146912-66-5

Basic information

• Product Name: (R)-2-hydroxy-4-oxo-4-phenylbutanoic acid
• Synonyms: (R)-2-hydroxy-4-oxo-4-phenylbutanoic acid
• CAS NO: 146912-66-5
• Molecular Weight: 194.187
• Mol File: 146912-66-5.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: (R)-2-hydroxy-4-oxo-4-phenylbutanoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-2-hydroxy-4-oxo-4-phenylbutanoic acid(146912-66-5)
• EPA Substance Registry System: (R)-2-hydroxy-4-oxo-4-phenylbutanoic acid(146912-66-5)

Safety Data

• Hazardous Substances Data: 146912-66-5(Hazardous Substances Data)

Upstream product

• 6296-54-4 ethyl 2,4-dioxo-4-phenylbutyrate 
• 244277-48-3 ethyl (R)-(-)-2-hydroxy-4-oxo-4-phenylbutanoate 
• 14189-99-2 (R)-(+)-2-acetoxysuccinic anhydride 
• 71-43-2 benzene 
• 159974-68-2 (R)-3,4-dihydroxy-1-phenylbutan-1-one 
• 156386-82-2 trans-γ-3-benzoylprop-2-en-1-ol 
• 1005327-17-2 (R)-1-phenyl-2-(2-phenyl-1,3,2-dioxaborolan-4-yl)ethanone 
• 98-86-2 acetophenone 

Downstream Products

• 29678-81-7 (R)-2-hydroxy4-phenylbutanoic acid 
• 90315-82-5 ethyl (R)-2-hydroxy-4-phenylbutyrate 
• 109010-59-5 (R)-2-<(4-nitrobenzolsulfonyl)oxy>-4-phenylbuttersaeure-ethylester 
• 86541-77-7 (3S)-1-(carboxymethyl)-<<(1S)-1-(ethoxycarbonyl)-3-phenylpropyl>amino>-2,3,4,5-tetrahydro-1H-<1>benzazepin-2-one hydrochloride 
• 143615-31-0 (2R)-4-phenylbutane-1,2-diol 

Relevant articles and documents

Enantio- and regiospecific reduction of ethyl 4-phenyl-2,4-dioxobutyrate with baker's yeast: Preparation of (R)-HPB ester

Ethyl 2,4-dioxo-4-phenylbutyrate obtained by condensation of acetophenone with diethyl oxalate is reduced enantio- and regiospecifically by baker's yeast in a diisopropyl ether/water two-phase system to give (-)-ethyl (R)-2-hydroxy-4-oxo-4-phenylbutyrate with an ee = 98% in 80% isolated yield. The hydroxyester was hydrogenated over Pd-C to obtain (-)-ethyl (R)-2-hydroxy-4-phenylbutyrate (HPB ester), an important intermediate for the synthesis of ACE inhibitors. Prolonged contact of the reduction product with baker's yeast produced 3-phenyl 3-oxo propanol in 90% yield.

Chloramphenicol base chemistry. Part 10: Asymmetric synthesis of α-hydroxy chiral alcohols via intramolecular Michael additions of γ-hydroxy-α, β-unsaturated enones with chloramphenicol base derived bifunctional urea organocatalysts

We have developed the chloramphenicol base urea-catalyzed intramolecular Michael addition of γ-hydroxy-α, β-unsaturated enones. The oxidation of the resulting products provided facile access to the corresponding α-hydroxy chiral alcohols with good efficiency and enantioselectivity, with the reaction displaying broad substrate scope. The utility of this methodology was further demonstrated by the synthesis of (R)-2-hydroxy-4-phenylbutanoate, which is a key building block for the construction of the ACE inhibitor benazepril hydrochloride.

Stereoselective routes to chiral 2-hydroxy-4-oxo acids and substituted 2-hydroxybutyrolactones using lactate dehydrogenases

The enantioselective reduction 2,4-dioxo acids catalysed by lactate dehydrogenases provided access to 2-hydroxy-4-oxo acids of both S and R configuration. Subsequent diastereoselective chemical reduction affords 4-substituted 2-hydroxybutyrolactones.