1008-73-7

Usage

Uses

Used in Pharmaceutical Industry:
Dihydro-4-phenylfuran-2(3H)-one is used as a key intermediate in organic synthesis for the production of pharmaceuticals. Its unique structure and properties make it a valuable building block in the development of new chemical entities with therapeutic applications.
Used in Fragrance and Flavor Industry:
dihydro-4-phenylfuran-2(3H)-one is utilized as a raw material in the fragrance and flavor industry due to its aromatic smell. Its distinctive scent profile contributes to the creation of various fragrances and flavorings for consumer products.
Used in Medicinal Chemistry Research:
Dihydro-4-phenylfuran-2(3H)-one is employed in medicinal chemistry research for its promising biological activities. Its potential as a pharmaceutical candidate is being explored for the development of new drugs and therapeutic agents.

InChI:InChI=1/C10H10O2/c11-10-6-9(7-12-10)8-4-2-1-3-5-8/h1-5,9H,6-7H2

Upstream product

• 96-09-3 styrene oxide 
• 64-17-5 ethanol 
• 996-82-7 sodium diethylmalonate 
• 105-53-3 diethyl malonate 
• 36122-35-7 2-phenylmaleic anhydride 
• 128372-48-5 4-Phenyltetrahydrofuran-2-ol 
• 78920-27-1 5-ethoxy-4,5-dihydro-4-phenylfuran-2(3H)-one 
• 1131-15-3 2-phenylsuccinic anhydride 
• 52784-31-3 3-Phenylcyclobutanone 
• 38330-80-2 monomethyl monopotassium malonate 
• 70-11-1 α-bromoacetophenone 
• 99512-42-2 methyl 5-oxo-3-phenylhexanoate 
• 369-57-3 benzenediazonium tetrafluoroborate 
• 72900-28-8 2-((Z)-4-(tetrahydro-2H-pyran-2-yloxy)but-2-enyloxy)-tetrahydro-2H-pyran 

Downstream Products

• 80775-84-4 3-(4-Fluoro-benzoyl)-4-phenyl-dihydro-furan-2-one 
• 80775-61-7 α-benzoyl-β-phenyl-γ-butyrolactone 
• 135211-20-0 (-)-(R,S)-4-Hydroxy-3-phenyl-N-(1-phenylethyl)butanamide 
• 135094-06-3 (-)-(S,S)-4-Hydroxy-3-phenyl-N-(1-phenylethyl)butanamide 
• 40951-19-7 sodium 4-hydroxy-3-phenylbutanoate 
• 128372-48-5 4-Phenyltetrahydrofuran-2-ol 
• 1145-92-2 (1SR,2SR)-phenyl(2-phenylcyclopropyl)ketone 
• 42509-29-5 4-chloro-1,3-diphenyl-1-butanone 
• 80775-62-8 4-chloro-1-(4-fluorophenyl)-3-phenyl-1-butanone 
• 42509-30-8 2-(3-chloro-2-phenylpropyl)-2-phenyl-1,3-dioxolane 
• 80775-66-2 2-<3-chloro-2-(4-fluorophenyl)propyl>-2-phenyl-1,3-dioxolane 
• 42509-32-0 4-[4-(4-Chloro-phenyl)-4-hydroxy-piperidin-1-yl]-1,3-diphenyl-butan-1-one 
• 42557-20-0 4-[4-(4-Chloro-phenyl)-4-hydroxy-piperidin-1-yl]-1-(4-fluoro-phenyl)-3-phenyl-butan-1-one 
• 80775-73-1 1-[1-(4-Oxo-2,4-diphenyl-butyl)-piperidin-4-yl]-1,3-dihydro-benzoimidazol-2-one 

Relevant academic research and scientific papers

An aerobic, organocatalytic, and chemoselective method for Baeyer-Villiger oxidation

(Chemical Equation Presented) Highly chemoselective Baeyer-Villiger oxidations can be performed in the presence of other reactive functionalities such as alcohols, olefins, and sulfides, which would undergo electrophilic oxidation under conventional conditions (see scheme). [DMRFlEt] +[ClO4]- (depicted blue) is a new class of flavin compound that catalyzes aerobic Baeyer-Villiger oxidations in the presence of Zn dust as the electron source.

Iridium-catalyzed enantioselective allylic alkylation of methyl 2-(4-nitrophenylsulfonyl)acetate and subsequent transformations

Highly enantioselective allylic alkylation reactions of methyl 2-(4-nitrophenylsulfonyl)acetate were carried out in the presence of an iridium catalytic system. The subsequent transformations of the products including reductive desulfonylation and modifie

Acetic Acid as a Highly Reactive and Easily Separable Catalyst for the Oxidative Cleavage of Tetrahydrofuran-2-methanols to γ-Lactones

[4-Iodo-3-(isopropylcarbamoyl)phenoxy]acetic acid was developed as a highly reactive and easily separable catalyst for the oxidative cleavage of tetrahydrofuran-2-methanols to γ-lactones in the presence of Oxone (2KHSO 5 ·KHSO 4 ·K 2 SO 4) as the co-oxidant. The reactivity of this new catalyst was considerably greater than that of our previously reported catalyst, 2-iodo-N-isopropylbenzamide. The new catalyst and product were easily separated by only liquid-liquid separation without chromatography. In addition, using a mixture of nitromethane and N, N-dimethylformamide as the solvent and heating enabled a low catalyst loading, a short reaction time, and high product yield. Oxidative cleavage using the new catalyst can be used as a practical and efficient method for synthesizing γ-lactones.

