76435-47-7

Upstream product

• 77092-12-7 6-phenyl-2,2-dimethyl-1,3-dioxin-4-one 
• 2579-22-8 Phenylpropargyl aldehyde 
• 614-27-7 methyl 3-oxo-3-phenylpropionate 
• 144765-06-0 (3R,4R)-3,4-Difluoro-4-phenyl-1,5-dioxa-spiro[5.5]undecan-2-one 
• 77092-27-4 4-oxo-6-phenyl-4H-1,3-dioxine-2-spirocyclohexane 
• 98-86-2 acetophenone 
• 67-56-1 methanol 
• 144765-10-6 3-Fluoro-4-phenyl-1,5-dioxa-spiro[5.5]undec-3-en-2-one 

Downstream Products

• 1177429-19-4 C₁₈H₁₆FNO₅ 
• 1260108-92-6 ditert-butyl (R)-1-(2-fluoro-1-methoxy-1,3-dioxo-3-phenylpropan-2-yl)hydrazine-1,2-dicarboxylate 
• 106791-94-0 2-amino-5-fluoro-6-phenylpyrimidin-4(3H)-one 
• 80171-22-8 4-fluoro-5-hydroxy-1-methyl-phenylpyrazole 

Relevant academic research and scientific papers

Synthesis of monofluorooxazoles with quaternary C-F centers through photoredox-catalyzed radical addition of methylene-2-oxazolines

A novel photoredox-catalyzed radical addition of methylene-2-oxazolines has been developed under visible light irradiation to synthesize monofluorooxazoles with a quaternary carbon center using 2-bromo-2-fluoro-3-oxo-3-phenylpropionates as radical source. This method with a simple protocol, scalability and high yield offers a facile path to get diverse monofluorinated oxazoles with quaternary C-F centers, which are a class of highly valuable motifs and synthons.

Transition metal-free functionalized hydration of alkynes: One-pot synthesis of fluorinated β-keto-imidates using Selectfluor

A transition metal-free, four-component one-pot synthesis of polyfunctionalized fluorinated β-keto-imidates via the functionalized hydration of alkynes has been described. The intermediate 1,3-ketoamino moiety was obtained from easily accessible arylpropioladehyde and arlyhydroxylamine and was treated with Selectfluor delivering fluorinated β-keto-imidates. A wide variety of functional groups are tolerated under mild reaction conditions and the product applicability is highlighted.

Iridium-Catalyzed Asymmetric Hydrogenation of Tetrasubstituted α-Fluoro-β-enamino Esters: Efficient Access to Chiral α-Fluoro-β-amino Esters with Two Adjacent Tertiary Stereocenters

An iridium-catalyzed highly efficient asymmetric hydrogenation of challenging tetrasubstituted α-fluoro-β-enamino esters was successfully developed using bisphosphine-thiourea (ZhaoPhos) as the ligand, which prepared a series of chiral α-fluoro-β-amino esters containing two adjacent tertiary stereocenters with high yields and excellent diastereoselectivities/enantioselectivities (73%-99% yields, >25:1 dr, 91%>99% ee, and turnover number (TON) values up to 8600), and no defluorinate byproduct was detected.

Organocatalytic Biomimetic Decarboxylative Aldol Reaction of Fluorinated β-Keto Acids with Unprotected Isatins

A facile asymmetric synthesis of fluorinated 3-hydroxyoxindoles through the biomimetic decarboxylative aldol reaction of fluorinated β-keto acids with unprotected isatins catalyzed by quinine-derived urea catalyst has been achieved. One of the features of this work is that the easily available α, α-difluoro/α-monofluoro-β-keto acids have been first applied in the enantioselective synthesis of fluorinated compounds as the masked fluoroenolates. Furthermore, the utility of this method was demonstrated by its ability to access a series of difluorinated 3-hydroxyoxindoles with up to 95% ee and monofluorinated 3-hydroxyoxindoles with up to 90 : 10 d.r. and 94% ee. (Figure presented.).

HTS followed by NMR based counterscreening. Discovery and optimization of pyrimidones as reversible and competitive inhibitors of xanthine oxidase

The identification of novel, non-purine based inhibitors of xanthine oxidase is described. After a high-throughput screening campaign, an NMR based counterscreen was used to distinguish actives, which interact with XO in a reversible manner, from assay artefacts. This approach identified pyrimidone 1 as a reversible and competitive inhibitor with good lead-like properties. A hit to lead campaign gave compound 41, a nanomolar inhibitor of hXO with efficacy in the hyperuricemic rat model after oral dosing.

Synthesis of 5-fluoro-1,3-dioxin-4-ones: Novel alternatives to α-fluorinated acyl ketenes

Fluorination of 5,6-unsubstituted 1,3-dioxin-4-ones and their 6-substituted derivatives by molecular fluorine followed by treatment with an appropriate organic base affords the title compounds, which can be converted either into heterocyclic compounds or into acylacetic acid derivatives having a fluorine atom.

FACILE SYNTHESIS OF α-FLUORO-β-KETOESTERS FROM POLYFLUOROALKENES

Alkyl 2-chloro-1,2,2-trifluoroethyl ketones and aryl 1,2,2,2-tetrafluoroethyl ketones were respectively prepared by the Friedel-Crafts acylation of trifluoroethene and by the Grignard arylation of N,N-diethyl-1,2,2,2-tetrafluoropropionamide, a hydrolyzed product of hexafluoropropene-diethylamine adduct.These alkyl and aryl polyfluoroalkyl ketones were subjected to base-induced dehydrohalogenation, and resulting trifluorovinyl ketones were hydrolyzed in situ affording α-fluoro-β-ketoesters in good yields.