1798-60-3

Usage

Uses

Used in Pharmaceutical Synthesis:
(R)-1-hydroxy-1-phenylacetone is used as an intermediate in the synthesis of Pseudoephedrine and Ephedrine, which are important pharmaceutical compounds with various medical applications, such as treating nasal congestion and attention deficit hyperactivity disorder (ADHD).
Used in Antibacterial and Antifungal Applications:
(R)-1-hydroxy-1-phenylacetone is used as a reagent in the preparation of chiral (amino)alkanol derivatives, which are then evaluated for their activity as antibacterial and antifungal agents. This application highlights its potential in the development of new drugs to combat bacterial and fungal infections.

InChI:InChI=1/C9H10O2/c1-7(10)9(11)8-5-3-2-4-6-8/h2-6,9,11H,1H3/t9-/m0/s1

Upstream product

• 100-52-7 benzaldehyde 
• 127-17-3 2-oxo-propionic acid 
• 57-50-1 Sucrose 
• 917-64-6 methyl magnesium iodide 
• 120443-82-5 (R)-2-phenyl-2-(trimethylsiloxy)acetonitrile 
• 43108-63-0 1-phenyl-2-trimethylsiloxy-1-propene 
• 42722-80-5 (α-methoxyvinyl)lithium 
• 75-07-0 acetaldehyde 
• 103-79-7 1-phenyl-acetone 
• 579-07-7 1-Phenylpropane-1,2-dione 
• 201738-82-1 (Z)-1-phenyl-2-tert-butyldimethylsiloxy-1-propene 
• 2327-99-3 1-phenylpropadiene 
• 5910-25-8 3-phenylpentane-2,4-dione 
• 19275-80-0 (R)-2-oxo-1-phenylpropyl acetate 

Downstream Products

• 299-42-3 ephedrine 
• 492-41-1 (1R,2S)-norephedrine 
• 14838-15-4 u-2-amino-1-phenylpropan-1-ol 
• 55253-39-9 (R)-1-hydroxy-1-phenylpropan-2-one oxime 
• 107055-45-8 (R)-3-methyl-2-phenyl-1-oxa-4-aza-spiro[4.5]dec-3-ene 
• 19275-80-0 (R)-2-oxo-1-phenylpropyl acetate 
• 7624-24-0 (R)-1-methoxy-1-phenyl-acetone 
• 97432-02-5 2-(2-cyclohexyl-3-methyl-morpholin-4-ylamino)-1-phenyl-propan-1-ol 
• 97432-04-7 2-(3-methyl-2-phenyl-morpholin-4-ylamino)-1-phenyl-propan-1-ol 
• 40421-52-1 (1R,2S)-1-phenylpropane-1,2-diol 
• 40421-51-0 (1R,2R)-1-phenylpropane-1,2-diol 
• 131520-20-2 3,6-diphenyl-1,4-dimethyl-2,5,7-trioxabicyclo<2.2.1>heptane 
• 321-97-1 (1R,2R)-pseudoephedrine 
• 90-63-1 (RS)-1-hydroxy-1-phenylpropan-2-one 

Relevant academic research and scientific papers

Chiral Pt/ZrO2 catalysts. enantioselective hydrogenation of 1-phenyl-1,2-propanedione

The enantioselective hydrogenation of 1-phenyl-1,2-propanedione over Pt colloids stabilized with (R,S)-4,5-dihydro-4,5-diphenyl-2-(6-cyanopyridinyl) imidazoline (CI) supported on a meso-structured ZrO2 under a pressure of 40 bar of H2 at 298 K has been investigated. The metal loading in all catalysts was 1 wt%. The effect of the amount of chiral modifier on the metal particle size and on the catalytic behavior was analyzed. It was found that as the CI/Pt molar ratio increases from 2.5 to 3.5 the Pt crystal size decreases from 3.0 to 1.8 nm. All catalysts were very active in the studied reaction, with the most active one being the catalyst with smaller Pt particles, whereas the selectivity is higher in those catalysts with larger chiral modified Pt metal particles.

Enantioselective hydrogenation of 1-phenyl-1,2-propanodione on cinchonidine-modified Rh/MCM-41 catalysts

Enantioselective hydrogenation of 1-phenyl-1,2-propanodione (PPD) on Rh/MCM-41 catalysts was studied. The catalysts were prepared using Rh(acac) 3 as a metal precursor and metal loadings that ranged from 0.5 to 1.5 wt%. The samples were characterised by nitrogen adsorption-desorption isotherms at 77 K using ICP-MS, XRD, TEM, XRD and XPS. The reaction was performed at 298 K, and 0.01 mol L-1 of PPD and cinchonidine (CD) was used as chiral modifier. The effect of the modifier concentration on the enantioselectivity (ee) and the conversion level in the hydrogenation reaction shows a relationship between the activity and ee as well as the CD concentration. The volcano-type curve observed for each catalyst suggests competitive adsorption of the modifier and substrate on the catalyst surface. The metal loading influences both the Rh crystallite size and catalytic behaviour. An increase in the Rh levels was accompanied by a parallel increase in both the crystallite size and number of Rh ensembles with a subsequent enhancement in both the conversion level and ee. The catalyst with the highest metal loading was 1.0 wt% Rh/MCM-41, and it displayed the highest ee among the catalysts studied. Additionally, the effects of hydrogen pressure and solvent nature on the catalytic activity were also studied. Moreover, the H2 pressure also influenced the conversion levels with only a minor effect on the ee values. Considering the solvent effects, we observed non-linear ee dependence with an increasing solvent dielectric constant, which showed a decrease in conversion levels in the order cyclohexane > toluene > tetrahydrofurane > dichloromethane.

