14367-67-0

Basic information

• Product Name: Benzenepropanoic acid, a-methyl-, (R)-
• CAS NO: 14367-67-0
• Molecular Formula: C10H12O2
• Molecular Weight: 164.204
• Mol File: 14367-67-0.mol
• Article Data: 129

Chemical Properties

• CAS DataBase Reference: Benzenepropanoic acid, a-methyl-, (R)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenepropanoic acid, a-methyl-, (R)-(14367-67-0)
• EPA Substance Registry System: Benzenepropanoic acid, a-methyl-, (R)-(14367-67-0)

Safety Data

• Hazardous Substances Data: 14367-67-0(Hazardous Substances Data)

Upstream product

• 92053-30-0 (R)-2-benzyl-1-[(S)-2-(2-hydroxypropan-2-yl)pyrrolidin-1-yl]propan-1-one 
• 100-39-0 benzyl bromide 
• 1009-67-2 2-methyl-3-phenylpropanoic acid 
• 123-62-6 propionic acid anhydride 
• 187332-12-3 (4S)-4-(4-hydroxybenzyl)-1,3-oxazolidin-2-one 
• 34917-00-5 2-benzyl-2-methylmalonic acid 
• 1895-97-2 2-methyl-3-phenylacrylic acid 
• 155956-27-7 (2'R,3'R,5R)-(-)-1-(3'-hydroxy-2'-methyl-3'-phenyl-1'-oxopropyl)-3,3,5-trimethyl-2-pyrrolidinone 
• 140479-60-3 (E)-(R)-2-Hydroxy-3-methyl-4-phenyl-but-3-enoic acid isopropyl ester 
• 72040-67-6 4-nitrophenyl (S)-α-methyl-β-phenylpropionate 
• 620-05-3 iodomethylbenzene 
• 92053-21-9 (S)-1-<2-(1-Hydroxy-1-methylethyl)pyrrolidin-1-yl>propan-1-on 
• 92053-24-2 (S)-2-benzyl-1-[(S)-2-(2-hydroxypropan-2-yl)pyrrolidin-1-yl]propan-1-one 
• 159345-08-1 (S)-N-((1S,2S)-1-hydroxy-1-phenylpropan-2-yl)-N,2-dimethyl-3-phenylpropanamide 

Downstream Products

• 29393-16-6 methyl (2R)-2-methyl-3-phenylpropanoate 
• 38574-62-8 methyl (S)-(+)-2-benzylpropionate 
• 51-64-9 dexamfetamine 
• 38385-67-0 (2S)-2-Methyl-3-phenylpropanoic acid chloride 
• 79863-06-2 (-)-(R)-methylbenzylacetohydroxamic acid 
• 96183-46-9 (2S,4S)-2,4-bis(diphenylphosphino)pentane 
• 186900-67-4 (R)-3-cyclohexyl-2-methylpropanoic acid 
• 1416465-79-6 C₁₇H₂₄BrNO 
• 1416465-80-9 C₁₇H₂₄BrNO 
• 22436-06-2 2-methyl-3-phenylpropanol 
• 65-85-0 benzoic acid 
• 29393-16-6 methyl 2-methyl-3-phenylpropionate 
• 159345-12-7 (2R)-1,3-diphenyl-2-methyl-propan-1-one 
• 74669-82-2 (R)-2,3 -dimethyl-4-phenylbutan-2-ol 

Relevant articles and documents

Highly efficient asymmetric hydrogenation of α,β-unsaturated carboxylic acids catalyzed by ruthenium(II)-dipyridylphosphine complexes

Two types of catalysts [RuL(benzene)Cl]Cl and Ru(OCOCH3) 2L with the dipyridylphosphine ligands P-Phos and Xyl-P-Phos were applied in the asymmetric hydrogenation of α,β-unsaturated carboxylic acids. The cationic complexes [RuL(benzene)Cl]Cl were found to be superior to the corresponding neutral complex Ru(OCOCH3)2L in this type of reactions. The catalysts exhibited excellent activities and enantioselectivities (up to 97% ee) in the asymmetric hydrogenation.

L-Valinol and L-phenylalaninol-derived 2-phenylamino-2-oxazolines as chiral auxiliaries in asymmetric alkylations

Lithium enolates of N-acyl phenyliminooxazolidine auxiliaries reacted with alkyl halides to produce the α-alkylated products with very high diastereofacial selectivity (up to >99% d.e.). The products were readily cleaved by simple alkaline hydrolysis to give homochiral carboxylic acids and could also be directly converted to aldehydes and other acid derivatives such as esters and amides.

Model Studies on the Enzyme-Regulated Stereodivergent Cascade Passerini Reaction

The synthesis of chiral α-acyloxy carboxamides containing two stereogenic centers continues to be a challenging field of organic chemistry. Herein, we have proposed and proved the feasibility of an enzyme regulated-cascade reaction, which using the same substrates enables the formation of individual stereoisomers of α-acyloxy carboxamides with up to 99 % ee. The access to the individual stereoisomeric products has been achieved by a combination of the enzymatic kinetic resolution of racemic vinyl esters, subsequent Passerini reaction, and enzymatic kinetic resolution of formed α-acyloxy carboxamides. The presented studies are promising in exploratory proof-of-concept of enzyme-controlled stereodivergent cascade to form an important class of chiral compounds for medicinal chemistry.

Electrocatalytic asymmetric hydrogenation of α,β-unsaturated acids in a PEM reactor with cinchona-modified palladium catalysts

We have developed an electrocatalytic asymmetric hydrogenation reaction using a proton-exchange membrane (PEM) reactor that employs a polymer electrolyte fuel cell and industrial electrolysis technologies. Reasonable enantioselectivities and excellent current efficiencies were obtained in the asymmetric hydrogenation of α-phenylcinnamic acid under mild conditions without adding a supporting electrolyte. The current density was crucial to achieving the improved results observed.