186410-79-7

Basic information

• Product Name: 1-Propanone, 2-fluoro-1-(4-methoxyphenyl)-, (R)- (9CI)
• Synonyms: 1-Propanone, 2-fluoro-1-(4-methoxyphenyl)-, (R)- (9CI)
• CAS NO: 186410-79-7
• Molecular Formula: C10H11FO2
• Molecular Weight: 182.1915432
• Product Categories: ACETYLHALIDE
• Mol File: 186410-79-7.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1-Propanone, 2-fluoro-1-(4-methoxyphenyl)-, (R)- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Propanone, 2-fluoro-1-(4-methoxyphenyl)-, (R)- (9CI)(186410-79-7)
• EPA Substance Registry System: 1-Propanone, 2-fluoro-1-(4-methoxyphenyl)-, (R)- (9CI)(186410-79-7)

Safety Data

• Hazardous Substances Data: 186410-79-7(Hazardous Substances Data)

Upstream product

• 430-97-7 (R,S)-2-Fluoropropanoyl chloride 
• 100-66-3 methoxybenzene 
• 121-97-1 4-Methoxypropiophenone 
• 100-07-2 4-methoxy-benzoyl chloride 
• 74-88-4 methyl iodide 
• 4180-23-8 E-1-(4'-methoxyphenyl)prop-1-ene 

Relevant articles and documents

Bench-Stable Electrophilic Fluorinating Reagents for Highly Selective Mono- and Difluorination of Silyl Enol Ethers

Efficient methods for the synthesis of fluorinated compounds have been intensively studied, recently. Development of practical fluorinating reagents is indispensable for this purpose. Herein, bench-stable electrophilic fluorinating reagents were synthesized as N-fluorobenzenesulfonimide (NFSI) substitutes. Reagents obtained by replacing one of the NFSI sulfonyl groups with an acyl group led to the highly selective monofluorination of silyl enol ethers with suppression of undesired overreaction, that is, difluorination. On the other hand, reagents bearing electron-withdrawing substituents at NFSI benzenesulfonyl groups efficiently facilitated the difluorination of silyl enol ethers under base-free conditions. Thus, both mono- and difluorinated target materials were prepared from the same substrate.

Iridium-Catalyzed Asymmetric Hydrogenation of α-Fluoro Ketones via a Dynamic Kinetic Resolution Strategy

The discrimination of a fluorine atom from a hydrogen atom has been challenging in asymmetric catalysis. We herein report iridium-catalyzed hydrogenation of α-fluoro ketones using a strategy of dynamic kinetic resolution. Both enantiomeric and diastereomeric selectivities were satisfactory in the preparation of β-fluoro alcohols. The DFT calculation revealed a C-F···Na charge-dipole interaction in the transition state of hydride transfer. This noncovalent interaction would be responsible for the diastereomeric control.

α,α-Alkylation-Halogenation and Dihalogenation of Sulfoxonium Ylides. A Direct Preparation of Geminal Difunctionalized Ketones

A one-pot alkylation–halogenation of ketosulfoxonium ylides in the presence of alkyl halides is described. The method furnishes several gem-difunctionalized haloketones (an alkyl and F, Cl, Br, or I) in good yields. Replacing alkyl halides with a mixture of electrophilic halogen species and various halide anions led to gem-dihalogenated ketones containing a combination of the same or two different halogens. Kinetic isotopic effects as well as reaction kinetic experiments give insight to the mechanism of these reactions.

Synthesis of α-Fluoroketones from Vinyl Azides and Mechanism Interrogation

An efficient and mild fluorination of vinyl azides for the synthesis of α-fluoroketones is described. The mechanistic studies indicated that a single-electron transfer (SET) and a subsequent fluorine atom transfer process could be involved in the reaction.

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.

Chiral benzylic carbocations: Low-temperature NMR studies and theoretical calculations

(Chemical Equation Presented) The α-chiral secondary and tertiary benzylic carbocations 19-30 were generated from the corresponding benzylic alcohols 1, 2, and 5-14 by treatment with FSO3H or FSO 3H/SbF5 in SO2ClF as the solvent at -70°C and characterized by one- and two-dimensional NMR spectroscopy. Coupling constants and NOESY measurements suggest a preferred conformation in which the α-hydrogen atom occupies the 1,3-allylic-strain position and the diastereotopic faces of the cations are differentiated by the alkyl substituent and a functional group (FG). The existence of this preferred conformation is further supported by calculations using a DFT method at the B3LYP/6- 311+G** level. Quenching experiments with an arene nucleophile showed a preferential attack from the less shielded diastereotopic face delivering high diastereomeric ratios, supporting the hypothesis that these carbocations are involved as intermediates in previously studied SN1 reactions. A strong shielding effect at the benzylic carbocationic center is observed for most of the secondary benzylic carbocations (derived from precursors 5-13) investigated, indicating a strong mesomeric distribution of the positive charge to the carbon atom in the para-position of the anisyl substituent. For α-halogen-substituted carbocations (5-7, 12), no neighboring halogen participation leading to halonium ion formation was observed.

Synthesis of optically active (2-fluoroacyl)benzenes

Optically active (2-fluoroacyl)benzenes 1 which form a new class of compounds can be easily prepared from optically active 2-fluorocarboxylic acid chlorides 2 in high optical yield via Friedel-Crafts reaction using anhydrous iron trichloride as catalyst.