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Usage

Uses

Used in Pharmaceutical Industry:
4H-1-Benzopyran-4-one,6-fluorois used as a key intermediate in the synthesis of various chromone derivatives with potential pharmaceutical applications. These derivatives may exhibit a range of biological activities, such as anti-inflammatory, antioxidant, and anticancer properties.
Used in Chemical Synthesis:
In the field of organic chemistry, 4H-1-Benzopyran-4-one,6-fluoroserves as a versatile building block for the synthesis of a variety of chromone-based compounds. These compounds can be further modified to explore their potential applications in various industries.
Specifically, 6-Fluorochromone may be used to synthesize the following chromone derivatives:
1. 6-fluoro-3-[hydroxy(6-methylpyridin-2-yl)methyl]chromone: This chromone derivative may be synthesized for potential applications in medicinal chemistry, where it could be further studied for its biological activities and potential therapeutic uses.
2. 6-fluoro-3-[hydroxy(pyridin-2-yl)methyl]chromone: 4H-1-Benzopyran-4-one,6-fluoromay be of interest in the development of new pharmaceutical agents, as it could possess unique properties due to the presence of the fluorine atom and the pyridin-2-ylmethyl group.
3. 6-fluoro-3-[hydroxy(quinolin-2-yl)methyl]chromone: The synthesis of this chromone derivative may lead to the discovery of new compounds with potential applications in various fields, such as pharmaceuticals, materials science, or agrochemicals.

Upstream product

• 394-32-1 1-(5-fluoro-2-hydroxyphenyl)ethan-1-one 
• 4637-24-5 N,N-dimethyl-formamide dimethyl acetal 
• 109-94-4 formic acid ethyl ester 
• 928773-42-6 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)chromen-4-one 
• 66892-34-0 6-fluoro-4-chromanone 

Downstream Products

• 1384433-42-4 2-(6-fluoro-4-oxo-4H-chromen-3-yl)cyclohexa-2,5-diene-1,4-dione 
• 1218-82-2 6-fluoro-2-phenylchromen-4-one 
• 1220893-39-9 6-fluoro-2-phenylchroman-4-one 
• 111478-09-2 6-fluoro-2-benzylchroman-4-one 
• 66892-34-0 6-fluoro-4-chromanone 
• 409346-73-2 6-fluoro-3,4-dihydro-2H-1-benzopyran-2-carboxaldehyde 
• 1619229-12-7 (Z)-5-(1,2-diphenylvinyl)-6-fluoro-4H-chromen-4-one 

Relevant academic research and scientific papers

Silanediol-Catalyzed Chromenone Functionalization

Promising levels of enantiocontrol are observed in the silanediol-catalyzed addition of silyl ketene acetals to benzopyrylium triflates. This rare example of enantioselective, intermolecular chromenone functionalization with carbonyl-containing nucleophiles has potential applications in the synthesis of bioactive chromanones and tetrahydroxanthones.

An Efficient Microwave-Assisted Propylphosphonic Anhydride (T3P )-Mediated One-Pot Chromone Synthesis via Enaminones

An efficient synthesis of 4 H -chromene-4-ones via enamino ketones, with cyclization by using T3P under microwave heating is described. This is the first report for the synthesis of chromones by using T3P . Significant features of this method include short reaction times and high-purity products.

NHC-catalyzed enantioselective C2-functionalization of 3-hydroxychromenonesviaα,β-unsaturated acyl azoliums

A novel synthetic method for enantioselective C2-functionalization of 3-hydroxychromenones promoted by N-heterocyclic carbenesviathe formation of α,β-unsaturated acyl azolium intermediates, which occurs with Coates-Claisen rearrangement is established. This synthetic strategy enabled the rapid assembly of enantiomerically enriched δ-hydroxychromenone-derived esters/amides under mild conditions with good to excellent yields and broad substrate scope.

