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The Impatient Chemical Composition And Steroidal Chlorinated Research

Posted on:2008-05-31Degree:MasterType:Thesis
Country:ChinaCandidate:L H TianFull Text:PDF
GTID:2204360215460426Subject:Organic Chemistry
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This thesis includes two parts of work. The first part is the studies of chemical constituents of the seeds of impatiens balsamina L., which is an important folk herbal medicine.1.The chemical constituents of the seeds of impatiens balsamina L..have been investigated. By using various chromatogrm nine compounds have been isolated from the alcohol extract of the seeds,they were elucidated by NMR, MS, IR, et al. The structural of the compounds were: Kaempferol (1), Kaempferol-3-O-α-L-rhamnoside (2), Kaempferol-3 -glucoside(3), Quercetin (4), Quercetin-3-O-P-D- glucoside(5), 14-Deoxy-ll,12-didehydroandrographolide (6), Stigmasterol(7), Sucrose (8),α-Ethyl-D- glucoside (9) .Six compounds were isolated from the plant for the first time,which were 1,2,3,5,6 and 7.2.We have found that anhydrous ferric chloride could chlorinate 3β-hydroxyl-5-△steroids to afford corresponding alkyl chlorides with retention of configuration. This is first use of anhydrous ferric chloride in chlorination of steroids. The treatment of the solution of DHEA in methylenechloride with an equivalent amount of anhydrous ferric chloride at room temperature, stirred for five hours , DHEA disappeared , afforded the main product 10 by-product 11. they were elucidated by NMR, MS, IR, et al. In order to further investigate the features of the reaction,DHEA was reacted with FeC13 under different conditions. The notable features of this procedure are mild reaction conditions, high selectivity, reasonable yields and operational simplicity. The possible mechanism for the chlorination has been proposed. This new method has not been reported in the literatures.
Keywords/Search Tags:Impatiens balsamina L., flavonoid, 3β-hydroxyl-5-△steroids, mechanism
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