66892-34-0

Usage

Uses

Used in Pharmaceutical Industry:
6-Fluoro-4-chromanone is used as a key intermediate in the hydantoin synthesis of irreversible aldose reductase inhibitors. These inhibitors play a crucial role in the development of treatments for various diseases, including diabetes and its complications.
Used in Environmental Analysis:
6-Fluoro-4-chromanone serves as an internal standard for investigating carbonyl emissions from gasoline-powered light-duty vehicles (LDVs) and heavy-duty diesel-powered vehicles. It is utilized in chromatography-mass spectrometry analyses to accurately measure and control the carbonyl emissions, contributing to environmental protection and air quality improvement.
Used in Analytical Chemistry:
In the field of analytical chemistry, 6-Fluoro-4-chromanone is employed as an internal standard for direct analysis of carbonyls in diesel emissions. It is used in conjunction with a new high-performance liquid chromatography (HPLC) technique with atmospheric pressure chemical ionization (APCI) mass spectrometry, enhancing the accuracy and efficiency of carbonyl detection and analysis in diesel emissions.

InChI:InChI=1/C10H7BF3.K/c12-11(13,14)10-6-5-8-3-1-2-4-9(8)7-10;/h1-7H;/q-1;+1

Upstream product

• 1579-78-8 3-(4-fluoro-phenoxy)propionic acid 
• 459-60-9 1-fluoro-4-methoxybenzene 
• 92-84-2 10H-phenothiazine 
• 79-10-7 acrylic acid 
• 50663-22-4 4-fluorophenyl acrylate 
• 394-32-1 1-(5-fluoro-2-hydroxyphenyl)ethan-1-one 
• 393-62-4 1-(3-bromo-5-fluoro-2-hydroxyphenyl)ethan-1-one 
• 133077-43-7 C₉H₈ClFO₂ 
• 372-20-3 3-fluorophenol 
• 844648-05-1 3-(3-fluorophenoxy)propanenitrile 
• 133077-42-6 3-(3-fluorophenoxy)propanoic acid 
• 105300-38-7 6-fluoro-4H-chromen-4-one 
• 90477-47-7 2,3-dihydro-6-fluoro-4H-ureido-1-benzopyran-4-carboxylic acid 
• 371-41-5 4-Fluorophenol 

Downstream Products

• 79791-44-9 (S)-2,3-dihydro-6-fluoro-4-<(1-phenylethyl)imino>-4H-1-benzopyran 
• 105799-69-7 4-chloro-6-fluoro-2H-benzo[1,2-b]pyran-3-carboxaldehyde 
• 93669-90-0 7-benzoyl-5-fluoro-2,3-dihydro-1-benzofuran-3-carboxylic acid 
• 93669-89-7 ethyl 7-benzoyl-5-fluoro-2,3-dihydrobenzofuran-3-carboxylate 
• 850799-82-5 (E)-6-fluoro-3-[1-phenyl-methylidene]-chroman-4-one 
• 69684-83-9 (+/-)-sorbinil 
• 1031206-39-9 (E)-6-fluoro-3-(3-hydroxy-4-methoxybenzylidene)chroman-4-one 
• 675602-87-6 3-benzylidene-6-fluoro-chroman-4-one 

Relevant academic research and scientific papers

Acid activated montmorillonite K-10 mediated intramolecular acylation: Simple and convenient synthesis of 4-chromanones

3-Aryloxyproionic acids undergo intramolecular cyclization in the presence of AA.Mont.K-10 in toluene under reflux for 30–45 min in good to excellent yields. Phenyl ring bearing various substituents at the ortho, meta, para positions undergo this cyclization reaction. This method involves simple work up and amenable for large scale preparations. The heterogeneous acid treated catalyst can be regenerated and used for up to three cycles with minimum loss of activity.

Oxidative Cleavage of Alkenes by O2with a Non-Heme Manganese Catalyst

The oxidative cleavage of C═C double bonds with molecular oxygen to produce carbonyl compounds is an important transformation in chemical and pharmaceutical synthesis. In nature, enzymes containing the first-row transition metals, particularly heme and non-heme iron-dependent enzymes, readily activate O2 and oxidatively cleave C═C bonds with exquisite precision under ambient conditions. The reaction remains challenging for synthetic chemists, however. There are only a small number of known synthetic metal catalysts that allow for the oxidative cleavage of alkenes at an atmospheric pressure of O2, with very few known to catalyze the cleavage of nonactivated alkenes. In this work, we describe a light-driven, Mn-catalyzed protocol for the selective oxidation of alkenes to carbonyls under 1 atm of O2. For the first time, aromatic as well as various nonactivated aliphatic alkenes could be oxidized to afford ketones and aldehydes under clean, mild conditions with a first row, biorelevant metal catalyst. Moreover, the protocol shows a very good functional group tolerance. Mechanistic investigation suggests that Mn-oxo species, including an asymmetric, mixed-valent bis(μ-oxo)-Mn(III,IV) complex, are involved in the oxidation, and the solvent methanol participates in O2 activation that leads to the formation of the oxo species.