Enantioselective hydrogenation of 1-phenyl-1,2-propanedione over Pt on immobilized cinchonidine on γ-Al2O3 catalysts

Chirally modified γ-Al2O3 containing different amounts of cinchonidine were prepared by the chemical modification of cinchonidine with trimethoxysilane (TMS-CD). These solids were used as support of Pt catalysts containing 1 wt% Pt by chemical reduction of the hexachloroplatinic acid with H2 at 25°C and 40 bar. The characterization was carried out by elemental analysis of C, H and N, TG, DRIFT, NMR 13C and 29Si on solid state, N2 adsorption-desorption at 77 K, XDR, XPS and TEM. The catalytic activity was evaluated in the hydrogenation of 1-phenyl-propane-1,2-dione in a batch reactor at 298 K and 40 bar. The effect of H2 pressure, concentration substrate, catalyst mass, solvents effect and recycles, of the catalyst with the major enantiomeric excess was studied. It was found that all catalysts were active in the reaction being the enantiomeric excess of the target product, 1-R-phenyl-1-hydroxy-2-propanone in the range 30-44% and the best catalyst is that supported on γ-Al2O3 with a nominal content of 5 wt% TMS-CD. The results obtained in this study confirm that the variation of reaction conditions show a dependence on the activity and enantioselectivity for substrate adsorption in the metal active sites. In the solvent effect, enantiomeric excess decreased non-linearly with an increasing solvent dielectric and we could be attributed to the interactions between solvents and TMS-CD in the surface. In the recycles studies enantiomeric excess was achieved as 40% even after 3rd reuse with a slight loss in activity and enantiomeric excess.

Enantioselective hydrogenation of 1-phenyl-1,2-propanedione

Enantioselective hydrogenation of a diketone, 1-phenyl-1,2-propanedione was studied in a pressurized reactor at 5 bar and at 0-25C in different solvents: ethanol, ethyl acetate, and dichloromethane over platinum catalysts. Both in situ modification (simultaneous addition of the reagent and the modifier) and pre-modification (preadsorption of the modifier prior to the reagent) of the catalyst were investigated using cinchonidine as catalyst modifier. Racemic hydrogenation proceeded with nearly the same rate as the selective hydrogenation in the presence of the catalyst modifier. The kinetic results revealed that the hydrogenation of the carbonyl group attached to the phenyl ring was preferred, the main product being 1-hydroxy-1-phenylpropanone; the ratio between 1-hydroxy-1-phenylpropanone and 2-hydroxy-1-phenylpropanone was about 11. The most effective and enantioselective catalyst was obtained by in situ modification in dichloromethane yielding in 67 mol% of (R)-1-hydroxy-1-phenylpropanone, corresponding to the enantiomeric excess of 64%. The enantiomeric excess was independent of the reactant conversion. In the second hydrogenation step the main product among diols was (1R,2S)-1-phenyl-1,2- propanediol.

Enantioselective hydrogenation of 1-phenyl-1,2-propanedione on immobilised cinchonidine-TiO2 catalysts

The enantioselective hydrogenation of 1-phenyl-1,2-propanodione (PPD) was investigated using cinchonidine-immobilised Pt/TiO2 catalysts. Prior to metal deposition, TiO2 was chirally modified by the direct anchoring of cinchonidine (CD) using trimethoxysilane as coupling agent (TMS-CD). The catalysts were prepared using a high H2 pressure reduction-deposition method and were characterised by elemental analysis (C, H and N), TG, DRIFT, 13C and 29Si solid-state NMR, N 2 adsorption-desorption isotherms, XRD, XPS and HR-TEM. The catalytic activity was evaluated in a batch reactor at 298 K and 40 bar using cyclohexane as solvent with various cinchonidine concentrations. The results indicate that the enantioselectivity was sensitive to the CD surface concentration and the enantiomeric excess of the target product, 1-R-phenyl-1-hydroxy-2-propanone, was in the range of 25-51%. The best catalyst was the one supported on TiO 2 with a nominal content of 10 wt% TMS-CD. The effect of the H 2 pressure, the concentration of substrate, solvent and recyclability of the catalyst were studied. The results obtained confirmed that the variation of reaction conditions affects both the activity and enantioselectivity due to the substrate adsorption on the metal active sites. Concerning the solvent effect, the enantiomeric excess decreased non-linearly upon increasing the solvent dielectric constant; this was attributed to the interactions between solvents and TMS-CD on the surface. In the catalyst recycling studies, the enantiomeric excess decreased up to 40% after the 3rd reuse. The drop of activity and enantiomeric excess was attributed to the hydrogenation of the immobilised CD.

