15397-33-8

Usage

Uses

Used in Pharmaceutical Industry:
3-OXO-3-PHENYL-PROPIONALDEHYDE is used as a precursor in the synthesis of various pharmaceuticals for its ability to be chemically modified into a range of medicinal compounds.
Used in Organic Synthesis:
In the field of organic chemistry, 3-OXO-3-PHENYL-PROPIONALDEHYDE is used as a key intermediate for the production of a variety of organic compounds, highlighting its versatility in chemical reactions.
Used in Illicit Drug Production:
Regrettably, 3-OXO-3-PHENYL-PROPIONALDEHYDE is also used as a crucial component in the illegal production of methamphetamine, which underscores the need for strict regulatory control over its distribution and use.

Upstream product

• 607-00-1 diphenylformamide 
• 98-86-2 acetophenone 
• 109-94-4 formic acid ethyl ester 
• 86029-78-9 β-phenylthio-β-trimethylsilylpropiophenone 
• 856070-27-4 3-benzenesulfonyl-3-hydroxy-1-phenyl-propan-1-one 
• 71403-94-6 2,3-epoxy-3-phenylpropanal 
• 70-11-1 α-bromoacetophenone 
• 3623-15-2 phenyl propargyl ketone 
• 13735-81-4 1-styrenyloxytrimethylsilane 
• 41125-10-4 benzoylacetaldehyde sodium salt 
• 107-31-3 Methyl formate 
• 614-20-0 3-oxo-3-phenylpropionic acid 
• 78018-47-0 3,3-trimethylenedithio-1-phenyl-1-propanone 

Downstream Products

• 109722-47-6 2-phenylbenzo[4,5]imidazo[1,2-a]pyrimidine 
• 19181-38-5 7-Phenylpyrido<2,3-d>pyrimidin-2,4-diamin 
• 95769-03-2 2-amino-7-phenyl-3H-pyrido[2,3-d]pyrimidin-4-one 
• 112273-10-6 2-phenyl-naphth[2',3':4,5]imidazo[1,2-a]pyrimidine 
• 15753-61-4 1-phenyl-3-(p-tolylamino)prop-2-en-1-one 
• 1702-14-3 ethyl 2-methyl-6-phenylnicotinate 
• 126382-70-5 benzoylacetaldehyde benzoylhydrazone 
• 5653-29-2 2-(1,3-dithiolan-2-yl)-1-phenylethan-1-one 
• 30091-51-1 5-benzoyl-2-phenylpyridine 
• 30091-50-0 bis-(3-oxo-3-phenyl-propenyl)-amine 
• 3617-16-1 Benzoylacetaldehyde ω-semicarbazone 
• 4677-12-7 3-oxo-3-phenyl-propionaldehyde-(N-phenyl oxime ) 
• 56162-64-2 Ethyl 2-Amino-6-phenyl-3-pyridinecarboxylate 
• 112553-83-0 2-phenylquinolizinium picrate 

Relevant academic research and scientific papers

Characterization of Carboxylic Acid Reductases as Enzymes in the Toolbox for Synthetic Chemistry

Carboxylic acid reductase enzymes (CARs) meet the demand in synthetic chemistry for a green and regiospecific route to aldehydes from their respective carboxylic acids. However, relatively few of these enzymes have been characterized. A sequence alignment with members of the ANL (Acyl-CoA synthetase/ NRPS adenylation domain/Luciferase) superfamily of enzymes shed light on CAR functional dynamics. Four unstudied enzymes were selected by using a phylogenetic analysis of known and hypothetical CARs, and for the first time, a thorough biochemical characterization was performed. Kinetic analysis of these enzymes with various substrates shows that they have a broad but similar substrate specificity. Electron-rich acids are favored, which suggests that the first step in the proposed reaction mechanism, attack by the carboxylate on the α-phosphate of adenosine triphosphate (ATP), is the step that determines the substrate specificity and reaction kinetics. The effects of pH and temperature provide a clear operational window for the use of these CARs, whereas an investigation of product inhibition by NADP+, adenosine monophosphate, and pyrophosphate indicates that the binding of substrates at the adenylation domain is ordered with ATP binding first. This study consolidates CARs as important and exciting enzymes in the toolbox for sustainable chemistry and provides specifications for their use as a biocatalyst.

Chemoselectivity in the reaction of 2-diazo-3-oxo-3-phenylpropanal with aldehydes and ketones

The chemoselectivity in the reaction of 2-diazo-3-oxo-3-phenylpropanal (1) with aldehydes and ketones in the presence of Et3N was investigated. The results indicate that 1 reacts with aromatic aldehydes with weak electron-donating substituents and cyclic ketones under formation of 6-phenyl-4H-1,3-dioxin-4-one derivatives. However, it reacts with aromatic aldehydes with electron-withdrawing substituents to yield 1,3-diaryl-3-hydroxypropan-1-ones, accompanied by chalcone derivatives in some cases. It did not react with linear ketones, aliphatic aldehydes, and aromatic aldehydes with strong electron-donating substituents. A mechanism for the formation of 1,3-diaryl-3-hydroxypropan-1-ones and chalcone derivatives is proposed. We also tried to react 1 with other unsaturated compounds, including various olefins and nitriles, and cumulated unsaturated compounds, such as N,N′-dialkylcarbodiimines, phenyl isocyanate, isothiocyanate, and CS2. Only with N,N′-dialkylcarbodiimines, the expected cycloaddition took place. Copyright

Synthesis of the naphthalenone, dihydroquinoline, and dihydrofuran derivatives

The reactions of enaminones with dimethyl diazomalonate were investigated in the presence of copper(II) acetylacetonate. From the reaction of (E)-3-[methyl(phenyl)amino]-1-phenylprop-2-en-1-one (6c), dimethyl 2-[methyl(phenyl)amino]-4-oxonaphthalene-1,1-(4H)-dicarboxylate, was unexpectedly obtained as the major product. Quinoline derivatives were formed as the major products in the case of N-methyl-p-anisidino and N-methyl-p-toluidino enaminones. The reactions of acetyl enaminones were also realized, and quinoline derivatives were isolated as the major products. 3H- and 5H-dihydrofurans were also formed as side products in these reactions. These results differ from those reported earlier on the reactions of tertiary enaminones with carbenes/metal carbenes.

