262429-49-2

Usage

Uses

Used in Organic Synthesis:
(R)-3-AMINO-3-(3-CHLORO-PHENYL)-PROPIONIC ACID is used as a building block in the synthesis of various organic compounds and materials. Its unique structure and functional groups allow for the creation of new chemicals with potential applications in various industries.
Used in Pharmaceutical Industry:
(R)-3-AMINO-3-(3-CHLORO-PHENYL)-PROPIONIC ACID is used as an intermediate in the development of pharmaceutical compounds. Its chiral nature and functional groups can be leveraged to create enantiomerically pure drugs with improved efficacy and reduced side effects.
Used in Chemical Research:
(R)-3-AMINO-3-(3-CHLORO-PHENYL)-PROPIONIC ACID serves as a valuable research tool in the study of chiral chemistry, stereochemistry, and the development of asymmetric synthesis methods. Its unique structure provides insights into the behavior of chiral molecules and their interactions with biological systems.
Used in Material Science:
(R)-3-AMINO-3-(3-CHLORO-PHENYL)-PROPIONIC ACID can be utilized in the design and synthesis of novel materials with specific properties, such as chiral polymers, chiral catalysts, or chiral sensors. Its incorporation into these materials can lead to enhanced performance and selectivity in various applications.

InChI:InChI=1/C9H10ClNO2/c10-7-3-1-2-6(4-7)8(11)5-9(12)13/h1-4,8H,5,11H2,(H,12,13)/t8-/m1/s1

Upstream product

• 1866-38-2 m-Chlorocinnamic acid 
• 587-04-2 m-Chlorobenzaldehyde 
• 68208-21-9 3-amino-3-(3-chloro-phenyl)-propionic acid 
• 2039-85-2 3-Chlorostyrene 
• 262429-48-1 (+/-)-N-Phenylacetyl-3-(3-chlorophenyl)-β-alanine 

Relevant academic research and scientific papers

Enantioselective acylation of β-phenylalanine acid and its derivatives catalyzed by penicillin G acylase from alcaligenes faecalis

This study developed a simple, efficient method for producing racemic β-phenylalanine acid (BPA) and its derivatives via the enantioselective acylation catalyzed by the penicillin G acylase from Alcaligenes faecalis (Af-PGA). When the reaction was run at 25°C and pH 10 in an aqueous medium containing phenylacetamide and BPA in a molar ratio of 2:1, 8 U/mL enzyme and 0.1 M BPA, the maximum BPA conversion efficiency at 40 min only reached 36.1%, which, however, increased to 42.9% as the pH value and the molar ratio of phenylacetamide to BPA were elevated to 11 and 3:1, respectively. Under the relatively optimum reaction conditions, the maximum conversion efficiencies of BPA derivatives all reached about 50% in a relatively short reaction time (45-90 min). The enantiomeric excess value of product (eep) and enantiomeric excess value of substrate (ees) were all above 98% and 95%, respectively. These results suggest that the method established in this study is practical, effective, and environmentally benign and may be applied to industrial production of enantiomerically pure BPA and its derivatives.

Phenylalanine aminomutase-catalyzed addition of ammonia to substituted cinnamic acids: A route to enantiopure α- and β-amino acids

(Chemical Equation Presented) An approach is described for the synthesis of aromatic α- and β-amino acids that uses phenylalanine aminomutase to catalyze a highly enantioselective addition of ammonia to substituted cinnamic acids. The reaction has a broad scope and yields substituted α- and β-phenylalanines with excellent enantiomeric excess. The regioselectivity of the conversion is determined by substituents present at the aromatic ring. A box model for the enzyme active site is proposed, derived from the influence of the hydrophobicity of substituents on the enzyme affinity toward various substrates.

A new route to enantiopure β-aryl-substituted β-amino acids and 4-aryl-substituted β-lactams through lipase-catalyzed enantioselective ring cleavage of β-lactams

A simple and efficient direct enzymatic method was developed for the synthesis of 4-aryl-substituted β-lactams and the corresponding β-amino acid enantiomers through the CAL-B (lipase B from Candida antarctica)-catalyzed enantioselective (E > 200) ring cleavage of the corresponding racemic β-lactams with 1 equiv. of H2O in i-Pr2O at 60°C. The product (R)-β-amino acids (ee ≥ 98%, yields ≥ 42%) and unreacted (S)-β-lactams (ee ≥ 95%, yields ≥ 41%) could be easily separated. The ring opening of enantiomeric β-lactams with 18% HCl afforded the corresponding enantiopure β-amino acid hydrochlorides (ee ≥ 99%).

Efficient synthesis of 2-aryl-6-methyl-2,3-dihydro-1H-pyridin-4-ones

Syntheses of 2-aryl-6-methyl-2,3-dihydro-1H-pyridin-4-ones were achieved starting from corresponding β-arylβ-amino acids. This reaction sequence involved, as a key step, the condensation of an acid chloride with a diketone using SmI3 as catalyst. A final intramolecular cyclization furnished the attempted product. (C) 2000 Elsevier Science Ltd.