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目的:白藜芦醇衍生物3,4,5,4’-四羟基二苯乙烯四甲基化物的比较合成研究。方法:以3,4,5-三甲氧基苯甲酸和茴香醛为起始原料,3,4,5-三甲氧基苯甲酸经过Na BH4还原和SOCl2卤代制备成卤代烃,卤代烃经Wittig-Horner反应制备Wittig试剂和Grignard反应制备Grignard试剂。Wittig试剂和Grignard试剂再分别与茴香醛缩合制备3,4,5,4’-四甲氧基二苯乙烯。终产物的结构经由1H-NMR和MS分析确认。结果:经1H-NMR和MS分析确认,采用Wittig-Horner反应和Grignard反应合成3,4,5,4’-四甲氧基二苯乙烯的总得率分别为75.76%、15.96%,二者差异显著。结论:Wittig-Horner反应相对更有利于目标化合物关键步骤中双键的构建,收率较高,成本较低,更适宜目标化合物的全合成。
OBJECTIVE: To compare and synthesize the resveratrol derivatives 3,4,5,4’-tetrahydroxystilbene tetramethylate. Methods: Starting from 3,4,5-trimethoxybenzoic acid and anisaldehyde, 3,4,5-trimethoxybenzoic acid was prepared into halocarbons by Na BH4 reduction and SOCl2 halogenation. Halogenated hydrocarbons Grignard reagent was prepared by Wittig-Horner reaction and Grignard reaction. Wittig reagent and Grignard reagent are respectively condensed with anisaldehyde to prepare 3,4,5,4’-tetramethoxy stilbene. The structure of the final product was confirmed by1H-NMR and MS analysis. Results: The total yield of 3,4,5,4’-tetramethoxy-stilbene synthesized by Wittig-Horner reaction and Grignard reaction was 75.76% and 15.96%, respectively, by 1H-NMR and MS analysis. Significant. Conclusion: The Wittig-Horner reaction is relatively more conducive to the construction of double bonds in the key steps of target compounds with high yield, low cost and more suitable for total synthesis of target compounds.