52780-12-8

Usage

Uses

Used in Pharmaceutical Synthesis:
(S)-2-[4-(thien-2-ylcarbonyl)phenyl]butyric acid is used as a key building block for the development of nonsteroidal anti-inflammatory drugs (NSAIDs) such as Ibuprofen and Fenoprofen. Its chiral nature and functional groups contribute to the effectiveness of these medications in reducing inflammation and pain.
Used in Agrochemical Development:
In the agrochemical industry, (S)-2-[4-(thien-2-ylcarbonyl)phenyl]butyric acid serves as an essential component in the synthesis of various compounds with pesticidal and herbicidal properties, aiding in the protection and enhancement of crop yields.
Used in Medicinal Research:
Due to its potential anti-inflammatory and antitumor properties, (S)-2-[4-(thien-2-ylcarbonyl)phenyl]butyric acid is utilized in medicinal research for the exploration of novel therapeutic agents. Its structural characteristics allow for the development of bioactive molecules with potential applications in treating various diseases and conditions.
Used in the Preparation of Diverse Bioactive Molecules:
(S)-2-[4-(thien-2-ylcarbonyl)phenyl]butyric acid is employed as a versatile intermediate for the synthesis of a wide range of bioactive molecules. Its functional groups and structural features enable the creation of compounds with diverse biological activities, making it a valuable asset in the field of chemical and pharmaceutical research.

InChI:InChI=1/C15H14O3S/c1-2-12(15(17)18)10-5-7-11(8-6-10)14(16)13-4-3-9-19-13/h3-9,12H,2H2,1H3,(H,17,18)/t12-/m0/s1

Upstream product

• 52841-36-8 2-[4-(2-thienylcarbonyl)phenyl]propanoic acid methyl ester 
• 52779-90-5 4-(thien-2-ylcarbonyl)phenylacetic acid 
• 73899-15-7 1-(t-butyldimethylsilyloxy)-2-(4-bromophenyl)ethane 
• 40828-46-4 2-[4-(thien-2-ylcarbonyl)phenyl]propanoic acid 
• 132353-68-5 [4-(2-Thiophen-2-yl-[1,3]dioxolan-2-yl)-phenyl]-acetic acid 2'-hydroxy-[1,1']binaphthalenyl-2-yl ester 
• 132353-67-4 [4-(2-Thiophen-2-yl-[1,3]dioxolan-2-yl)-phenyl]-acetic acid 
• 4654-39-1 4-bromophenethanol 
• 98-03-3 thiophene-2-carbaldehyde 
• 52780-20-8 α-methyl-4-(2-thienylcarbonyl)benzeneacetyl chloride 
• 132353-69-6 (S)-2-[4-(2-Thiophen-2-yl-[1,3]dioxolan-2-yl)-phenyl]-propionic acid 2'-hydroxy-[1,1']binaphthalenyl-2-yl ester 

Relevant academic research and scientific papers

Enantioselective potential of polysaccharide-based chiral stationary phases in supercritical fluid chromatography

The enantioselective potential of two polysaccharide-based chiral stationary phases for analysis of chiral structurally diverse biologically active compounds was evaluated in supercritical fluid chromatography using a set of 52 analytes. The chiral selectors immobilized on 2.5?μm silica particles were tris-(3,5-dimethylphenylcarmabate) derivatives of cellulose or amylose. The influence of the polysaccharide backbone, different organic modifiers, and different mobile phase additives on retention and enantioseparation was monitored. Conditions for fast baseline enantioseparation were found for the majority of the compounds. The success rate of baseline and partial enantioseparation with cellulose-based chiral stationary phase was 51.9% and 15.4%, respectively. Using amylose-based chiral stationary phase we obtained 76.9% of baseline enantioseparations and 9.6% of partial enantioseparations of the tested compounds. The best results on cellulose-based chiral stationary phase were achieved particularly with propane-2-ol and a mixture of isopropylamine and trifluoroacetic acid as organic modifier and additive to CO2, respectively. Methanol and basic additive isopropylamine were preferred on amylose-based chiral stationary phase. The complementary enantioselectivity of the cellulose- and amylose-based chiral stationary phases allows separation of the majority of the tested structurally different compounds. Separation systems were found to be directly applicable for analyses of biologically active compounds of interest.

(R)- and (S)-3-Hydroxy-4,4-dimethyl-1-phenyl-2-pyrrolidinone, New Chiral Auxiliaries for the Asymmetric Synthesis of α-Arylpropanoic Acids.

Reaction of rac-α-arylpropanoyl chlorides with (R)- and (S)-3-hydroxy-4,4-dimethyl-1-phenyl-2-pyrrolidinone (R)- and (S)-1, in the presence of triethylamine, under standard esterification conditions, gave (R,R)- and (S,S)-3, respectively, with high diastereoselectivity.Controlled acidic hydrolysis afforded the corresponding (R)- or (S)-α-arylpropanoic acids with high enantioselectivity, the chiral auxiliary being recovered efficiently.

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.

Enhancing the enantioselectivity of Candida lipase catalyzed ester hydrolysis via noncovalent enzyme modification

When the lipase of Candida cylindracea was treated with deoxycholate and organic solvents (ether-ethanol, 1:1), the enzyme apparently unfolded and refolded to generate a more stable conformer, termed lipase A-form. This lipase A-form was found to be considerably more enantioselective than the native enzyme toward the hydrolysis of a variety of (±)-arylpropionic and (±)-phenoxypropionic esters.