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Application And Research Of The Synthesis Of ?-nitro Alanine Derivatives By Michael Addition

Posted on:2015-10-22Degree:MasterType:Thesis
Country:ChinaCandidate:N ShengFull Text:PDF
GTID:2381330542995973Subject:Chemical engineering
Abstract/Summary:PDF Full Text Request
Michael addition reaction,one of the most valuable organic synthesis reaction,is a common way to build a carbon-carbon bond,sometimes referred to as 1,4-addition,conjugate addition.Michael addition reaction is the reaction of the nucleophile occurring to ?,?-unsaturated carbonyl compound with ? carbon atoms.In inverse synthetic analysis,Michael addition reaction belongs to reactions nucleophile occuring on a3 synthon.Using different nucleophiles,Michael addition reaction in organic synthesis can easily generate carbon-carbon bonds,carbon-oxygen bonds,carbon-sulfur bonds,carbon and nitrogen bonds,carbon selenium keys,etc.When the Michael addition reaction contacts with aldol reaction,it produces the most famous organic synthesis reaction-Robinson annulation.The latter is the most useful for the synthesis of Wieland-Michelle ketone.This one is the basis of synthetic steroids,also being an important raw material of many synthetic terpene natural products.For example,it can be used for the synthesis of anti-cancer drug Taxol.Based on extensive literature reference,this paper conducted a synthesis of P-nitro-alanine derivatives.This paper used aniline compounds with aromatic groups to nucleophilicly attack nitroolefin with ester structure and simply,efficiently and gently synthesized twenty-seven new structures of ?-nitro-alanine derivatives with an aromatic nitro group.The structure of the target compounds were confirmed by IR,HRMS,1HNMR and 13CNMR.This paper used orthogonal design method for optimization of the synthesis of ?-nitro-alanine derivatives conditions and obtained the optimum reaction conditions.
Keywords/Search Tags:Nitro-alanine derivatives, Michael addition reaction, Secnidazole, Synthesis, Simple and efficient
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