415944-56-8

Basic information

• Product Name: 2-Buten-1-one, 4,4,4-trifluoro-3-hydroxy-1-(4-methoxyphenyl)-
• CAS NO: 415944-56-8
• Molecular Formula: C11H9F3O3
• Molecular Weight: 246.186
• Mol File: 415944-56-8.mol

Chemical Properties

• CAS DataBase Reference: 2-Buten-1-one, 4,4,4-trifluoro-3-hydroxy-1-(4-methoxyphenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Buten-1-one, 4,4,4-trifluoro-3-hydroxy-1-(4-methoxyphenyl)-(415944-56-8)
• EPA Substance Registry System: 2-Buten-1-one, 4,4,4-trifluoro-3-hydroxy-1-(4-methoxyphenyl)-(415944-56-8)

Safety Data

• Hazardous Substances Data: 415944-56-8(Hazardous Substances Data)

Upstream product

• 383-63-1 ethyl trifluoroacetate, 
• 100-06-1 1-(4-methoxyphenyl)ethanone 

Downstream Products

• 60755-22-8 1-(4-methoxyphenyl)-4-phenyl-1,4-butanedione 
• 121-98-2 methyl 4-methoxybenzoate 
• 32766-61-3 4-methoxyphenylglyoxylate methyl ester 
• 73744-44-2 2-fluoro-4'-methoxyacetophenone 

Relevant articles and documents

Palladium-Catalyzed Benzodifluoroalkylation of Alkynes: A Route to Fluorine-Containing 1,1-Diarylethylenes

A palladium(0)-catalyzed three-component reaction of 2-iodo-2,2-difluoroacetophenones, alkynes and arylboronic acids is introduced for the synthesis of 1-benzoyldifluoromethyl-2,2-diphenylethylenes in good yields and with excellent stereoselectivity. The

Nickel-Catalyzed Aminofluoroalkylation of Alkenes: Access to Difluoroalkylated N-Containing Heterocyclic Compounds

A nickel-catalyzed aminofluoroalkylative cyclization of unactive alkenes with iododifluoromethyl ketones was developed to construct versatile difluoroalkylated Nitrogen-containing heterocycles including aziridines, pyrrolidines and piperidines in moderate to high yields. This method features a broad substrate scope and has been demonstrated on gram scale.

Copper-Catalyzed Three-Component Reactions of 2-Iodo-2,2-difluoroacetophenones, Alkynes, and Trimethylsilyl Cyanide

A Cu(I)-catalyzed three-component reaction of 2-iodo-2,2-difluoroacetophenones, alkynes, and TMSCN is described. The reaction provided a facile method for the synthesis of difluoroacyl-substituted nitriles, which might be served as potentially useful fluo

Nickel-Catalyzed Coupling Reaction of α-Bromo-α-fluoroketones with Arylboronic Acids toward the Synthesis of α-Fluoroketones

A nickel-catalyzed coupling reaction of α-bromo-α-fluoroketones with arylboronic acids was reported, which provides an efficient pathway to access 2-fluoro-1,2-diarylethanones in high yields. We also disclosed the synthesis of the monofluorination agents

Detrifluoroacetylation Reaction of Trifluoromethyl-β-diketones: Facile Method for the Synthesis of Succinimide Derivatives and 1,4-Diketones

Currently, a great deal of research efforts are focused on C–C bond activation for development of novel synthetic methodology. In this paper, a detrifluoroacetylation of trifluoromethyl-β-diketones is described, which allows for the synthesis of succinimides and 1,4-diketones through cascade Michael addition/retro-Claisen reaction and nucleophilic substitution/retro-Claisen reaction. The readily available trifluoromethyl-β-diketones, wide substrate scope, and mild conditions make this method very practical.

Synthesis of α,α-difluorobenzoyl oxygen heterocycles via the radical reaction of 2-iodo-2,2-difluoroacetophenones with unsaturated acids or unsaturated alcohols

A convenient and facile method for the direct synthesis of α,α-difluorobenzoyl lactones or cyclic ethers via the radical cyclization reaction of 2-iodo-2,2-difluoroacetophenone with unsaturated acids or alcohols was reported.