Asymmetric Baeyer-Villiger oxidation with Co(Salen) and H2O 2 in water: Striking supramolecular micelles effect on catalysis

A micellar environment enables catalytic, diastereoselective and enantioselective Baeyer-Villiger oxidation of cyclobutanones (ee up to 90%) with H2O2 as oxidant using Co(Salen) catalyst 1, while the same catalytic system is inactive in organic solvents. The Royal Society of Chemistry 2009.

Investigation of a New Type I Baeyer–Villiger Monooxygenase from Amycolatopsis thermoflava Revealed High Thermodynamic but Limited Kinetic Stability

Baeyer–Villiger monooxygenases (BVMOs) are remarkable biocatalysts, but, due to their low stability, their application in industry is hampered. Thus, there is a high demand to expand on the diversity and increase the stability of this class of enzyme. Sta

Design of peptide-containing: N 5-unmodified neutral flavins that catalyze aerobic oxygenations

Simulation of the monooxygenation function of flavoenzyme (Fl-Enz) has been long-studied with N5-modified cationic flavins (FlEt+), but never with N5-unmodified neutral flavins (Fl) despite the fact that Fl is genuinely equal to the active center of Fl-Enz. This is because of the greater lability of 4a-hydroperoxy adduct of Fl, FlOOH, compared to those of FlEt+, FlEtOOH, and Fl-Enz, FlOOH-Enz. In this study, Fl incorporated into a short peptide, flavopeptide (Fl-Pep), was designed by a rational top-down approach using a computational method, which could stabilize the corresponding 4a-hydroperoxy adduct (FlOOH-Pep) through intramolecular hydrogen bonds. We report catalytic chemoselective sulfoxidation as well as Baeyer-Villiger oxidation by means of Fl-Pep under light-shielding and aerobic conditions, which are the first Fl-Enz-mimetic aerobic oxygenation reactions catalyzed by Fl under non-enzymatic conditions.

Silyl peroxides as effective oxidants in the Baeyer-Villiger reaction with chloroaluminate(III) ionic liquids as catalysts

A new application of silyl peroxides as oxidants in the Baeyer-Villiger oxidation of cyclic ketones in chloroaluminate(III) ionic liquids is described. Among the silyl peroxides, the reactivity of two groups of peroxides was studied: bis(silyl) and t-butyl silyl peroxides possessing different structured substituents attached to the Si atom. It was shown that the acidic 1-hexyl-3-methylimidazolium chloroaluminate(III) ionic liquid (molar ratio of AlCl3 in ionic liquid: 0.67) present in the oxidation of cyclic ketones with bis(silyl) peroxides acts as the catalyst. In this variant of the reaction, the reactivities of bis(silyl) peroxides decrease in the following order: bis(trimethylsilyl) peroxide > bis(vinyldimethylsilyl) peroxide > bis(phenyldimethylsilyl) peroxide > bis(diphenylmethylsilyl) peroxide. A variety of cyclic ketones such as cyclobutanone, 3-substituted cyclobutanones, cyclopentanone, cyclohexanone, 2-methylcyclohexanone, 4-methylcyclohexanone, 2-adamantanone and norcamphor were oxidised to their corresponding lactones with high yields (49-100%). When t-butyl silyl peroxides and neutral chloroaluminate(III) ionic liquids (molar ratio of AlCl3 in ionic liquid: 0.5) were utilised in the Baeyer-Villiger oxidation, the studied ionic liquid acted as the reagent. Here, phenyldimethyl(t-butylperoxy)silane was the most efficient oxidant in the oxidation of cyclobutanone to γ- butyrolactone (70% yield). Other peroxides, including trimethyl(t-butylperoxy) silane, vinyldimethyl(t-butylperoxy)silane and diphenylmethyl-(t-butylperoxy) silane, were less reactive oxidants. Two variants of the Baeyer-Villiger reaction mechanism are postulated.

Dehydrogenative lactonization of diols in aqueous media catalyzed by a water-soluble iridium complex bearing a functional bipyridine ligand

A new catalytic system for the dehydrogenative lactonization of a variety of benzylic and aliphatic diols in aqueous media was developed. By using a water-soluble, dicationic iridium catalyst bearing 6,6′-dihydroxy-2, 2′-bipyridine as a functional ligand, highly atom economical and environmentally benign synthesis of various lactones was achieved in good to excellent yields. Recovery and reuse of the catalyst were also accomplished by a simple phase separation and the recovered catalyst maintained its high activity at least until the fifth run. Copyright

Asymmetric Baeyer-Villiger oxidation of prochiral cyclobutanones using a chiral cationic palladium(II) 2-(phosphinophenyl)pyridine complex as catalyst

Chiral cationic palladium(II) 2-(phosphinophenyl)pyridine (1a) complex was found to be an effective catalyst for asymmetric Baeyer-Villiger oxidation of prochiral cyclobutanones. For example, good and excellent enantioselectivities (80% and >99% ees) were

CATALYTIC REGIOSELECTIVE DEHYDROGENATION OF UNSYMMETRICAL α,ω-DIOLS USING RUTHENIUM COMPLEXES

Ruthenium complex catalyzed regioselective dehydrogenation of unsymmetrically substituted 1,4- and 1,5-diols in the presence of α,β-unsaturated ketone as a hydrogen acceptor and triethylamine gave β-substituted γ-lactones and γ-substituted δ-lactones as major products, respectively.