143392-24-9

Usage

Structure

2(5H)-furanone with a 4-(2-methylphenyl) group

Aromatic fragrance

sweet, woody, and fruity

Usage

as a synthetic flavor and fragrance agent to impart a sweet, caramel-like aroma to various products

Potential natural antioxidant

with anti-inflammatory and antimicrobial properties

Interest for applications

in the pharmaceutical and cosmetic industries

Use in synthesis

of pharmaceuticals and fine chemicals due to its unique chemical properties.

Upstream product

• 615-37-2 ortho-methylphenyl iodide 
• 57061-30-0 4-Phenylsulfanylfuran-2(5H)-one 
• 201230-82-2 carbon monoxide 
• 766-47-2 1-ethynyl-2-methylbenzene 
• 541-57-1 4-hydroxy-2(5H)-furanone 
• 16419-60-6 2-Methylphenylboronic acid 
• 189078-68-0 tert-butyl buta-2,3-dienoate 
• 139446-54-1 3-(o-tolyl)-3-butenoic acid 
• 145439-09-4 4-(tributylstannyl)-2,5-dihydrofuran-2-one 

Downstream Products

• 80866-25-7 3-(o-tolyl)furan 

Relevant academic research and scientific papers

Oxidative Cyclization of β,γ-Unsaturated Carboxylic Acids Using Hypervalent Iodine Reagents: An Efficient Synthesis of 4-Substituted Furan-2-ones

The oxidative cyclization of β-substituted β,γ-unsaturated carboxylic acids using a hypervalent iodine reagent to provide 4-substituted furan-2-one products, is reported. In this cyclization, the use of a highly electrophilic PhI(OTf) 2, which is in situ prepared from PhI(OAc) 2 and Me 3 SiOTf, is crucial. Depending on the substitution pattern at the α-position of the substrates, furan-2(5 H)-ones or furan-2(3 H)-ones are produced. Thus, the present method offers a useful tool for accessing various types of 4-substituted furan-2-ones that are important structural motifs in the field of organic chemistry and medicinal chemistry.

Gold-catalyzed cascade oxidative cyclization and arylation of allenoates

An AuI/AuIII catalytic system was found to be effective for the cascade oxidative arylation and cyclization of allenoates with arylboronic acids to give the corresponding cyclic adducts in moderate yields. This reaction system constitutes a new method for the synthesis of β-aryl-γ-butenolides under mild conditions. Based on the previous mechanistic studies, a proposed AuI/AuIII redox catalytic cycle has been outlined. An AuI/AuIII catalytic system was found to be effective for the cascade oxidative arylation and cyclization of allenoates with various arylboronic acids to give the corresponding cyclic adducts in moderate yields. This reaction system enabled the synthesis β-aryl-γ-butenolides under mild conditions. Based on previous mechanistic studies, an AuI/AuIII redox catalytic cycle has been outlined. Copyright

Rapid access to 4-substituted-pyrones and 2(5H)-furanones via a palladium-catalyzed C-OH bond activation

An efficient palladium-catalyzed cross-coupling reaction of 4-hydroxy-pyrone or 4-hydroxy-2(5H)-furanone with arylboronic acid is described, which affords the 4-substituted-pyrones and 2(5H)-furanones in good yields. This transformation proceeds through a C-OH bond activation under mild conditions.

Preparation and reactions of 3,4-bisstannyl-2(5H)furanones

Bistributylstannyl-2(5H)-furanone 4a has been prepared from 3-(tetrahydropyran-2-yl)oxy but-2-ynoate and shown to exhibit good selectivity in its Stille reactions with a range of halogenated compounds, leading to 4-substituted-3-stannyl-2(5H)-furanones, in generally moderate yield. Under certain reaction conditions, doubly substituted products were also isolated from the reactions. The 3,4-bistrimethylstannyl furanone, 4b, corresponding to 4a was prepared, but decomposed during all attempts to execute Stille reactions upon it.

An expedient palladium-mediated route to 3-arylfurans

A facile route to 3-arylfurans has been developed by employing the Heck reaction between 2,5-dihydro-2,5-dimethoxyfuran and aryl iodides as the key step.

Preparation and palladium-catalysed cross-coupling reactions of 3-and 4-tributylstannylfuran-2(5H)-ones

Stannylfuranones 1 and 2 were prepared by ipso radical desulfurative stannylation of phenylsulfanylfuranones 3 and 16. Compounds 1 and 2 underwent Stille coupling reactions with aryl iodides to give 3- and 4-arylfuran-2(5H)-ones.

Reductive Carbonylation of Acetylenes under Water-Gas Shift Reaction Conditions. Synthesis of Furan-2(5H)-ones from Terminal and Non-substituted Acetylenes

Under water-gas reaction conditions terminal and non-substituted acetylenes are selectively converted into furan-2(5H)-ones by catalysis with a rhodium carbonyl cluster.

Preparation and reactions of 3-and 4-tributylstannyl-2-(5H)-furanones: Preparation of aryl furanones

3- and 4-trialkylstannylfuranones (2) and (3) have been prepared by an interesting desulphurative stannylation reaction; 3- and 4-substituted 2-(5H)-Furanones (12) and (13) may be prepared via palladium-catalysed cross coupling of (2) and (3) with aryl iodides.