7782-24-3

Usage

InChI:InChI=1/C9H10O2/c1-7(9(10)11)8-5-3-2-4-6-8/h2-7H,1H3,(H,10,11)/t7-/m1/s1

Upstream product

• 31508-44-8 2-phenylpropionic acid methyl ester 
• 28645-07-0 (S)-methyl 2-phenylpropanoate 
• 33662-99-6 2-chloroethyl 2-phenylpropionate 
• 79121-16-7 (S,S)-Hydratropasaeure-1-phenylester 
• 1823-91-2 (S)-α-phenylpropionitrile 
• 68258-25-3 3-Phenyl-1,2-butanediol 
• 55019-72-2 (+)-(S)-p-nitrophenyl α-phenylpropionate 
• 3156-07-8 methyl phenyl ketene 
• 144789-14-0 allyl (S)-2-phenylpropanoate 
• 25145-43-1 2-phenylpropionyl chloride 
• 67-63-0 isopropyl alcohol 
• 176438-84-9 C₁₃H₁₆O₄ 
• 1823-91-2 1-phenylethyl cyanide 
• 2510-99-8 ethyl 2-phenylpropanoate 

Downstream Products

• 28645-07-0 (S)-methyl 2-phenylpropanoate 
• 103088-97-7 (S)-2-phenyl-heptan-3-one 
• 65248-43-3 (S)-2-phenyl-3-hexanone 
• 2627-86-3 (S)-1-phenyl-ethylamine 
• 87786-35-4 2-bromo-2-phenyl-propionic acid 
• 3527-63-7 (S)-2-cyclohexylpropanoic acid 
• 23406-52-2 (S)-2-phenylpentan-3-one 
• 13490-74-9 S(+)-2-phenyl-propanoic acid amide 
• 103130-62-7 (2S)-2-phenylpentan-3-one 
• 25145-43-1 (2S)-2-phenylpropionyl chloride 
• 55019-72-2 (+)-(S)-p-nitrophenyl α-phenylpropionate 
• 127146-19-4 (S)-2-Phenyl-propionic acid (Z)-(S)-2-fluoro-3-phenyl-1-(toluene-4-sulfonylmethyl)-allyl ester 
• 142793-65-5 (S)-2-Phenyl-propionic acid (1R,2R)-2-fluoro-1-p-tolylsulfanylmethyl-pent-4-enyl ester 
• 95617-49-5 Z-Phe-gGly-D-COCH(CH₃)C₆H₅ 

Relevant academic research and scientific papers

Enantioselective oxidation of (±)-2-phenyl-1-propanol to (S)-2-phenyl-1-propionic acid with Acetobacter aceti: Influence of medium engineering and immobilization

The enantioselective oxidation of (RS)-2-phenyl-1-propanol to (S)-2-phenylpropionic acid catalysed by Acetobacter aceti occurred under very mild conditions. The rate, substrate tolerance and enantioselectivity (enantiomeric ratio, E >200) can be increased

The Mechanism and Stereochemistry of Asymmetric Transformation via Chiral Oxazolines

The stereoselectivity of asymmetric transformation of 2-substituted alkanoic acid via oxazolines was clarified by measuring the isomeric ratio of 13C-labeled lithio oxazolines by 13C NMR.The mechanism of the process was discussed fro

Enantioselective oxidation of (RS)-2-phenyl-1-propanol to (S)-2-phenylpropanoic acid with Gluconobacter oxydans: Simplex optimization of the biotransformation

The microbial oxidation of racemic 2-phenyl-1-propanol by Gluconobacter oxydans DSM 50049 was investigated. Whole bacterial cells were used to produce (S)-(+)-2-phenylpropanoic acid with high enantiomeric excess (E>200). A simplex sequential method was em

Optimization of the chiral inversion of 2-phenylpropionic acid by Verticillium lecanii

Previous studies have demonstrated that Verticillium lecanii might be used as a microbial model of the inversion of 2-arylpropionic acids in man. This paper describes the optimization of the inversion process in respect of culture medium, pH, cell density and substrate concentration. The study demonstrates that optimum inversion occurs in Sorensen's phosphate buffer at pH 5.5. The extent and rate of inversion were also shown to be dependent on substrate concentration and cell density. This study will form the basis of the development of a microbial model of the metabolism of 2-arylpropionic acids which might be suitable for the in-vitro screening of new compounds in this class.

Experimental and Model Studies on Continuous Separation of 2-Phenylpropionic Acid Enantiomers by Enantioselective Liquid-Liquid Extraction in Centrifugal Contactor Separators

Multistage enantioselective liquid-liquid extraction (ELLE) of 2-phenylpropionic acid (2-PPA) enantiomers using hydroxypropyl-β-cyclodextrin (HP-β-CD) as extractant was studied experimentally in a counter-current cascade of centrifugal contactor separators (CCSs). Performance of the process was evaluated by purity (enantiomeric excess, ee) and yield (Y). A multistage equilibrium model was established on the basis of single-stage model for chiral extraction of 2-PPA enantiomers and the law of mass conservation. A series of experiments on the extract phase/washing phase ratio (W/O ratio), extractant concentration, the pH value of aqueous phase, and the number of stages was conducted to verify the multistage equilibrium model. It was found that model predictions were in good agreement with the experimental results. The model was applied to predict and optimize the symmetrical separation of 2-PPA enantiomers. The optimal conditions for symmetric separation involves a W/O ratio of 0.6, pH of 2.5, and HP-β-CD concentration of 0.1 mol L-1 at a temperature of 278 K, where eeeq (equal enantiomeric excess) can reach up to 37% and Yeq (equal yield) to 69%. By simulation and optimization, the minimum number of stages was evaluated at 98 and 106 for eeeq > 95% and eeeq > 97%. Chirality 28:235-244, 2016.

