59227-02-0

Basic information

• Product Name: 2-(4-fluorophenyl)cyclohexanone
• Synonyms: 2-(4-fluorophenyl)cyclohexanone
• CAS NO: 59227-02-0
• Molecular Formula: C₁₂H₁₃FO
• Molecular Weight: 192.2294232
• Mol File: 59227-02-0.mol

Chemical Properties

• Boiling Point: 292.3°C at 760 mmHg
• Flash Point: 127.1°C
• Appearance: /
• Density: 1.121g/cm³
• Vapor Pressure: 0.00185mmHg at 25°C
• Refractive Index: 1.521
• CAS DataBase Reference: 2-(4-fluorophenyl)cyclohexanone(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4-fluorophenyl)cyclohexanone(59227-02-0)
• EPA Substance Registry System: 2-(4-fluorophenyl)cyclohexanone(59227-02-0)

Safety Data

• Hazardous Substances Data: 59227-02-0(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
2-(4-fluorophenyl)cyclohexanone is used as an intermediate in organic synthesis for the production of various pharmaceuticals and other organic compounds.
Used in Medicinal Chemistry:
2-(4-fluorophenyl)cyclohexanone is used as a building block in medicinal chemistry to develop new pharmaceuticals with potential therapeutic applications.
Used in Pharmaceutical Development:
2-(4-fluorophenyl)cyclohexanone is used as a precursor in the development of new pharmaceuticals, particularly for its analgesic and anti-inflammatory properties.
Used in Material Science:
2-(4-fluorophenyl)cyclohexanone is used in the research and development of new materials and chemical processes, leveraging its unique structural and chemical properties.

InChI:InChI=1/C12H13FO/c13-10-7-5-9(6-8-10)11-3-1-2-4-12(11)14/h5-8,11H,1-4H2

Upstream product

• 872-53-7 cyclopentanealdehyde 
• 1765-93-1 4-fluoroboronic acid 
• 822-87-7 2-Chlorocyclohexanone 
• 460-00-4 1-Bromo-4-fluorobenzene 
• 533-60-8 cyclohexanone-2-ol 
• 130387-74-5 4-fluorophenylmagnesium chloride 
• 352-34-1 4-fluoro-1-iodobenzene 
• 108-94-1 cyclohexanone 
• 352-13-6 4-flourophenylmagnesium bromide 
• 286-20-4 cyclohexane-1,2-epoxide 
• 6651-36-1 1-(Trimethylsilyloxy)cyclohexene 
• 352-33-0 1-Chloro-4-fluorobenzene 
• 1736-67-0 4-fluorophenylacetaldehyde 
• 162011-79-2 1-(4-fluorophenyl)-5-hexen-2-one 

Downstream Products

• 1316848-57-3 2-(4-fluorophenyl)-1-(trimethylsiloxy)cyclohex-1-ene 
• 1375502-06-9 trifluoro-methanesulfonic acid 2-(4-fluoro-phenyl)-cyclohex-1-enyl ester 
• 1375502-08-1 2-chloro-4-[2-(4-fluoro-phenyl)-cyclohex-1-enyl]-pyridine 
• 1375502-12-7 4-[2-(4-fluoro-phenyl)-cyclohex-1-enyl]-pyridin-2-ylamine 
• 1375500-75-6 {4-[2-(4-fluoro-phenyl)-cyclohex-1-enyl]-pyridin-2-yl}-urea 

Relevant articles and documents

Selective C-C Bond Cleavage of Cycloalkanones by NaNO2/HCl

A novel selective fragmentation of cycloalkanones by NaNO2/HCl has been established. The C-C bond cleavage reaction proceeds smoothly under mild conditions, selectively affording versatile keto acids or oxime acids. The methodology can streamline the synthesis of valuable chiral molecules and isocoumarins from readily available feedstocks.

The Silicon-Hydrogen Exchange Reaction: Catalytic Kinetic Resolution of 2-Substituted Cyclic Ketones

We have recently reported the strong and confined, chiral acid-catalyzed asymmetric 'silicon-hydrogen exchange reaction'. One aspect of this transformation is that it enables access to enantiopure enol silanes in a tautomerizing σ-bond metathesis, via deprotosilylation of ketones with allyl silanes as the silicon source. However, until today, this reaction has not been applied to racemic, 2-substituted, cyclic ketones. We show here that these important substrates readily undergo a highly enantioselective kinetic resolution furnishing the corresponding kinetically preferred enol silanes. Mechanistic studies suggest the fascinating possibility of advancing the process to a dynamic kinetic resolution.

