71019-06-2

Usage

Uses

Used in Chemical Synthesis:
1(2H)-Naphthalenone, 2-fluoro-3,4-dihydrois used as an intermediate in the chemical synthesis of other compounds. Its unique structure and properties allow for the creation of new materials and pharmaceutical drugs.
Used in Pharmaceutical Applications:
In the pharmaceutical industry, 1(2H)-Naphthalenone, 2-fluoro-3,4-dihydrois used as a building block for the development of new drugs. Its chemical structure can be modified and combined with other molecules to create potential therapeutic agents.
Used in Material Development:
1(2H)-Naphthalenone, 2-fluoro-3,4-dihydrois also utilized in the development of new materials due to its unique chemical properties. It can be incorporated into various formulations to enhance their performance or introduce new functionalities.

Upstream product

• 19455-84-6 3,4-dihydronaphthalen-1-yl acetate 
• 84716-82-5 4-methoxy-1,2-dihydronaphthalene 
• 146514-98-9 tert-butyl hypofluorite 
• 38858-72-9 1-trimethylsiloxy-3,4-dihydronaphthalene 
• 928768-24-5 (2-fluoro-3,4-dihydronaphthalen-1-yloxy)trimethylsilane 
• 106-38-7 para-bromotoluene 
• 624-31-7 4-tolyl iodide 
• 108-86-1 bromobenzene 
• 99-90-1 para-bromoacetophenone 
• 1221794-77-9 tri-n-propyl(2-fluoro-3,4-dihydronaphthalen-1-yloxy)silane 

Downstream Products

• 529-34-0 3,4-dihydronaphthalene-1(2H)-one 
• 247913-25-3 2-fluoro-2-(3-methyl-benzyl)-3,4-dihydro-2H-naphthalen-1-one 
• 247913-26-4 (S)-2-fluoro-2-(4-methylbenzyl)-3,4-dihydro-2H-naphthalen-1-one 
• 247913-27-5 2-(4-bromo-benzyl)-2-fluoro-3,4-dihydro-2H-naphthalen-1-one 
• 247913-24-2 2-fluoro-2-(2-methyl-benzyl)-3,4-dihydro-2H-naphthalen-1-one 
• 247913-11-7 (S)-2-benzyl-2-fluoro-3,4-dihydro-2H-naphthalen-1-one 

Relevant academic research and scientific papers

The Electrophilic Fluorination of Enol Esters Using SelectFluor: A Polar Two-Electron Process

The reaction of enol esters with SelectFluor is facile and leads to the corresponding α-fluoroketones under mild conditions and, as a result, this route is commonly employed for the synthesis of medicinally important compounds such as fluorinated steroids. However, despite the use of this methodology in synthesis, the mechanism of this reaction and the influence of structure on reactivity are unclear. A rigorous mechanistic study of the fluorination of these substrates is presented, informed primarily by detailed and robust kinetic experiments. The results of this study implicate a polar two-electron process via an oxygen-stabilised carbenium species, rather than a single-electron process involving radical intermediates. The structure–reactivity relationships revealed here will assist synthetic chemists in deploying this type of methodology in the syntheses of α-fluoroketones.

Palladium-Catalyzed Enantioselective α-Arylation of α-Fluoroketones

The transition-metal-catalyzed α-arylation of carbonyl compounds is a widely practiced method for C-C bond formation. Several enantioselective versions of this process have been reported, but intermolecular, enantioselective coupling reactions of aryl electrophiles with α-fluoro carbonyl compounds have yet to be disclosed. We report enantioselective coupling of aryl and heteroaryl bromides and triflates with α-fluoroindanones catalyzed by palladium complexes of a BINOL-derived monophosphine and Segphos, respectively. The enolates were generated directly from α-fluoroindanones in the presence of potassium phosphate base during the reactions. We also report that reactions of α-fluorotetralones occur in high yields and enantioselectivities when conducted with enolates generated by elimination of trifluoroacetate from trifluoromethyl β-diketone hydrates. These reactions were catalyzed by palladium complexes of the commercially available bisphosphine Difluorphos. Thus, the formation of enantioenriched α-aryl-α-fluoroketones can be readily achieved by C-C bond formation when the appropriate palladium catalyst and α-fluoro enolate precursor were used.

Impact of silyl enol ether stability on palladium-catalyzed arylations

The effect of stability on arylation of silyl enol ethers as dictated by the presence of bulky silyl groups was elucidated through experiment and calculation. With the enhancement of stability of the silyl enol ethers, especially of acyclic ethers, the ef

Pd-catalyzed arylation of silyl enol ethers of substituted α-fluoroketones

α-Fluoro-α-aryl-ketones were synthesized by the Pd-catalyzed cross-coupling of aryl bromides with either α-fluoroketones or their corresponding silyl enol ethers. The direct arylation with an α-fluoroketone requires a strong base, such as potassium tert-b

Reaction of silyl enol ethers with xenon difluoride in MeCN: Evidence for a nonclassical radical cation intermediate

(matrix presented). The reactions of xenon difluoride in MeCN solution in Pyrex flasks with a series of TMS enol ethers have been investigated. The types of products formed are dependent on the structures of individual enol ethers, but under these conditions all products are consistent with a mechanism involving single electron transfer to un-ionized XeF2 giving a radical cation and subsequent formation of an α-fluoroketone, together with some ketone formation. The results suggest that if the radical cation is particularly stable, fluorodesilylation leads to radical formation, and solvent-derived products are then observed. Using other solvents, such as CFCl3 and C6F6, much more complex mixtures of products are obtained, and this is attributed to a different mode of reaction of xenon difluoride involving ionization to FXe+.

Tert-Butyl Hypofluorite - An Electrophilic tert-Butoxylation Agent

tert-Butyl hypofluorite, t-BuOF, easily synthesized from Z-BuOH and F2, is a unique source of the novel electrophilic tert-butoxylium moiety t-BuO+. It was added to several benzylic double bonds to form vicinal fluoro-tert-butoxide derivatives. Not surprisingly, this bulky reagent is quite sensitive to steric hindrance. The process is electrophilic in nature, but since the reaction is relatively slow (20-60 min) formation of various radical species can take place, forming eventually several distinct byproducts. t-BuOF was also reacted with a number of enols, producing the corresponding α-tert-butoxy ketone derivatives in moderate to good yields. The best results were obtained with benzylic enol derivatives.

Obtention d'α-fluorocetones par oxydation anodique de derives d'enol.

To obtain fluoroketones without the use of electrophilic fluorinating reagents, we have carried out the anodic oxidation of enol esters and enol ethers in acetonitrile/Et3N, 3HF solution.With enol esters the main product is a fluoroketone or an acetoxyketone respectively, depending on the structure of the starting compound.The enol ether cation-radicals seemed to be less reactive towards H2F3- ions than the corresponding enol ester ones.

UN NOUVEAU MODE D'ACCES AUX Α-FLUOROCETONES: L'OXYDATION ANODIQUE DES ACETATES D'ENOL EN PRESENCE D'IONS FLUORURES

We describe a new route to α-fluoroketones: anodic oxidation of enol-acetates in presence of Et3N, 3HF as agent of fluorination and supporting-electrolyte.