Palladium-catalyzed direct mono-α-arylation of α-fluoroketones with aryl halides or phenyl triflate

A palladium catalyzed Negishi-type α-arylation of α-fluoroketones with electron-rich and electron-deficient aryl halides or phenyl triflate has been developed. This direct mono-α-arylation method generate a variety of ternary α-aryl-α-monofluoroketones easily in good to excellent yields using XPhos as ligand and Cs2CO3as mild base.

Synthesis of difluoroalkyl-γ-butyrolactones from iododifluoromethyl ketones and 4-pentenoic acids

A convenient and efficient approach for difluoroalkyl-containing γ-butyrolactones via the radical addition reaction of iododifluoromethyl ketones with 4-pentenoic acids initiated by AIBN in CH3CN at 60 °C was reported. Various difluoroalkyl-containing δ-valerolactones were also synthesized under this reaction conditions.

Highly tunable fluorinated trispyrazolylborates [HB(3-CF3-5-{4-RPh}pz)3]- (R = NO2, CF3, Cl, F, H, OMe and NMe2) and their copper(i) complexes

The ethene and carbon monoxide adducts of copper(i) with seven trispyrazolylborate ligands ([HB(3-CF3-5-{4-RPh}pz)3]-; R = NO2 (4a), CF3 (4b), Cl (4c), F (4d), H (4e), OMe (4f) and NMe2 (4g)) were synthesized and characterized. The ligands were synthesized from their corresponding pyrazoles and sodium tetrahydridoborate and were obtained as solvent adducts of their sodium salts after workup. When the pyrazole with the most electron-withdrawing substituent (R = NO2) is used the asymmetric ligand [HB(3-CF3-5-{4-NO2Ph}pz)2(3-{4-NO2Ph}-5-CF3pz)]- (4a′) is formed as the major product. Copper(i) complexes with ethene or CO as a co-ligand were prepared in good yields and were structurally characterized using 1H NMR, 13C NMR and infrared spectroscopy. Single crystal X-ray crystallography analyses revealed the structures of Na4a′, Na4b, four copper ethene complexes and four copper carbonyl complexes. The structures of the copper(i) complexes show CuI ions in pseudo-tetrahedral coordination environments consisting of three nitrogen atoms of the trispyrazolylborate ligand and the carbonyl or η2-coordinated ethene ligands, with nearly identical coordination environments around the CuI ion. The compound [Na(4a′)(H2O)]n crystallizes as one-dimensional chains with intermolecular Na...O2N interactions. The sodium ions were found in severely distorted octahedral geometries with three nitrogen atoms from the trispyrazolylborate ligand, one aqua ligand and two oxygen atoms from the nitro group of an adjacent molecule. The compound [Na2(4b)2(μ-H2O)2] crystallizes as a centrosymmetric water-bridged dimer: two five-coordinate square-pyramidal sodium ions each are coordinated facially by three nitrogen atoms from a trispyrazolylborate ligand and two bridging water ligands. Below the base of the pyramidal structure one intermolecular and two intramolecular Na...F short contacts are present. The 1H and 13C NMR spectra of the copper-ethene complexes show signals for the ethene ligands in the range of 4.84-4.96 ppm and 84.9-86.8 ppm respectively. The infrared spectra of the carbonyl complexes show CO stretching frequencies in the range of 2096-2120 cm-1. Both the NMR signals for the ethene ligands and infrared signals for the carbonyl ligands were found to show good correlations with the Hammett σp parameters of the substituents on the phenyl rings of the ligands.

Highly enantioselective construction of 3-hydroxy oxindoles through a decarboxylative aldol addition of trifluoromethyl α-fluorinated gem-diols to n-benzyl isatins

An organocatalytic asymmetric direct aldol addition reaction that involves cleavage of a carbon-carbon bond through the release of trifluoroacetate was developed. The protocol is wide in scope, generating the desired oxindoles of biological interest in nearly quantitative yields (up to 99 %) with excellent enantioselectivities (up to 98 % ee) and diastereoselectivities (up to 99:1 d.r.). Copyright