NMDA receptor antagonist and use thereof

The present invention relates to an NMDA receptor antagonist and use thereof. The NMDA receptor antagonist is a compound as shown in the formula I, and pharmaceutically acceptable salts, enantiomers, diastereoisomers, tautomers, solvates, isotope substitutes, polymorphic substances, prodrugs or metabolites thereof, and in the formula, ring A, ring B and R2 are as described in the specification. The invention also provides pharmaceutical compositions containing the compounds, and applications of the compounds in preparation of drugs for treating or preventing NMDA receptor mediated diseases.

Aromatic compound, preparation method and use of aromatic compound

The invention relates to an aromatic compound, a preparation method and use of the aromatic compound, andspecifically discloses a compound represented by the following formula (I), or a tautomer or anenantiomer or a diastereomer or a racemate of the compound or a mixture of the compound or a pharmaceutically acceptable salt of the compound. The invention further discloses a preparation method ofthe compound and application of the compound in treating nervous systemdiseases.

Ylide-Functionalized Phosphine (YPhos)-Palladium Catalysts: Selective Monoarylation of Alkyl Ketones with Aryl Chlorides

Ylide-functionalized phosphine (YPhos) ligands allow the palladium-catalyzed α-arylation of alkyl ketones with aryl chlorides with record setting activity. Using a cyclohexyl-substituted YPhos ligand, a wide range of challenging ketone substrates was efficiently and selectively monoarylated under mild conditions. A newly designed YPhos ligand bearing tert-butyl groups on the coordinating phosphorus atom is already active at room temperature. The synthetic potential was demonstrated by gram-scale reactions and the succinct synthesis of ?-caprolactone derivatives.

Catalytic allylic oxidation to generate vinylogous acyl sulfonates from vinyl sulfonates

Regioselective formation of vinylogous acyl sulfonates was accomplished via the allylic oxidation of the corresponding vinyl sulfonates. The reaction progressed through the agency of catalytic iron(III) chloride catalysis with tert-Butyl hydroperoxide (TBHP) as the stoichiometric oxidant. Tolerance of other functional groups, including some other allylic and benzylic sites, was observed.

Enantioselective Protonation of Silyl Enol Ethers Catalyzed by a Chiral Pentacarboxycyclopentadiene-Based Bronsted Acid

The enantioselective protonation of silyl enol ethers was realized in the presence of a pentacarboxycyclopenta-1,3-diene-based chiral Bronsted acid catalyst with water as an achiral proton source to give the corresponding α-aryl ketones in good yields and up to 75percent ee.

Synthesis of α-Arylated Cycloalkanones from Congested Trisubstituted Spiro-epoxides: Application of the House-Meinwald Rearrangement for Ring Expansion

A three-step sequence for the synthesis of α-arylated cyclohexanones and the most challenging cycloheptanones is reported. First, an efficient one-pot synthesis of β,β'-disubstituted benzylidene cycloalkanes (styrenes) using the palladium-catalyzed Barluenga reaction from readily available feedstock chemicals is described. Furthermore, an epoxidation followed by the House-Meinwald rearrangement (HMR) of spiro-epoxides is reported to produce a number of α-arylated cycloalkanones upon ring expansion. Reactions catalyzed by bismuth triflate underwent quasi-exclusively ring expansion for all substrates (electronically poor and rich), with yields ranging from 15% to 95%, thus demonstrating the difficulty of achieving ring enlargement for electron-deficient spiro-epoxides. On the other hand, by means of catalysis with aluminum trichloride, the rearrangement of spiro-epoxides proceeded typically in high yields and with remarkable regioselectivity on a broader substrate scope. In this case, a switch of regioselectivity was achieved for spiro-epoxides with electron-withdrawing substituents which enable the method to be successfully extended to some chemospecific arene shifts and the synthesis of aldehydes bearing a α-quaternary carbon. While the HMR has been extensively studied for smaller ring enlargement, we are pleased to report herein that larger cyclohexanones and cycloheptanones can be obtained efficiently from more sterically demanding trisubstituted spiro-epoxides bearing electron-releasing and electron-neutral arene substituents.

p-Toluenesulfonic acid catalysed fluorination of α-branched ketones for the construction of fluorinated quaternary carbon centres

A p-toluenesulfonic acid catalyzed fluorination of α-branched ketones for the construction of fluorinated quaternary carbon centers has been developed, featuring a broad substrate scope, environmentally benign reaction conditions, and operational simplicity.

Regioselective 1,2-Diol Rearrangement by Controlling the Loading of BF3·Et2O and Its Application to the Synthesis of Related Nor-Sesquiterene- and Sesquiterene-Type Marine Natural Products

The regiocontrolled rearrangement of 1,2-diols has been achieved by controlling the loading of BF3·Et2O. Its applicability is showcased by the divergent synthesis of austrodoral, austrodoric acid, and 8-epi-11-nordriman-9-one, as well as a formal synthesis of siphonodictyal B and liphagal. A new light is shed on piancol-type rearrangements that will be useful in diversity-oriented synthesis of related natural products.