Synthesis and antibacterial evaluation of novel 4-alkyl substituted phenyl β-aldehyde ketone derivatives

A series of novel 4-alkylphenyl β-aldehyde ketones and their derivatives were designed and synthesized on the basis of the chemical structures of Houttuynin and β-lactam antibiotics. Antibacterial activities of these compounds were investigated. The results demonstrated that most of the compounds tested had moderate antibacterial activities against Gram-positive pathogen Staphylococcus aureus (ATTC-25923) than Houttuynin, and Gram-positive bacteria were more susceptible to the compounds than Gram-negative bacteria. Compound 23 was found to be the most potent compound with MIC of 1.0 μg/mL against S. aureus. Particularly, compounds 16, 22 and 23 showed more active antibacterial activities against the clinically important pathogenic bacteria, methicillin-resistant S. aureus (MRSA) than Houttuynin and levofloxacin. The preliminary structure-activity relationship (SAR) analysis suggested that (1) the introduction of appropriate alkyl substituents into position 4 of phenyl ring enhanced antibacterial activities of these compounds, and isopropyl substituent might be more favorable; (2) the presence of ketone carbonyl moiety might play a vital role in determining significant antibacterial activities of these compounds.

Identification and optimisation of 5-amino-7-aryldihydro-1,4-diazepines as 5-HT2A ligands

A several series of low molecular weight 5-HT2A leads were identified from an analysis of HTS data, the exploration of SAR and optimization of one series using parallel synthesis are described, affording compound 22 (5-HT2A IC50 1.1 nM).

Ionic liquid as reagent. A green procedure for the regioselective conversion of epoxides to vicinal-halohydrins using [AcMIm]X under catalyst- and solvent-free conditions

A variety of structurally diverse epoxides undergo facile cleavages by ionic liquid, [AcMIm]X without any catalyst and solvent to produce the corresponding vicinal halohydrins in high yields. The cleavages are considerably fast and highly regioselective.

Flash vacuum pyrolysis over magnesium. Part 1 - Pyrolysis of benzylic, other aryl/alkyl and aliphatic halides

Flash vacuum pyrolysis over a bed of freshly sublimed magnesium on glass wool results in efficient coupling of benzyl halides to give the corresponding bibenzyls. Where an ortho halogen substituent is present further dehalogenation gives some dihydroanthracene and anthracene. Efficient coupling is also observed for halomethylnaphthalenes and halodiphenylmethanes while chlorotriphenylmethane gives 4,4′-bis(diphenylmethyl)biphenyl. By using α,α′-dihalo-o-xylenes, benzocyclobutenes are obtained in good yield, while the isomeric α,α′-dihalo-p-xylenes give a range of high thermal stability polymers by polymerisation of the initially formed p-xylylenes. Other haloalkylbenzenes undergo largely dehydrohalogenation where this is possible, in some cases resulting in cyclisation. Deoxygenation is also observed with haloalkyl phenyl ketones to give phenylalkynes as well as other products. With simple alkyl halides there is efficient elimination of HCl or HBr to give alkenes. For aliphatic dihalides this also occurs to give dienes but there is also cyclisation to give cycloalkanes and dehalogenation with hydrogen atom transfer to give alkenes in some cases. For 5-bromopent-1-ene the products are those expected from a radical pathway but for 6-bromohex-1-ene they are clearly not. For 2,2-dichloropropane and 1,1-dichloropropane elimination of HCl occurs but for 1,1-dichlorobutane, -pentane and -hexane partial hydrolysis followed by elimination of HCl gives E, E-, E,Z- and Z,Z- isomers of the dialk-1-enyl ethers and fully assigned 13C NMR data are presented for these. With 6-chlorohex-1-yne and 7-chlorohept-1-yne there is cyclisation to give methylenecycloalkanes and -cycloalkynes. The behaviour of 1,2-dibromocyclohexane and 1,2-dichlorocyclooctane under these conditions is also examined. Various pieces of evidence are presented that suggest that these processes do not involve generation of free gas-phase radicals but rather surface-adsorbed organometallic species.

Ruthenium-phosphine complex and process for producing optically active 1-substituted-1,3-propanediols using the same as a catalyst

A ruthenium-phosphine complex is disclosed, represented by formula (I): where R1 -BINAP represents a tertiary phosphine represented by formula (II): STR1 wherein R1 represents a phenyl group which may be substituted with a lower alkyl group or a halogen atom at the p-position and/or m-position. A process for producing an optically active 1-substituted-1,3-propanediol is also disclosed, comprising hydrogenating a 3-substituted-3-oxopropanol or 3-substituted-3-oxopropanal in the presence of the ruthenium-phosphine complex of formula (I).

Process for producing optically active 1-substituted-1,3-propanediols using ruthenium-phosphine complex as a catalyst

A process for producing an optically active 1-substituted-1,3-propanediol is disclosed, comprising hydrogenating a 3-substituted-3-oxopropanol or 3-substituted-3-oxopropanal in the presence of a ruthenium-phosphine complex represented by formula (I): wherein R1 -BINAP represents an optically active tertiary phosphine represented by formula (II): STR1 wherein R1 represents a phenyl group which may be substituted with a lower alkyl group or a halogen atom at the p-position and/or m-position.