63295-11-4

Usage

Chemical class

Furanone

Derivative

Dihydro derivative of 5,5-bis(4-fluorophenyl)furan-2(3H)-one

Potential applications

Pharmaceutical and agricultural industries

Bioactive properties

Antioxidant, antibacterial, and antifungal
Possible use as a flavor and fragrance ingredient

Ongoing research

Further investigation into potential applications and properties.

Upstream product

• 6175-14-0 1,1-bis-(4-fluorophenyl)ethene 
• 14284-89-0 manganese(III) acetylacetonate 
• 64-19-7 acetic acid 
• 345-92-6 4,4'-Difluorobenzophenone 
• 75-05-8 acetonitrile 
• 462-06-6 fluorobenzene 
• 543-20-4 succinoyl dichloride 
• 108-24-7 acetic anhydride 

Downstream Products

• 134179-57-0 7-fluoro-4-(3-fluorophenyl)naphthalen-1-ol 
• 149530-23-4 5,5-Bis-(4-fluorphenyl)-2-oxo-4,5-dihydro-3H-furan-3-carbonsaeure 

Relevant academic research and scientific papers

Electroreductive coupling of aromatic ketones, aldehydes, and aldimines with α,β-unsaturated esters: Synthesis of 5-aryl substituted γ-butyrolactones and lactams

The electroreductive intermolecular coupling of aromatic ketones and aldehydes with α,β-unsaturated esters in the presence of TMSCl gave the adducts as γ-trimethylsiloxy esters. The detrimethylsilylation of the adducts with TBAF afforded 5-aryl substituted γ-butyrolactones. The electroreductive coupling of N-(4-methoxyphenyl)-1-arylmethaneimines with methyl acrylate in the presence of TMSCl gave the adducts as methyl 4-aryl-4-((4-methoxyphenyl)amino)butanoates. The adducts were transformed to 5-aryl-γ-butyrolactams by cyclization with NaH and subsequent oxidation with CAN. (±)-Norcotinine was prepared from nicotinaldehyde by this method. The electroreductive coupling of aromatic ketones and aldimines with acrylonitrile in the presence of TMSCl gave 4-aryl-4-(trimethylsiloxy)butanenitriles and 4-aryl-4-((4-methoxyphenyl)amino)butanenitriles, respectively.

Copper-Catalyzed Formal [2+2+1] Heteroannulation of Alkenes, Alkylnitriles, and Water: Method Development and Application to a Total Synthesis of (±)-Sacidumlignan D

A copper-catalyzed three-component reaction of alkenes, alkylnitriles, and water affords γ-butyrolactones in good yields. The domino process involves an unprecedented hydroxy-cyanoalkylation of alkenes and subsequent lactonization with the creation of three chemical bonds and a quaternary carbon center. The synthetic potential of this novel [2+2+1] heteroannulation reaction was illustrated by a concise total synthesis of (±)-sacidumlignan D.

Oxygenation of Tetrahydrofurans with Combined Use of Molecular Oxygen and α-Diketone Catalyzed by Cobalt(III) Complex

In the presence of catalytic amount of cobalt(III) complex such as tris(acetylacetonato)cobalt(III), tetrahydrofurans are oxygenated into the corresponding γ-butyrolactones under mild conditions on treatment with an atmospheric pressure of molecular oxygen and α-diketones having hydrogen atom next to the carbonyl carbon.

Formation of 1,2-Dioxanes by the Use of Tris(2,4-pentanedionato)manganese(III) or Manganese(III) Acetate

The reactions of 1,1-diphenylethene, 1,1-bis(4-chlorophenyl)ethene, 1,1-bis(4-methoxyphenyl)ethene, 1,1-bis(4-methylphenyl)ethene, 1,1-bis(4-fluorophenyl)ethene, styrene, 1-octene, cyclohexene, and cyclooctene with tris(2,4-pentanedionato)manganese(III) () in acetic acid at room temperature give 4-acetyl-3-methyl-1,2-dioxan-3-ol in 8-92percent yields, together with 3-acetyl-4-hydroxy-3-hexene-2,5-dione.The similar reactions of 1,1-diphenylethene with 2,4-pentanedione, 3-methyl-2,4-pentanedione, 3-ethyl-2,4-pentanedione, 1-phenyl-1,3-butanedione, acetoacetanilide, and 1,3-cyclohexanedione in the presence of manganese(III) acetate also give the corresponding cyclic peroxide in good to moderate yields.The mechanisms of manganese(III)-induced 1,2-dioxane ring formation and concomitant radical side reaction are discussed.