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Studies On The Synthesis Of Trifloxystrobin Derivatives And Mono-6-[(S)-pyrrolidine-2-carbo Xamide]-β-cyclodextrin

Posted on:2008-07-29Degree:MasterType:Thesis
Country:ChinaCandidate:G Y LuFull Text:PDF
GTID:2121360212981001Subject:Organic Chemistry
Abstract/Summary:PDF Full Text Request
In this dissertation the following two sections are included.1. Studies on the synthesis of trifloxstrobin derivatives.Trifloxystrobin which is a new class of fluoro-fungicides derived from strobilurin possesses high activity against a wide variety of fungi and low toxicity to people. In this paper, based on trifloxystrobin, we add a containing-fluorine function or heterocycle including nitrogen atom to trifloxstrobin in order to enhance its antibacterial activity. The derivatives were obtained by using dimethyl benzene as raw material followed by steps of F-C reaction, oxidation with potassium permanganate in alkaline solution, esterification with methanol, reaction with methoxyamine, bromization with NBS and condensation with (E)-1-(3-(trifluoromethyl) phenyl) ethanone oxime. All the products were characterized by 1HNMR, 13CNMR, MASS and AA (Atom Analyzer). We also conducted some studies on the effect of each reaction's parameters on product synthesis.2. mono-6-[(S)-pyrrolidine-2-carboxamide]-β-cyclodextrinBased on recent studies about chemical modification of β -cyclodextrin, we modified the position 6 on the β -cyclodextrin molecular with L-proline which is a universal asymmetric catalyst. To synthesis the derivative of β -cyclodextrin is to obtain a better asymmetric catalyst and develop the physical characteristics of β -cyclodextrin. In this paper, mono-6-[(S)-pyrrolidine-2-carboxamide]- β -cyclodextrin was obtained by using the β -cyclodextrin as raw material followed by steps of reaction with p-toluenesulfonyl chloride, substitution with azidosodium, reduction, condensation with N-Boc-L-proline, and de-Boc with TFA (trifluoroacetic acid).
Keywords/Search Tags:Fungicide, Trifloxstrobin, Strobilurin, β-cyclodextrin, L-proline
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