124931-85-7

Basic information

• Product Name: (4-Chloro-phenyl)-acetic acid 2'-hydroxy-[1,1']binaphthalenyl-2-yl ester
• CAS NO: 124931-85-7
• Molecular Weight: 438.91
• Mol File: 124931-85-7.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (4-Chloro-phenyl)-acetic acid 2'-hydroxy-[1,1']binaphthalenyl-2-yl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (4-Chloro-phenyl)-acetic acid 2'-hydroxy-[1,1']binaphthalenyl-2-yl ester(124931-85-7)
• EPA Substance Registry System: (4-Chloro-phenyl)-acetic acid 2'-hydroxy-[1,1']binaphthalenyl-2-yl ester(124931-85-7)

Safety Data

• Hazardous Substances Data: 124931-85-7(Hazardous Substances Data)

Upstream product

• 1878-66-6 4-chlorophenylacetic Acid 
• 18531-99-2 (S)-[1,1']-binaphthalenyl-2,2'-diol 

Downstream Products

• 124932-02-1 (R)-2-(4-Chloro-phenyl)-3-methyl-butyric acid 2'-hydroxy-[1,1']binaphthalenyl-2-yl ester 
• 124932-02-1 (S)-2-(4-Chloro-phenyl)-3-methyl-butyric acid 2'-hydroxy-[1,1']binaphthalenyl-2-yl ester 
• 132353-58-3 (R)-2-(4-Chloro-phenyl)-propionic acid 2'-hydroxy-[1,1']binaphthalenyl-2-yl ester 
• 132353-58-3 (S)-2-(4-Chloro-phenyl)-propionic acid 2'-hydroxy-[1,1']binaphthalenyl-2-yl ester 
• 55332-38-2 S-isopropyl-4-chlorophenylacetic acid 

Relevant articles and documents

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.