1524-06-7

Usage

Type of compound

Fluorinated ketone

Structural features

Contains a phenyl group attached to the carbon chain

Fluorine atom

Makes it a useful building block in organic chemistry

Applications

a. Synthesis of pharmaceuticals
b. Synthesis of other organic compounds
c. Potential applications in medicinal chemistry

Versatility

Offers a wide range of possibilities for use in different industries and research fields

Upstream product

• 459-72-3 ethyl 2-fluoroacetate 
• 1589-82-8 phenylmagnesium bromide 
• 157336-59-9 1-Benzenesulfinyl-1-fluoro-3-phenyl-propan-2-ol 
• 175399-98-1 2-benzyl-2-fluorooxirane 
• 66622-72-8 (2-fluoroprop-2-enyl)benzene 
• 503-20-8 fluoroacetonitrile 
• 100-59-4 phenylmagnesium chloride 
• 25832-09-1 3-oxo-4-phenyl-butyric acid 
• 122-78-1 phenylacetaldehyde 
• 4982-08-5 1-hydroxy-3-phenylpropan-2-one 

Downstream Products

• 701-71-3 (+/-)-α-(fluoromethyl)benzeneethanol 
• 67835-08-9 1,5-Diphenyl-4-fluormethyl-4-hydroxy-3-fluorpentan-2-on 
• 110270-43-4 (S)-α-(fluoromethyl)benzeneethanol 

Relevant academic research and scientific papers

(S)-ALPHA-FLUOROMETHYLTYROSINE AS DECARBOXYLASE INHIBITORS FOR USE IN THE TREATMENT OF HYPOTENSION

Provided are methods of using and drug delivery systems comprising inhibitors of pathogenic, bacterial metabolite production and conjugates of the inhibitors.

Deoxyfluorination of alcohols with aryl fluorosulfonates

Aryl fluorosulfonates are developed as a deoxyfluorinating reagent in the transformation of primary and secondary alcohols into the corresponding alkyl fluorides. These reagents feature easy availability, low-cost, high stability and high efficiency. Diverse functionalities including aldehyde, ketone, ester, halogen, nitro, alkene, and alkyne are well tolerated under mild reaction conditions.

A Practical Synthesis of α-Fluoroketones in Aqueous Media by Decarboxylative Fluorination of β-Ketoacids

A practical and novel process for the decarboxylative fluorination of β-ketoacids in water in the presence of phase transfer catalyst has been developed, affording a series of α-fluoroketones in good to excellent yields. Furthermore, a preliminary investigation for the catalytic asymmetric transformation was performed and a proposed mechanistic pathway for this catalytic process was proposed.

Activation of pig liver esterase in organic media with organic polymers. Application to the enantioselective acylation of racemic functionalized secondary alcohols

Pig liver esterase (PLE) shows practically no activity in acylation of alcohols with vinylic esters in organic solvents. However, addition of methoxypoly(ethylene glycol) (MPEG), bovine serum albumin (BSA), TentaGelAmino resin (TGA), or aminomethyl polystyrene (AMPS) confers activity to PLE in acylation of alcohols with vinyl propionate in organic solvents of low water content. Polymer-activated PLE showed high enantioselectivities (E > 100) in the acylation of racemic 1-alkoxy-, 1-ethylsulfanyl-, and 1-fluoro-3-aryl-2-propanols as well as racemic 1-phenoxy-2-propanol and racemic 1-methoxy-2-phenoxy-2-propanol. The synthetic utility of polymer-activated PLE has been demonstrated by the gram-scale resolution of 1-methoxy-3-phenyl-2-propanol, 1-ethylsulfanyl-3-phenyl-2-propanol, 1-methoxy-3-p-methoxyphenyl-2-propanol, 1- fluoro-3-phenyl-2-propanol, and 1-methoxy-3-phenoxy-2-propanol. In PLE-catalyzed acylation of alcohols with vinyl propionate, acetaldehyde and propionic acids, both being detrimental to the enzyme, are formed as byproducts. In addition, the water content of the system, which is critical for the activity of pig liver esterase, is lowered because of a competing enzymatic hydrolysis of the acyl donor. The polymers TGA, BSA, and AMPS not only scavenge the aldehyde and the acid through imine formation and neutralization, respectively, but replenish at least in part also the water consumed in the competing hydrolysis of the acyl donor. A recovery of PLE together with the polymer was achieved without major loss of activity through their immobilization on a water-saturated polyaramide membrane, which occurs spontaneously in organic solvents.

α-Fluorocarbonyl compounds by isomerization of 2-fluorooxiranes

2-Fluorooxiranes 2 can be isolated after peracid oxidation of fluoroalkenes 1. When treated with the triethylamine hydrogen fluoride adduct, the intermediates 2 isomerize to afford α-fluorinated carbonyl compounds 3.

An improved procedure for the synthesis of fluoromethylketones: Flash vacuum pyrolytic elimination

Fluoromethylketones 3 are synthesized in good yields by a flash vacuum pyrolytic elimination of 2. Studies on the improved synthesis of 2 leads to the evidence on the existence of α,α-dilithio fluoromethyl phenyl sulfoxide.

A Novel Method for the Synthesis of α-Fluoroketones via Claisen Rearrangement

Fluorine-facilitated Claisen rearrangement has been employed as a key step in the synthesis of α-fluoroketones 5.The elimination of sulfenic acid from the allyl ethers 3 are effected under FVP conditions.