Chemoselective Hydrosilylation of the α,β-Site Double Bond in α,β- And α,β,γ,δ-Unsaturated Ketones Catalyzed by Macrosteric Borane Promoted by Hexafluoro-2-propanol

The B(C6F5)3-catalyzed chemoselective hydrosilylation of α,β- and α,β,γ,δ-unsaturated ketones into the corresponding non-symmetric ketones in mild reaction conditions is developed. Nearly 55 substrates including those bearing reducible functional groups such as alkynyl, alkenyl, cyano, and aromatic heterocycles are chemoselectively hydrosilylated in good to excellent yields. Isotope-labeling studies revealed that hexafluoro-2-propanol also served as a hydrogen source in the process.

Facile access to chiral 4-substituted chromanes through Rh-catalyzed asymmetric hydrogenation

Rh/ZhaoPhos-catalyzed asymmetric hydrogenation of a series of (E)-2-(chroman-4-ylidene)acetates was successfully developed to prepare various chiral 4-substituted chromanes with high yields and excellent enantioselectivities (up to 99percent yield, 98percent ee). Moreover, the gram-scale hydrogenation could be performed well in the presence of 0.02 molpercent catalyst loading (TON = 5000), the hydrogenation product was easily converted to access other important compounds, which demonstrated the synthetic utility of this asymmetric catalytic methodology.

CHROMENE DERIVATIVES AS INHIBITORS OF TCR-NCK INTERACTION

The present invention provides compounds that modulate the interaction of TCR with Nck, compositions thereof, and methods of treatment using the same.

Synthesis of Flavanones via Palladium(II)-Catalyzed One-Pot β-Arylation of Chromanones with Arylboronic Acids

A total of 47 flavanones were expediently synthesized via one-pot β-arylation of chromanones, a class of simple ketones possessing chemically unactivated β sites, with arylboronic acids via tandem palladium(II) catalysis. This reaction provides a novel route to various flavanones, including natural products such as naringenin trimethyl ether, in yields up to 92percent.

Redox-Neutral Coupling between Two C(sp3)?H Bonds Enabled by 1,4-Palladium Shift for the Synthesis of Fused Heterocycles

The intramolecular coupling of two C(sp3)?H bonds to forge a C(sp3)?C(sp3) bond is enabled by 1,4-Pd shift from a trisubstituted aryl bromide. Contrary to most C(sp3)?C(sp3) cross-dehydrogenative couplings, this reaction operates under redox-neutral conditions, with the C?Br bond acting as an internal oxidant. Furthermore, it allows the coupling between two moderately acidic primary or secondary C?H bonds, which are adjacent to an oxygen or nitrogen atom on one side, and benzylic or adjacent to a carbonyl group on the other side. A variety of valuable fused heterocycles were obtained from easily accessible ortho-bromophenol and aniline precursors. The second C?H bond cleavage was successfully replaced with carbonyl insertion to generate other types of C(sp3)-C(sp3) bonds.

TRPV1 ANTAGONISTS

Disclosed herein are compounds of Formula (I), or pharmaceutically acceptable salts, solvates, prodrugs, salts of prodrugs, or combinations thereof, wherein R1, R2, R3, R4, and m are defined in the specification. Compositions comprising such compounds and methods for treating conditions and disorders using such compounds and compositions are also disclosed.

TRPV1 ANTAGONISTS

Disclosed herein are compounds of formula (I), or pharmaceutically acceptable salts, solvates, prodrugs, salts of prodrugs, or combinations thereof, wherein R1, R2, R3, R4, and m are defined in the specification. Compositions comprising such compounds and methods for treating conditions and disorders using such compounds and compositions are also disclosed.

Preparation of 6-substituted 4-chromanones

Disclosed is a practical and efficient process for preparing 6-substituted 4-chromanones from phenolic acrylate ester compounds derivable from para-substituted phenolic or thiophenolic compounds and beta-unsubstituted acrylic acid compounds which are esterifiable therewith. The process includes effecting rearrangement of a phenolic or thiophenolic acrylate ester in the presence of a rearrangement effective amount of hydrogen fluoride to the corresponding hydroxy - or mercapto (vinyl ketone) wherein the carbonyl carbon atom of the vinyl carboxy group is directly attached to the benzene ring ortho to the hydroxy or mercapto group. Thereafter, the vinyl ketone is cyclized to the corresponding 6-substituted 4-chromanone in the presence of a cyclization-effective amount of hydrogen fluoride. The 6-substituted 4-chromanones prepared by the process are useful as intermediates for preparing pharmaceutical agents.