52779-90-5

Upstream product

• 52780-18-4 [4-(thiophene-2-carbonyl)-phenyl]-acetonitrile 
• 73899-15-7 1-(t-butyldimethylsilyloxy)-2-(4-bromophenyl)ethane 
• 4654-39-1 4-bromophenethanol 
• 173593-53-8 {4-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-phenyl}-thiophen-2-yl-methanol 
• 98-03-3 thiophene-2-carbaldehyde 

Downstream Products

• 132353-67-4 [4-(2-Thiophen-2-yl-[1,3]dioxolan-2-yl)-phenyl]-acetic acid 
• 40828-46-4 2-[4-(thien-2-ylcarbonyl)phenyl]propanoic acid 
• 57931-92-7 3-(dimethylamino)propyl p-(2-thenoyl)hydratropate oxalate 
• 57931-91-6 2-(dimethylamino)ethyl p-(2-thenoyl)hydratropate oxalate 
• 52780-02-6 2-(diethylamino)ethyl p-(2-thenoyl)hydratropate hydrochloride 
• 52779-97-2 p-(2-thenoyl)hydratropic acid, sodium salt 
• 52780-10-6 2-[4-(thiophene-2-carbonyl)-phenyl]-propionamide 
• 52780-07-1 4'-chloro-4-(2-thenoyl)hydratropanilide 
• 52780-05-9 N-phenyl-2-[4-(thiophene-2-carbonyl)-phenyl]-propionamide 
• 57931-90-5 propyl p-(2-thenoyl)hydratropate 
• 52780-11-7 N-hydroxy-2-[4-(thiophene-2-carbonyl)-phenyl]-propionamide 
• 52779-95-0 ethyl p-(2-thenoyl)hydratropate 
• 52841-36-8 2-[4-(2-thienylcarbonyl)phenyl]propanoic acid methyl ester 
• 52780-20-8 α-methyl-4-(2-thienylcarbonyl)benzeneacetyl chloride 

Relevant academic research and scientific papers

1,1′-binaphthalene-2,2′-diol as a chiral auxiliary. Diastereoselective alkylation of binaphthyl esters, complex-induced proximity effects in enolate formation, and one-step synthesis of an optically active β-substituted ketone

Diastereoselective alkylation of enolates derived from (S)-naphthyl phenylacetate 1 with LDA in THF gave the S,S-isomer as a major product. The diastereoselectivity increased as the bulkiness of the alkylating agent was increased. The low diastereomeric excess (～70%) of methylation was markedly raised to 92% by the use of n-BuLi as a base due to the complex-induced proximity effect (CIPE) in enolate formation. This highly diastereoselective methylation was used to synthesize the clinically important anti-inflammatory drugs (S)-naproxen (60) and (S)-suprofen (68). The stereochemistry of ketene trimethylsilyl acetals generated from several phenylacetates was investigated to understand the origin of the diastereoselectivity in this alkylation. Methyl phenylacetate (46) predominantly gave a (Z)-enolate by kinetic deprotonation, while the (E)-enolate was predominantly obtained from phenyl phenylacetate (47). An optically active ketone (88) was synthesized from binaphthyl ester 84 by a one-pot procedure involving the 1,4-addition, followed by the 1,2-addition, of organometallics. The CIPE again played a crucial role in the high enantiomeric excess in this case.

Complex-induced proximity effects in enolate formation. Highly diastereoselective α-methylation of binaphthyl esters of arylacetic acids

Highly diastereoselective methylation of binaphthyl esters of arylacetic acids and its application to the syntheses of antiinflammatory drugs, (S)-suprofen and (S)-naproxen.

Aroyl-substituted phenylacetic acid derivatives

Compounds of the class of aroyl-substituted phenylacetic acids and corresponding esters, amides and hydroxamic acids, useful as anti-inflammatory agents and certain novel precursors therefor.

Synthesis of α methyl 4 (2 thienylcarbonyl)benzeneacetic acid, suprofen, and derivatives

A series of compounds with general structure Het CO Ar CH(CH3)COOH was prepared for pharmacological screening. Different synthetic approaches are described. α Methyl 4 (2 thienylcarbonyl)benzeneacetic acid (compound III-l, suprofen), was found to show a marked antiwrithing activity. Furthermore this compound proved to be a potent inhibitor of prostaglandin biosynthesis.