Synthesis And Characterization Of Acetyl Acetate Compounds

Stilbene compounds usually refer to general terms of dithienylethene and its derivatives. The structure feature of this kind of compounds is that it contains a conjugated system of dithienylethene.Resveratrol is a kind of natural product which was earliest discovered and deepest researched by scientists, and which versatile functional and widely applicable in stilbene compounds. The representative compound (resveratrol) and its derivatives have diverse biological activities, such as:inhibiting microbes, eliminateing ree radicals, inhibiting tumor, anti-thrombus as well as preventing and curing heart disease, hyperlipidemia, cardiovascular disease and so on. Therefore, the research and applicable development have been one of highlights for this kind of natural active ingredients. Due to limited contents and supplying level from natural plant resources, and more extraction process complex with high cost, the styrene compounds far cannot satisfy the increasing demand of market home and abroad. Therefore, the preparation and synthesis of this kind of biological active ingredients from simple and easy starting materials are attracting more people’s attention. And it is expected that to obtain the biological active ingredients with new structure and high activity by modification of structure and reconstruction.The paper reported the preparation of the phosphonium halogenides, which were synthesized by following reaction steps:firstly, choosing substituted-benzoic acid or substituted-benzyl alcohol as raw materials; secondly, carrying out the phenolic hydroxyl methylation and reduction of carboxyl or ester group, chlorination of the corresponding compounds; lastly, the substituted-benzyl triphenyl phosphonium salts were obtained through nucleophilic substitution of the substituted benzyl chloride with triphenylphosphine.Following, the corresponding phosphorus ylides were smoothly prepared from the catalytic reaction with the action of alkali in situ. The carbon-carbon double bonds ware builded and the target compounds ware successfully synthesized by the typical Wittig reaction of the corresponding phosphorus ylides with furfural, thiophenecar- boxal, and other substituted benzaldehyde.The39stilbenes ware synthesized totally. They included121-substituted phenyl-2-fuan ethylenes (i.e.10a,10b,11a,11b,12a,13b,14a,15a,15b,25,26,27),131-substituted phenyl-2-thiophene ethylenes (i.e.16a,16b,17a,17b,18a,19a,19b,20b,21a,22a,23a,24a,24b) and14substituted stilbenes (28-41). Among them,10compounds have been not published in literatures (i.e.10a,10b,12a,13b,14a,19a,19b,20b,24a,24b). However, It should be pointed out that the compound25,26and27were mixtures of trans/cis configuration).Experimental results showed that most of them were trans-stilbenes, and minority cis-stilbene under the reaction condition selected. Their whole yields could achieve30～80%. All of the structures of the synthesized compounds were confirmed and characterizated by1H-NMR,13C-NMR, FT-IR and MS.