126918-16-9

Usage

Uses

Used in Pharmaceutical Industry:
1-Propanone, 1-(2,4-difluorophenyl)-2-hydroxy-, (2R)is used as a key intermediate in the synthesis of chiral pharmaceuticals for the development of enantiomerically pure drugs. Its unique stereochemistry and functional groups enable the creation of complex molecular structures with specific biological activities, contributing to the advancement of novel therapeutic agents.
Used in Chemical Synthesis:
1-Propanone, 1-(2,4-difluorophenyl)-2-hydroxy-, (2R)is used as a versatile reagent in the production of epoxy alcohol compounds. Its ability to form epoxy alcohols through chemical reactions makes it a valuable building block in the synthesis of specialty chemicals, including agrochemicals, fragrances, and other fine chemicals, where stereoselectivity and functional group compatibility are crucial for the desired product properties.

Upstream product

• 126918-15-8 (S)-2-(p-toluenesulfonyloxy)-2',4'-difluoropropiophenone 
• 127001-03-0 (2R)-2',4'-Difluoro-2-(3,4,5,6-tetrahydro-2H-pyran-2-yloxy)propiophenone 
• 161457-74-5 (R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-(2,4-difluoro-phenyl)-propan-1-one 
• 148505-34-4 Acetic acid 2-(2,4-difluoro-phenyl)-1-methyl-2-oxo-ethyl ester 
• 85068-30-0 2',4'-difluoropropiophenone 
• 1550-35-2 2,4-difluorobenzaldehyde 
• 75-07-0 acetaldehyde 
• 126918-14-7 (2S)-2',4'-Difluoro-2-hydroxypropiophenone 
• 637040-89-2 (2R)-2-(1-ethoxyethoxy)-1-(2,4-difluorophenyl)-1-propanone 
• 161457-73-4 (R)-1-(2,4-Difluoro-phenyl)-2-trimethylsilanyloxy-propan-1-one 
• 247196-88-9 C₁₆H₁₄F₂O₂ 

Downstream Products

• 127001-03-0 (2R)-2',4'-Difluoro-2-(3,4,5,6-tetrahydro-2H-pyran-2-yloxy)propiophenone 
• 132507-89-2 (2R,3R)-2-(2,4-Difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-2,3-butanediol 
• 135133-23-2 (3R)-2-(2,4-difluorophenyl)-3-(tetrahydropyran-2-yloxy)-1-[1,2,4]triazol-1-yl-butan-2-ol 
• 135267-12-8 2-((R)-1-((R)-2-(2,4-difluorophenyl)oxiran-2-yl)ethoxy)tetrahydro-2H-pyran 
• 134779-41-2 (2R,3R)-2-(2,4-difluorophenyl)-3-(methylsulfonyl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol 
• 126918-20-5 (2R,3R)-2-(2,4-difluorophenyl)butane-1,2,3-triol 
• 124627-86-7 1-(((2R,3S)-2-(2,4-difluorophenyl)-3-methyloxiran-2-yl)-methyl)-1H-1,2,4-triazole 
• 126918-19-2 (2R,3R)-2-(2,4-Difluorophenyl)-3-(2-tetrahydropyranyloxy)-1,2-butanediol 
• 126917-48-4 (2R,3R)-3-Azido-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-2-butanol 
• 126918-18-1 (2S,3R)-2-(2,4-difluorophenyl)-1-(dimethylisopropoxysilyl)-3-(2-tetrahydropyranyloxy)-2-butanol 
• 126918-21-6 (2R,3R)-2-(2,4-difluorophenyl)-2-hydroxybutane-1,3-diyl dimethanesulfonate 
• 146071-45-6 1-(2,4-difluorophenyl)-1-hydroxy-2-propanone 
• 132563-81-6 1-(2,4-difluorophenyl)-2-(tetrahydropyranyloxy)propan-1-one 
• 126918-35-2 (1R)-1-<(2R)-2-(2,4-difluorophenyl)-2-oxiranyl>ethanol 

Relevant academic research and scientific papers

PROCESS FOR PRODUCING EPOXYTRIAZOLE COMPOUND AND INTERMEDIATE THEREFOR

The present invention provides a compound of the formula (I); wherein Ar represents difluorophenyl group, which is useful as an intermediate in a process for producing an epoxytriazole compound of the formula (VII); wherein Ar represents difluorophenyl group, which is a synthetic intermediate of antifungal agents. The present invention also provides a process for producing a compound of the formula (VII) which comprises epoxydation step, deprotection step, reaction step with a compound represented by RSO2X, and reaction step with 1,2,4-triazole; or comprises epoxydation step, reaction step with 1,2,4-triazole, deprotection step, reaction step with a compound represented by RSO2X and treatment step by a base.