Enantioselective Synthesis of Chiral Carboxylic Acids from Alkynes and Formic Acid by Nickel-Catalyzed Cascade Reactions: Facile Synthesis of Profens

We report a stereoselective conversion of terminal alkynes to α-chiral carboxylic acids using a nickel-catalyzed domino hydrocarboxylation-transfer hydrogenation reaction. A simple nickel/BenzP* catalyst displayed high activity in both steps of regioselective hydrocarboxylation of alkynes and subsequent asymmetric transfer hydrogenation. The reaction was successfully applied in enantioselective preparation of three nonsteroidal anti-inflammatory profens (>90 % ees) and the chiral fragment of AZD2716.

Efficient Assay for the Detection of Hydrogen Peroxide by Estimating Enzyme Promiscuous Activity in the Perhydrolysis Reaction

Hydrogen peroxide is an ideal oxidant in view of its availability, atom economy, or green aspects. Furthermore, it is produced by the cell mitochondria and plays a meaningful role in controlling physiological processes, but its unregulated production leads to the destruction of organs. Due to its diverse roles, a fast and selective method for hydrogen peroxide detection is the major limitation to preventing the negative effects caused by its excess. Therefore, we aimed to develop an efficient assay for the detection of H2O2. For this purpose, we combined the enzymatic method for the detection of hydrogen peroxide with the estimation of the promiscuity of various enzymes. We estimated the activity of an enzyme in the reaction of p-nitrophenyl esters with hydrogen peroxide resulting in the formation of peracid. To our knowledge, there is no example of a simple, multi-sensor demonstrating the promiscuous activity of an enzyme and detecting hydrogen peroxide in aqueous media.

Reshaping the active pocket of esterase Est816 for resolution of economically important racemates

Bacterial esterases are potential biocatalysts for the production of optically pure compounds. However, the substrate promiscuity and chiral selectivity of esterases usually have a negative correlation, which limits their commercial value. Herein, an efficient and versatile esterase (Est816) was identified as a promising catalyst for the hydrolysis of a wide range of economically important substrates with low enantioselectivity. We rationally designed several variants with up to 11-fold increased catalytic efficiency towards ethyl 2-arylpropionates, mostly retaining the initial substrate scope and enantioselectivity. These variants provided a dramatic increase in efficiency for biocatalytic applications. Based on the best variant Est816-M1, several variants with higher or inverted enantioselectivity were designed through careful analysis of the structural information and molecular docking. Two stereoselectively complementary mutants, Est816-M3 and Est816-M4, successfully overcame and even reversed the low enantioselectivity, and several 2-arylpropionic acid derivatives with highEvalues were obtained. Our results offer potential industrial biocatalysts for the preparation of structurally diverse chiral carboxylic acids and further lay the foundation for improving the catalytic efficiency and enantioselectivity of esterases.

Palladium-Catalyzed Asymmetric Markovnikov Hydroxycarbonylation and Hydroalkoxycarbonylation of Vinyl Arenes: Synthesis of 2-Arylpropanoic Acids

Asymmetric hydroxycarbonylation is one of the most fundamental yet challenging methods for the synthesis of carboxylic acids. Herein, we reported the development of a palladium-catalyzed highly enantioselective Markovnikov hydroxycarbonylation of vinyl arenes with CO and water. A monodentate phosphoramidite ligand L6 plays vital role in the reaction. The reaction tolerates a range of functional groups, and provides a facile and atom-economical approach to an array of 2-arylpropanoic acids including several commonly used non-steroidal anti-inflammatory drugs. The catalytic system has also enabled an asymmetric Markovnikov hydroalkoxycarbonylation of vinyl arenes with alcohols to afford 2-arylpropanates. Mechanistic investigations suggested that the hydropalladation is irreversible and is the regio- and enantiodetermining step, while hydrolysis/alcoholysis is probably the rate-limiting step.

Cobalt-Catalyzed Asymmetric Hydrogenation of α,β-Unsaturated Carboxylic Acids by Homolytic H2 Cleavage

The asymmetric hydrogenation of α,β-unsaturated carboxylic acids using readily prepared bis(phosphine) cobalt(0) 1,5-cyclooctadiene precatalysts is described. Di-, tri-, and tetra-substituted acrylic acid derivatives with various substitution patterns as well as dehydro-α-amino acid derivatives were hydrogenated with high yields and enantioselectivities, affording chiral carboxylic acids including Naproxen, (S)-Flurbiprofen, and a d-DOPA precursor. Turnover numbers of up to 200 were routinely obtained. Compatibility with common organic functional groups was observed with the reduced cobalt(0) precatalysts, and protic solvents such as methanol and isopropanol were identified as optimal. A series of bis(phosphine) cobalt(II) bis(pivalate) complexes, which bear structural similarity to state-of-the-art ruthenium(II) catalysts, were synthesized, characterized, and proved catalytically competent. X-band EPR experiments revealed bis(phosphine)cobalt(II) bis(carboxylate)s were generated in catalytic reactions and were identified as catalyst resting states. Isolation and characterization of a cobalt(II)-substrate complex from a stoichiometric reaction suggests that alkene insertion into the cobalt hydride occurred in the presence of free carboxylic acid, producing the same alkane enantiomer as that from the catalytic reaction. Deuterium labeling studies established homolytic H2 (or D2) activation by Co(0) and cis addition of H2 (or D2) across alkene double bonds, reminiscent of rhodium(I) catalysts but distinct from ruthenium(II) and nickel(II) carboxylates that operate by heterolytic H2 cleavage pathways.