5739-38-8

Usage

Uses

Used in Pharmaceutical Synthesis:
1-(4-methoxyphenyl)-3-phenyl-propan-1-one is used as a key intermediate in the pharmaceutical industry for the synthesis of various pharmaceuticals and organic compounds. Its role in the production process is crucial due to its ability to form the backbone of these compounds.
Used in the Production of Amphetamines:
In the chemical industry, 1-(4-methoxyphenyl)-3-phenyl-propan-1-one is used as a precursor in the production of amphetamines and other psychoactive substances. Its chemical structure allows for further modification and synthesis into these compounds.
Used in Research and Development:
1-(4-methoxyphenyl)-3-phenyl-propan-1-one is also utilized in the research and development sector for studying the properties and potential applications of ketone functional group compounds. Its unique structure makes it an interesting subject for scientific inquiry and innovation.

InChI:InChI=1/C16H16O2/c1-18-15-10-8-14(9-11-15)16(17)12-7-13-5-3-2-4-6-13/h2-6,8-11H,7,12H2,1H3

Upstream product

• 100-66-3 methoxybenzene 
• 645-45-4 hydrocinnamic acid chloride 
• 501-52-0 3-Phenylpropionic acid 
• 36941-00-1 1-(4-hydroxyphenyl)-3-phenylpropan-1-one 
• 77-78-1 dimethyl sulfate 
• 959-23-9 4'-methoxychalcone 
• 100-06-1 1-(4-methoxyphenyl)ethanone 
• 100-51-6 benzyl alcohol 
• 25150-08-7 1-[1-(benzyloxy)ethenyl]-4-methoxybenzene 
• 100-42-5 styrene 
• 65842-37-7 (4-methoxyphenyl)(phenylseleno)methanone 
• 3277-89-2 phenethylmagnesium bromide 
• 16090-04-3 p-methoxybenzoic acid Li-salt 
• 31663-21-5 2-Benzenesulfonyl-1-(4-methoxy-phenyl)-3-phenyl-propan-1-one 

Downstream Products

• 24788-17-8 1-(4-methoxy-phenyl)-3-phenylpropan-1-ol 
• 106511-71-1 2-Bromo-1-(4'-methoxyphenyl)-3-phenyl-1-propanone 
• 122075-95-0 β-phenyl-4-methoxypropiophenone-α,α-d₂ 
• 36941-00-1 1-(4-hydroxyphenyl)-3-phenylpropan-1-one 
• 719310-84-6 3-phenyl-1-(4-triisopropylsilanyloxy-phenyl)-propan-1-one 
• 719311-06-5 2-bromo-3-phenyl-1-(4-triisopropylsilanyloxy-phenyl)-propan-1-one 
• 719311-30-5 2-(2,5-dihydroxy-phenylsulfanyl)-3-phenyl-1-(4-triisopropylsilanyloxy-phenyl)-propan-1-one 
• 106511-75-5 5-Benzyl-4-(4-methoxy-phenyl)-thiazole-2-thiol 
• 106511-73-3 5-benzyl-4-(4-methoxyphenyl)thiazol-2-amine 
• 106511-76-6 5-Benzyl-4-(4-methoxy-phenyl)-2-methylsulfanyl-thiazole 
• 106511-74-4 N-[5-Benzyl-4-(4-methoxy-phenyl)-thiazol-2-yl]-acetamide 
• 86355-51-3 1,1-bis(p-hydroxyphenyl)-3-phenylpropane 
• 86355-50-2 1-(p-hydroxyphenyl)-1-(p-methoxyphenyl)-3-phenylpropane 
• 86476-31-5 Acetic acid 4-[1-(4-methoxy-phenyl)-3-phenyl-propyl]-phenyl ester 

Relevant academic research and scientific papers

Intramolecular Quenching of Carbonyl Triplets by β-Phenyl Rings

The presence of a phenyl ring in a position β to the carbonyl of a phenyl alkyl ketone results in greatly reduced ketone triplet lifetimes.For example, in deaerated benzene solutions, triplet lifetimes were 2700 and 0.89 ns for propiophenone (P) and β-phe

Nickel-Catalyzed Selective Synthesis of α-Alkylated Ketones via Dehydrogenative Cross-Coupling of Primary and Secondary Alcohols

Herein, we describe an isolable, air-stable, homogeneous, nickel catalyst that performs dehydrogenative cross-coupling reaction between secondary and primary alcohols to result α-alkylated ketone products selectively. The sequence of steps involve in this one-pot reaction is dehydrogenation of both alcohols, condensation between the ketone and the aldehyde, and hydrogenation of the in situ-generated α,β-unsaturated ketone. Preliminary mechanistic investigation hints a radical mechanism following borrowing hydrogen reaction. (Figure presented.).

