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Study On Synthesis And Activitiy Of Natural Benzopranylchalcone

Posted on:2018-06-11Degree:MasterType:Thesis
Country:ChinaCandidate:M J NiuFull Text:PDF
GTID:2321330518987792Subject:Organic Chemistry
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This study describes the synthesis and activity of chalcone,finishes one Dihydrochalcone 1 and three Benzopyran chalcone sythesis;studies the photooxidation properties of Sanjuanolide sythesis.The paper includes four parts as follows:1.The properties of chalcone compounds,the structure and preparation method of singlet oxygen in photocatalytic reaction were summarized.2.The total synthesis and biological activity experiment of 1-(5,7-dihydroxy-2,2-dimethylchroman-6-yl)-3-(2,2-dimethylchroman-6-yl)propan-1-oneThe total synthetic of 1-(5,7-dihydroxy-2,2-dimethylchroman-6-yl)-3-(2,2-dimethylchroman-6-yl)propan-1-one was achieved through benzopyran,protection of phenolic hydroxyl group,aldol condensation,Pd-C/H2 reduction and deprotection starting from cheap 2,4,6-trihydroxyacetophenone and 4-hydroxybenzaldehyde and the preliminary bioassay indicated that compound had good activity of Gram-negative bacteria(Escherichia coli)rang in 64 ?g/mL-3 2 pg/mL.3.Total synthesis and biological activity experiment of three Benzopyran chalconesThe total synthetic of FleminginB,FleminginM,FleminginN was achieved through acetylation demethylation,benzopyran,protection of phenolic hydroxyl group,sharpless asymmetric dihydroxylation,aldol condensation deportection starting from cheap sesamol;The preliminary bioassay indicated that FleminginM showed significant bacteriostatic effect on Gram-negative bacteria(Escherichia coli)at 256 ?g/mL and FleminginN showed significant bacteriostatic effect on Gram-positive bacteria(Staphylococcus aureus)at 256,g/mL,FleminginM,FleminginN non-corresponding isomers had antibacterial activity against two representative bacteria.4.Study on Synthesis of sanjuanolideThe natural product of Sanjuanolide was designs total synthesis.In the synthesis process,photocatalytic reaction of singlet oxygen was the significant step reaction.Because thermochemical reaction had due low yield,complicated product,separation difficult and structural instability.We have made a simple study on the application of photooxidation in synthesis.It was found that the olefinic structure produced by the reaction of olefins in the photooxidation of olefins was extremely unstable and was easily deteriorated during the reaction,so the optimum reaction conditions were obtained.
Keywords/Search Tags:Benzopyran chalcone, antibacterial activity, photocatalysis, total synthesis
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