Platinum-Catalyzed α,β-Desaturation of Cyclic Ketones through Direct Metal–Enolate Formation

The development of a platinum-catalyzed desaturation of cyclic ketones to their conjugated α,β-unsaturated counterparts is reported in this full article. A unique diene-platinum complex was identified to be an efficient catalyst, which enables direct metal-enolate formation. The reaction operates under mild conditions without using strong bases or acids. Good to excellent yields can be achieved for diverse and complex scaffolds. A wide range of functional groups, including those sensitive to acids, bases/nucleophiles, or palladium species, are tolerated, which represents a distinct feature from other known desaturation methods. Mechanistically, this platinum catalysis exhibits a fast and reversible α-deprotonation followed by a rate-determining β-hydrogen elimination process, which is different from the prior Pd-catalyzed desaturation method. Promising preliminary enantioselective desaturation using a chiral-diene-platinum complex has also been obtained.

CeO2-Supported Pd(II)-on-Au Nanoparticle Catalyst for Aerobic Selective α,β-Desaturation of Carbonyl Compounds Applicable to Cyclohexanones

Direct selective desaturation of carbonyl compounds to synthesize α,β-unsaturated carbonyl compounds represents an environmentally benign alternative to classical stepwise procedures. In this study, we designed an ideal CeO2-supported Pd(II)-on-Au nanoparticle catalyst (Pd/Au/CeO2) and successfully achieved heterogeneously catalyzed selective desaturation of cyclohexanones to cyclohexenones using O2 in air as the oxidant. Besides cyclohexenones, various bioactive enones can also be synthesized from the corresponding saturated ketones under open air conditions in the presence of Pd/Au/CeO2. Preliminary mechanistic studies revealed that α-C-H bond cleavage in the substrates is the turnover-limiting step of this desaturation reaction.

Substituent-Oriented Synthesis of Substituted Pyrazoles/Chromeno[3,2- c]pyrazoles via Sequential Reactions of Chromones/3-Chlorochromones and Tosylhydrazones

A facile and efficient synthetic strategy for the chemoselective synthesis of monocyclic/tricyclic-fused pyrazoles was developed, and it was oriented by different 3-position substituents (H or Cl) on the chromones. The reaction proceeded in a one-pot sequential way with a broad substrate scope and moderate to excellent yields.

Gold nanoparticles on OMS-2 for heterogeneously catalyzed aerobic oxidative α,β-dehydrogenation of β-heteroatom-substituted ketones

In the presence of Au nanoparticles supported on manganese oxide OMS-2 (Au/OMS-2), various kinds of β-heteroatom-substituted α,β-unsaturated ketones (heteroatom = N, O, S) can be synthesized through α,β-dehydrogenation of the corresponding saturated ketones using O2 (in air) as the oxidant. The catalysis of Au/OMS-2 is truly heterogeneous, and the catalyst can be reused.

Rhodium/chiral diene-catalyzed asymmetric 1,4-addition of arylboronic acids to chromones: A highly enantioselective pathway for accessing chiral flavanones

Chromone has been noted to be one of the most challenging substrates in the asymmetric 1,4-addi-tion of α,β-unsaturated carbonyl compounds. By employing the rhodium complex associated with a chiral diene ligand, (R,R)-Ph-bod, the 1,4-addition of a variety of aryl-boronic acids was realized to give high yields of the corresponding flavanones with excellent enantioselectivities (≥97% ee, 99% ee for most substrates). Ring-opening side products, which would lead to erosion of product enantioselectivity, were not observed under the stated reaction conditions.

Palladium(III)-catalyzed fluorination of arylboronic acid derivatives

A practical, palladium-catalyzed synthesis of aryl fluorides from arylboronic acid derivatives is presented. The reaction is operationally simple and amenable to multigram-scale synthesis. Evaluation of the reaction mechanism suggests a single-electron-transfer pathway, involving a Pd(III) intermediate that has been isolated and characterized.

COMPOUNDS THAT EXPAND HEMATOPOIETIC STEM CELLS

The present invention relates to compounds and compositions for expanding the number of CD34+ cells for transplantation. The invention further relates to a cell population comprising expanded hematopoietic stem cells (HSCs) and its use in autologous or allogeneic transplantation for the treatment of patients with inherited immunodeficient and autoimmune diseases and diverse hematopoietic disorders to reconstitute the hematopoietic cell lineages and immune system defense.