigenin demethylated derivatives were synthesized. Among them, compound 2 was first prepared by dehydroxylation with hydrobromic acid - glacial acetic acid system, and demethylation was carried out by hydrobromic acid - glacial acetic acid system The yield is high, easy to operate. CONCLUSION: The optimal conditions for the demethylation of arctigenin were as follows: arctigenin was used as starting material and hydrobromic acid as demethylation reagent was reacted at 110 ℃ for 8 h with a yield of 87% And the structure of the target product was confirmed by proton spectroscopy.