Selective Reduction of Dimedone
نویسنده
چکیده
The selective hydrogenation of dimedone (1) to the corresponding monoketone 2 over palladium and Amberlyst 15 ® is reported. The product is a synthetic building block for the fragrance and pharmaceutical industry. Advantages of the new catalytic procedure are the high catalyst activity and selectivity, less by-product formation, avoidance of the presence of acid, and consequently, less salt formation due to the omission of a neutralization step. Using a substrate/catalyst ratio of >100 compound 2 can be synthesized in 97% yield at full conversion. Recycling of the catalyst several times has been shown to be feasible without any detectable decrease in selectivity.
منابع مشابه
Cysteine perthiosulfenic acid (Cys-SSOH): A novel intermediate in thiol-based redox signaling?☆
The reversible oxidation of protein cysteine residues (Cys-SH) is a key reaction in cellular redox signaling involving initial formation of sulfenic acids (Cys-SOH), which are commonly detected using selective dimedone-based probes. Here, we report that significant portions of dimedone-tagged proteins are susceptible to cleavage by DTT reflecting the presence of perthiosulfenic acid species (Cy...
متن کاملMeasurement of protein sulfenic acid content.
Protein sulfenic acids are reactive, reversibly oxidized cysteinyl residues with roles in redox catalysis and regulation. Detection and quantification of these species in proteins is accomplished through chemical modification by reagents such as 7-chloro-4-nitrobenzo-2-oxa-1,3-diazole (NBD chloride), 2-nitro-5-thiobenzoate (TNB), dimedone, or derivatives of dimedone, followed by UV-visible spec...
متن کاملSynthesis of some derivatives of dimedone, gamma pyrone and barbituric acid.
Aim: Dimedone , gamma pyrone and barbituric acid and their derivatives have also been found to be very important from their application point of view. Thus our aim was to prepare more derivatives from them. Method : Dimedone , gamma pyrone and barbituric acid have been treated with dimethyl sulphoxide and acetic anhydride reagent under varying temperature conditions in order to get more compoun...
متن کاملReductive alkylation of active methylene compounds with carbonyl derivatives, calcium hydride and a heterogeneous catalyst.
A one-pot two-step reaction (Knoevenagel condensation - reduction of the double bond) has been developed using calcium hydride as a reductant in the presence of a supported noble metal catalyst. The reaction between carbonyl compounds and active methylene compounds such as methylcyanoacetate, 1,3-dimethylbarbituric acid, dimedone and the more challenging dimethylmalonate, affords the correspond...
متن کاملIdentification of dimedone-trapped sulfenylated proteins in plants under stress
In stressed plants, the reactive oxygen species (ROS) levels rise. Key to ROS signaling research are detection and identification of the protein cysteine sulfenylation (-SOH), the ROS-mediated oxidative product of a thiol (-SH). Arabidopsis thaliana seedlings were stressed with hydrogen peroxide (H2O2) and the sulfenylated proteins were tagged with dimedone. Dimedone-tagged sulfenic acid protei...
متن کامل