1755-11-9

Usage

Uses

Used in Organic Chemistry:
Cycloheptanone, 2-fluorois used as a building block in the synthesis of various organic compounds. Its unique structure allows for the creation of a wide range of chemical products, making it a valuable component in the field of organic chemistry.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, Cycloheptanone, 2-fluorois used as an intermediate in the development and production of specialty pharmaceutical products. Its unique properties and structure contribute to the creation of innovative and effective medications.
Used in Medicinal Chemistry:
Cycloheptanone, 2-fluorois employed in medicinal chemistry for its potential applications in drug discovery. Its unique structure and properties make it a promising candidate for the development of new drugs and therapeutic agents.
Used in Drug Synthesis:
Cycloheptanone, 2-fluorois used as a key component in the synthesis of various pharmaceuticals. Its presence in the molecular structure can enhance the activity and efficacy of the resulting drug compounds, making it an essential part of the drug development process.

Upstream product

• 15419-61-1 2-acetylcycloheptanone 
• 14477-74-8 1-cycloheptenyl acetate 
• 502-42-1 cycloheptanone 
• 68823-71-2 Cycloheptylidene-isopropyl-amine 
• 774-05-0 ethyl cycloheptanone-2-carboxylate 
• 766-66-5 2-chlorocycloheptanone 
• 15344-40-8 8-Oxa-bicyclo[5.1.0]octane-1-carbonitrile 
• 22631-01-2 1-Fluor-2-oxo-cycloheptancarbonsaeureaethylester 

Downstream Products

• 1373496-41-3 diethyl (1-ethynyl-2-fluorocycloheptyl)phosphate 

Relevant academic research and scientific papers

Mild and selective α-fluorination of carbonyl compounds (ketones, 1,3-diketones, β-ketoesters, α-nitroketones, and β-ketonitriles) with Selectfluor (F-TEDA-BF4) in imidazolium ILs [BMIM/PF6 or BMIM/NTf2] with Br?nsted-acidic IL [PMIM(SO3H)/OTf] as promoter

Structurally diverse ketones, 1,3-diketones, and β-ketoesters, were selectively monofluorinated with Selectfluor (F-TEDA-BF4) (1 equiv) in [BMIM][PF6] as solvent and [PMIM(SO3H)][OTf] as promoter under mild conditions. In selected cases, the monofluorinated products were transformed to the gem-difluoro derivatives by employing an additional equivalent of Selectfluor, and gem-difluoro-derivatives were synthesized directly from the substrates by employing 2 equiv of Selectfluor. The method was extended to monofluorination of representative α-nitroketones and β-ketonitriles using [BMIM][NTf2] without the need for promoters. The described method offers the added advantage of recycling and reuse of the IL solvent. (Chemical Equation Presented).

Stereocontrolled 1,3-phosphatyloxy and 1,3-halogen migration relay toward highly functionalized 1,3-dienes

A double migratory cascade reaction of α-halogen-substituted propargylic phosphates to produce highly functionalized 1,3-dienes has been developed. This transformation features 1,3-phosphatyloxy group migration followed by 1,3-shifts of bromine and chlorine as well as the unprecedented 1,3-migration of iodine. The reaction is stereodivergent: (Z)-1,3-dienes are formed in the presence of a copper catalyst, whereas gold-catalyzed reactions exhibit inverted stereoselectivity, producing the corresponding E products.

Infrared and theoretical calculations in 2-halocycloheptanones conformational analysis

2-Halocycloheptanones (Halo = F, Cl, Br and I) were synthesized and their conformational analysis was performed through infrared spectroscopy data. The corresponding conformers geometries and energies were obtained by theoretical calculations at B3LYP/aug-cc-pVDZ level of theory in the isolated state and in solution. It was observed, by both approaches, that the conformational preferences were very sensitive to the solvent polarity, since its increase led to an increase in the population of the more polar conformer. An analysis of these conformational equilibria showed they suffer also the influence of stereoelectronic effects, like hyperconjugation and steric effects. These results were interpreted using natural bond orbital (NBO) analysis, which indicated that the electronic delocalization to the orbital π* CO is directly involved in the stability increase of conformers I and II. The relative effect of the period of the halogen can also be noted, with changes in the conformational preferences and in the energies involved in the interactions of NBO.