Production methods of epoxytriazole derivative and intermediate therefor

An epoxytriazole derivative (V) useful as an intermediate for anti-fungal agents and an intermediate therefor having high quality can be produced economically and efficiently by the following industrial means. A compound of the following formula (I) is reacted with trimethyloxosulfonium salt and the like in the presence of a base to give compound (II), this compound is converted to compound (IV), and this compound is reacted with 1,2,4-triazole in the presence of a base. wherein Ar is a phenyl group optionally substituted by 1 to 3 halogen atom(s) or trifluoromethyl group, R is a hydrogen atom or lower alkyl group, and X is a leaving group.

Process for the preparation of 2-hydroxyalkyl halophenones

2-Benzyloxyalkyl halophenones of the formula (3): wherein X1and X2are each independently H, Cl or F, provided that at least one of X1and X2is Cl or F; one of R3and R4is H and the other is optionally substituted benzyloxy; and R5is an unsubstituted alkyl, preferably a C1-6alkyl group. The compounds are useful as intermediates for preparing 2-hydroxyalkyl halophenones.

Enantioselective Synthesis of α-Hydroxy Ketones via Benzaldehyde Lyase-Catalyzed C-C Bond Formation Reaction

(R)-Benzoins and (R)-2-hydroxypropiophenone derivatives are formed on a preparative scale by benzaldehyde lyase (BAL)-catalyzed C-C bond formation from aromatic aldehydes and acetaldehyde in aqueous buffer/ DMSO solution with remarkable ease in high chemical yield and high optical purity. The substrate range of this thiamin diphosphate-dependent enzyme was examined with respect to a broad applicability of this benzoin condensation-type reaction in stereoselective synthesis.

Simple chemoenzymatic access to enantiopure pharmacologically interesting (R)-2-hydroxypropiophenones

A chemoenzymatic synthesis of pharmacological interesting (R)-2-hydroxypropiophenones starting from propiophenone derivatives is described. Manganese(III) acetate-mediated acetoxylation followed by fungus-mediated hydrolysis of propiophenone derivatives affords (R)-2-hydroxypropiophenones in high enantiomeric excess.

Metal salts induced improved α-hydroxylation of ketones for the preparation of the key chiral intermediate of azole antifungals

The first example demonstrating the influence of metal salts for an improved synthesis of 2',4'-difluoro-(R)-2-hydroxypropiophenone, (2), a key intermediate for the preparation of azole antifungals such as Sch 42427 (1) in excellent enantiomeric excess and high chemical yield via the use of camphorsulfonyloxaziridines is described.

Total chiral synthesis of azole antifungals via α-hydroxylation of ketones

The use of camphorsulfonyl oxaziridines for the preparation of 2',4'-difluoro-(R)-2-hydroxypropiophenone, (2), a key intermediate for the synthesis of azole antifungals Sch 42427 and ER-30346 (1) in excellent enantiomeric excess and high chemical yield is described.

Preparations of antifungal Sch 42427/SM 9164: Preparative chromatographic resolution, and total asymmetric synthesis via enzymatic preparation of chiral α-hydroxy arylketones

Efficient approaches towards the preparation of chiral azole antifungals Sch 42427/SM 9164 (1) via large scale chromatographic separation of its enantiomers, or via enzymatic syntheses of key chiral intermediates α-hydroxy arylketones 5 in excellent enantiomeric excesses (ees) are described.

A rational approach to chiral α-hydroxy aryl ketones from chiral aryl epoxides via regioselective, stereo retentive oxidative epoxide opening: Its application to the synthesis of antifungal Sch 42427/SM 9164

A new, mild method for the direct conversion of chiral aryl epoxides to hydroxy-protected chiral α-hydroxy aryl ketones with complete retention of the chiral center and good regioselectivity has been established. An application of this new reaction to the synthesis of antifungal Sch 42427/SM 9164 is also described.

Optically active antifungal azoles. I. Synthesis and antifungal activity of (2R,3R)-2-(2,4-difluorophenyl)-3-mercapto-1-(1H-1,2,4-triazol-1-yl)-2- butanol and its stereoisomers

(2R,3R)-2-(2,4-Difluorophenyl)-3-mercapto-1-(1H-1,2,4-triazol-1-yl)-2- butanol [(2R,3R)-7] and its stereoisomers [(2S,3R)-, (2S,3S)- and (2R,3S)-7] were prepared from the optically active oxiranes 6 by a newly developed ring- opening reaction and evaluated for antifungal activity. The thiol (2R,3R)-7 showed extremely potent antifungal activity in vitro and in vivo. The optically active oxirane (2R,3S)-6, a useful intermediate for the synthesis of sulfur-containing antifungal azoles 5, was synthesized from methyl (R)- lactate [(R)-8] via eight steps in a stereocontrolled manner. The key step in the synthesis is the Grignard reaction of an amide derivative [(R)-12a] of (R)-lactic acid with 2,4-difluorophenyl-magnesium bromide (13).