Nickel-catalyzed α-alkylation of ketones with benzyl alcohols

We reported an efficient method for α-alkylation of ketones with benzyl alcohols using the pyridine-bridged pincer-type N-heterocyclic carbenes nickel complexes as catalysts. A wide range of ketones and benzyl alcohols were efficiently converted into various alkylated products in moderate to high yields. In addition, these nickel complexes were also successfully applied for the synthesis of a wide range of quinoline derivatives.

BTP-Rh@g-C3N4 as an efficient recyclable catalyst for dehydrogenation and borrowing hydrogen reactions

Highly active catalysts play an important role in modern catalysis. A novel and efficient ligand benzotriazole-pyrimidine (BTP) and the corresponding rhodium composite on C3N4 were successfully synthesized. The resulting rhodium composite was fully characterized by scanning electron microscopy (SEM), transmission electron microscopy (TEM), x-ray diffraction (XRD), thermogravimetric analysis (TGA), and x-ray photoelectron spectroscopy (XPS). The obtained composite exhibited good catalytic activity and good recovery performance in the synthesis of quinoxaline from 2-aminobenzyl alcohol and benzonitrile, and more than 20 quinoxalines were obtained in good yields. Additionally, it also showed that rhodium composite could achieved good catalytic performance in the synthesis of functionalized ketone through borrowing hydrogen strategy.

Highly Selective Hydrogenation of C═C Bonds Catalyzed by a Rhodium Hydride

Under mild conditions (room temperature, 80 psi of H2) Cp*Rh(2-(2-pyridyl)phenyl)H catalyzes the selective hydrogenation of the C═C bond in α,β-unsaturated carbonyl compounds, including natural product precursors with bulky substituents in the β position and substrates possessing an array of additional functional groups. It also catalyzes the hydrogenation of many isolated double bonds. Mechanistic studies reveal that no radical intermediates are involved, and the catalyst appears to be homogeneous, thereby affording important complementarity to existing protocols for similar hydrogenation processes.

Selective catalytic synthesis of α-alkylated ketones and β-disubstituted ketones via acceptorless dehydrogenative cross-coupling of alcohols

Herein, a phosphine-free pincer ruthenium(III) catalyzed β-alkylation of secondary alcohols with primary alcohols to α-alkylated ketones and two different secondary alcohols to β-branched ketones are reported. Notably, this transformation is environmentally benign and atom efficient with H2O and H2 gas as the only byproducts. The protocol is extended to gram-scale reaction and for functionalization of complex vitamin E and cholesterol derivatives.

The: In situ fabrication of ZIF-67 on titania-coated magnetic nanoparticles: A new platform for the immobilization of Pd(ii) with enhanced catalytic activity for organic transformations

Considering the outstanding characteristics of metal organic frameworks (MOFs) and magnetic nanoparticles, herein we report a facile approach for the synthesis of a magnetic zeolitic-imidazolate-framework-supported palladium(ii) catalyst. In brief, zeolitic imidazolate framework-67 (ZIF-67) was successfully incorporated onto the surface of titania-coated magnetic nanoparticles using ethane-1,2-diamine as a linker, and then Pd(ii) was immobilized onto this. The resulting Pd@ZIF-67-Fe3O4-TiO2 catalyst possesses a high surface area (205 m2 g-1), a large pore volume (0.10 cm3 g-1), good magnetic responsivity (10.71 emu g-1), and high stability. A comparative analysis of Pd@ZIF-67-Fe3O4-TiO2 and Pd@Fe3O4-TiO2 catalysts for the oxidation, reduction, and oxidative deprotection of oximes was done to investigate the effects of ZIF-67 on the catalytic performance of Pd species. Substantial differences in activity and stability were observed in the presence of ZIF-67, suggesting that ZIF-67 plays an important role in enhancing the activity of Pd(ii). This superior catalytic activity and stability arises due to a synergistic effect between well-dispersed palladium species and highly porous ZIF-67, which was confirmed via XPS analysis. Moreover, the catalyst retains its structure, chemical environment, and good magnetic response even after five catalytic runs, as confirmed via FTIR, XRD, XPS, and VSM studies of reused catalyst samples.

