Author(s):
Mesquita, Katiúcia Daiane
Date: 2020
Origin: Oasisbr
Subject(s): CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA; Síntese de Sulfetos; Selenetos Graxos Quirais; Óleo de Mamona; Sulphide Synthesis; Chiral Fatty Selenides; Castor oil; CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA; CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA; Síntese de Sulfetos; Síntese de Sulfetos; Selenetos Graxos Quirais; Selenetos Graxos Quirais; Óleo de Mamona; Óleo de Mamona; Sulphide Synthesis; Sulphide Synthesis; Chiral Fatty Selenides; Chiral Fatty Selenides; Castor oil; Castor oil
Description
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Buscando atender alguns princípios da Química Verde, no presente trabalho foram sintetizados novos compostos organocalcogênios derivados de fonte renovável, como o óleo de mamona. Os 12-organilcalcogenooctadec-9- enoatos de alquila foram obtidos partindo de uma reação de transesterificação do óleo de mamona 1, seguida de tosilação da hidroxila do ricinoleato de metila 2 e posterior substituição nucleofílica com íons calcogenolatos, gerando sulfetos 5 e selenetos graxos quirais 7 (Esquema 1). Esta rota sintética se mostrou eficiente para a síntese de sulfetos e selenetos graxos quirais com bons rendimentos e com a possibilidade de apresentar atividade biológica.
In order to contemplate some of the principles of Green Chemistry, in this study new organochacogen compounds derived from renewable sources, such as castor oil were synthesized. The alkyl 12-organylchalcogenoctadec-9-enoates were obtained starting from a transesterification reaction of castor oil 1, followed by tosylation of hydroxyl group of methyl ricinoleate 2 and subsequent nucleophilic substitution with chalcogenolate anions affording fatty chiral sulfides 5 and selenides 7 (Scheme 1). This proved to be efficient synthetic route for the synthesis of fatty chiral sulfides and selenides with good yields with potential application in biological studies.