Enantioselective hydrogenation of 1-phenyl-1,2-propanodione on Pt/ ZrO 2 catalysts

The enantioselective hydrogenation of 1-phenyl-1,2-propanedione at 298K and pressure of 40 bar of H2 over zirconia supported Pt catalysts has been studied. Three different zirconia were prepared: i) ZrO2- P obtained by a precipitation procedure from ZrOCl2 ii) MSZrO 2 obtained by a sol-gel procedure using cetryltrimethylammonium bromide (CTMABR) as surfactant to get a mesostructured solid iii) CNTsZrO 2 obtained after impregnation of carbon nanotubes with ZrO(NO) 3 followed by pyrolisis and calcination. Pt (1wt%) was introduced on the support by impregnation of an aqueous solution of H2PtCl 6. The catalysts were characterized by nitrogen adsorption-desorption isotherms at 77 K, hydrogen chemisorption, XRD and TEM techniques. The reactions were carried out in a stainless steel batch reactor using cyclohexane as solvent and cinchonidine as chiral modifier. The presence of CD in the reaction medium is necessary to induce an enantiomeric excess (ee) of the desired product R-1phenyl-1 hydroxi-2-propanone. In all the studied systems, the relation between the enantioselectivity and the CD concentration added in situ exhibits a bell type curve; indicative of the importance of competitive adsorption between the modifier and the substrate on the catalyst surface. On the other hand, confinement effect led to an important enhancement in the activity in those catalysts supported on mesostructured supports, mainly in the Pt/CNTsZrO2 catalyst.

Enantioselective hydrogenation of 1-phenyl-propane-1,2-dione on immobilised cinchonidine Pt/SiO2 catalysts

Chirally modified SiO2 containing different amounts of cinchonidine was prepared by the chemical modification of cinchonidine (CD) with trimethoxysilane over SiO2 that had been chemically activated with 1,4-dioxane/HCl. This solid wa

Whole-Cell Biocatalysis in Seawater: New Halotolerant Yeast Strains for the Regio- and Stereoselectivity Reduction of 1-Phenylpropane-1,2-Dione in Saline-Rich Media

The application of green chemistry concepts in catalysis has considerably increased in recent years, and the interest in using sustainable solvents in the chemical industry is growing. One of the recent proposals to fall in line with this is to employ seawater as a solvent in biocatalytic processes. This involves selecting halotolerant strains capable of carrying out chemical conversions in the presence of the salt concentrations found in this solution. Recent studies by our group have revealed the interest in using strains belonging to Debaryomyces and Schwanniomyces for catalytic processes run in this medium. In the present work, we select other yeasts based on their halotolerance to widen the scope of this strategy. We consider them for the monoreduction of 1-phenylpropane-1,2-dione, a well-characterized reaction that produces acyloin intermediates of pharmaceutical interest. The results obtained herein indicate that using seawater as a solvent for this reaction is possible. The best ones were obtained for Saccharomyces cerevisiae FY86 and Kluyveromyces marxianus, for which acyloins with different stereochemistry were obtained with good to excellent enantiomeric excess.

Branched-chain keto acid decarboxylase from Lactococcus lactis (KdcA), a valuable thiamine diphosphate-dependent enzyme for asymmetric C - C bond formation

The thiamine diphosphate-dependent, branched-chain 2-keto acid decarboxylase from Lactococcus lactis sup. cremoris Bl157 (KdcA) is a new valuable enzyme for the synthesis of chiral 2-hydroxy ketones. The gene was cloned and the enzyme was expressed as an

Hydrogenation of 1-phenyl-1,2-propanedione over Pt catalysts modified by cinchona alkaloid O-ethers and the kinetic resolution of the 1-hydroxyketones generated

Nine cinchona alkaloid O-ethers together with cinchonidine and cinchonine were studied as chiral modifiers in the enantioselective hydrogenation of 1-phenyl-1,2-propanedione over Pt/Al2O3. The influence of the O-substituent on the reaction rate, selectivity and product distribution was investigated. Apparent rate constants for all hydrogenation steps were calculated using a first-order kinetic approach resulting in a good agreement between the experimentally recorded and predicted concentrations. The experimentally observed structure-selectivity effects indicate that the mechanisms of enantiodifferentiation over the catalyst modified by parent cinchona alkaloids and their ether derivatives differ from each other. Moreover, the modifier structure-selectivity dependence and the solvent effect were different for enantio- and diastereoselection in the 1-phenyl-1,2-propanedione and 1-hydroxyketone hydrogenations. Correlation between the modifier substituent bulkiness and diastereoselectivity of the 1-hydroxyketone hydrogenation was observed. Data on the inversion of enantioselectivity of 1-phenyl-1,2-propanedione hydrogenation, diastereoselectivity and the sense of kinetic resolution of the 1-hydroxyketones were presented. Due to the complexity of the reaction network, several competing mechanistic pathways may be present in a single reaction system.