A Proton-Responsive Pyridyl(benzamide)-Functionalized NHC Ligand on Ir Complex for Alkylation of Ketones and Secondary Alcohols

A Cp*Ir(III) complex (1) of a newly designed ligand L1 featuring a proton-responsive pyridyl(benzamide) appended on N-heterocyclic carbene (NHC) has been synthesized. The molecular structure of 1 reveals a dearomatized form of the ligand. The protonation of 1 with HBF4 in tetrahydrofuran gives the corresponding aromatized complex [Cp*Ir(L1H)Cl]BF4 (2). Both compounds are characterized spectroscopically and by X-ray crystallography. The protonation of 1 with acid is examined by 1H NMR and UV-vis spectra. The proton-responsive character of 1 is exploited for catalyzing α-alkylation of ketones and β-alkylation of secondary alcohols using primary alcohols as alkylating agents through hydrogen-borrowing methodology. Compound 1 is an effective catalyst for these reactions and exhibits a superior activity in comparison to a structurally similar iridium complex [Cp*Ir(L2)Cl]PF6 (3) lacking a proton-responsive pendant amide moiety. The catalytic alkylation is characterized by a wide substrate scope, low catalyst and base loadings, and a short reaction time. The catalytic efficacy of 1 is also demonstrated for the syntheses of quinoline and lactone derivatives via acceptorless dehydrogenation, and selective alkylation of two steroids, pregnenolone and testosterone. Detailed mechanistic investigations and DFT calculations substantiate the role of the proton-responsive ligand in the hydrogen-borrowing process.

Unveiling the catalytic nature of palladium-N-heterocyclic carbene catalysts in the α-alkylation of ketones with primary alcohols

We report herein the synthesis of four new Pd-PEPPSI complexes with backbone-modified N-heterocyclic carbene (NHC) ligands and their application as catalysts in the α-alkylation of ketones with primary alcohols using a borrowing hydrogen process and tandem Suzuki-Miyaura coupling/α-alkylation reactions. Among the synthesized Pd-PEPPSI complexes, complex2chaving 4-methoxyphenyl groups at the 4,5-positions and 4-methoxybenzyl substituents on the N-atoms of imidazole exhibited the highest catalytic activity in the α-alkylation of ketones with primary alcohols (18 examples) with yields reaching up to 95%. Additionally, complex2cwas demonstrated to be an effective catalyst for the tandem Suzuki-Miyaura-coupling/α-alkylation of ketones to give biaryl ketones with high yields. The heterogeneous nature of the present catalytic system was verified by mercury poisoning and hot filtration experiments. Moreover, the formation of NHC-stabilized Pd(0) nanoparticles during the α-alkylation reactions was identified by advanced analytical techniques.

Designed pincer ligand supported Co(ii)-based catalysts for dehydrogenative activation of alcohols: Studies onN-alkylation of amines, α-alkylation of ketones and synthesis of quinolines

Base-metal catalystsCo1,Co2andCo3were synthesized from designed pincer ligandsL1,L2andL3having NNN donor atoms respectively.Co1,Co2andCo3were characterized by IR, UV-Vis. and ESI-MS spectroscopic studies. Single crystal X-ray diffraction studies were investigated to authenticate the molecular structures ofCo1andCo3. CatalystsCo1,Co2andCo3were utilized to study the dehydrogenative activation of alcohols forN-alkylation of amines, α-alkylation of ketones and synthesis of quinolines. Under optimized reaction conditions, a broad range of substrates including alcohols, anilines and ketones were exploited. A series of control experiments forN-alkylation of amines, α-alkylation of ketones and synthesis of quinolines were examined to understand the reaction pathway. ESI-MS spectral studies were investigated to characterize cobalt-alkoxide and cobalt-hydride intermediates. Reduction of styrene by evolved hydrogen gas during the reaction was investigated to authenticate the dehydrogenative nature of the catalysts. Probable reaction pathways were proposed forN-alkylation of amines, α-alkylation of ketones and synthesis of quinolines on the basis of control experiments and detection of reaction intermediates.