Enantioselective organocatalytic α-fluorination of cyclic ketones

The first highly enantioselective α-fluorination of ketones using organocatalysis has been accomplished. The long-standing problem of enantioselective ketone α-fluorination via enamine activation has been overcome via high-throughput evaluation of a new library of amine catalysts. The optimal system, a primary amine functionalized Cinchona alkaloid, allows the direct and asymmetric α-fluorination of a variety of carbo- and heterocyclic substrates. Furthermore, this protocol also provides diastereo-, regio-, and chemoselective catalyst control in fluorinations involving complex carbonyl systems.

Discovery of 2-chloro-N-((4,4-difluoro-1-hydroxycyclohexyl)methyl)-5-(5-fluoropyrimidin-2-yl)benzamide as a potent and CNS penetrable P2X7 receptor antagonist

Focused SAR studies were carried out around 5-heteroaryl and 1-amide portions of the 2-chlorobenzamide scaffold, resulting in the discovery of a potent, metabolically stable and centrally penetrable antagonist against P2X7 receptor.

Micellar-system-mediated direct fluorination of ketones in water

A micellar system was developed and applied for direct regioselective fluorination of a variety of cyclic and acyclic ketones to α-fluoroketones in water as reaction medium with Selectfluor F-TEDA-BF4 as fluorinating reagent. The inexpensive ionic amphiphile sodium dodecyl sulfate (SDS) was found to be an excellent promoter for fluorofunctionalization of hydrophobic ketones without prior activation or use of acid catalysts. Georg Thieme Verlag Stuttgart.

Direct electrophilic α-fluorination of imines: Efficient synthesis of mono-and difluoroimines

(Chemical Equation Presented) A mild and efficient procedure to synthesize α-fluoro- and α,α-difluoroimines was developed. Various N-alkylimines derived from acetophenones were successfully monofluorinated using NFSI (N-fluorobenzenesulfonimide) in a mixture of CH3CN and DMF at 0°C. Alternatively, the same procedure without DMF gave rise to difluorinated imines when performed at room temperature. The obtained α- and α,α-difluorinated imines were subsequently reduced to give the corresponding β-fluoro- and β,β-difluoroamines in good yield.

High yield direct fluorofunctionalisation of ketones using accufluor - NFTh fluorinating reagent

Direct regioselective conversion of a variety of cyclic and acyclic ketones to α-fluoroketones was achieved in high to excellent yield using 1-fluoro-4-hydroxy-1,4-diazoniabicyclo[2,2,2]octane bis(tetrafluoroborate) [Accufluor - NFTh] in acetonitrile solution. Copyright

CHEMISTRY OF ORGANO HALOGENIC MOLECULES. PART 100. COMPARATIVE BEHAVIOUR OF XENON DIFLUORIDE AND CAESIUM FLUOROXYSULPHATE IN THE FLUORINATION OF ENOL ACETATES AND KETONES

Xenon difluoride and caesium fluoroxysulphate reacted in methylene chloride or acetonitrile with various enol acetates, diketones, and ketones, yielding mainly α-fluoro ketones, the course of the reaction depending on the reagent and the structure of the organic molecule.Enol acetates from cycloalkanones were converted with caesium fluoroxysulphate to α-fluoroxycycloalkanones in high yield.Xenon difluoride and caesium fluoroxysulphate converted enol acetates of benzocycloalkanones-1 to α-fluorobenzocycloalkanones, while the reactivity of enol acetates of benzocycloalkanones-2 depended on the reagent used. 1,3-Diphenyl-propane-1,3-dione and its enol acetate were converted with XeF2 and CsSO4F to mono and difluoro substituted products, the course of the reaction being dependent on the reagent.Xenon difluoride converted 1-indanone to rearranged 2,2-difluorochromane, while caesium fluoroxysulphate reacted to 1-fluoro-2-indanone with 2-indanone.