16982-86-8

Basic information

• Product Name: 2,3-Dihydro-3-methyl-4H-1-benzopyran-4-one
• Synonyms: 2,3-Dihydro-3-methyl-4H-1-benzopyran-4-one;3-methylchroman-4-one;3-METHYL-3,4-DIHYDRO-2H-1-BENZOPYRAN-4-ONE
• CAS NO: 16982-86-8
• Molecular Formula: C₁₀H₁₀O₂
• Molecular Weight: 162.19
• Mol File: 16982-86-8.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2,3-Dihydro-3-methyl-4H-1-benzopyran-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-Dihydro-3-methyl-4H-1-benzopyran-4-one(16982-86-8)
• EPA Substance Registry System: 2,3-Dihydro-3-methyl-4H-1-benzopyran-4-one(16982-86-8)

Safety Data

• Hazardous Substances Data: 16982-86-8(Hazardous Substances Data)

Upstream product

• 491-37-2 2,3-dihydro-4H-1-benzopyran-4-one 
• 74-88-4 methyl iodide 
• 122080-54-0 Se-phenyl 2-(allyloxy)selenobenzoate 
• 104416-44-6 3-Hydroxy-2-methyl-1-(o-hydroxyphenyl)-1-propanone 
• 139449-29-9 3-methyl-3-(phenylsulfonyl)chroman-4-one 
• 52542-42-4 2-allyloxybenzoyl chloride 
• 121-44-8 triethylamine 
• 544-92-3 copper(I) cyanide 
• 108-98-5 thiophenol 
• 646064-56-4 ethyl 2-methyl-3-phenoxypropanoate 
• 28752-82-1 2-(allyloxy)benzaldehyde 
• 79-41-4 poly(methacrylic acid) 
• 88284-48-4 2-(trimethylsilyl)phenyl trifluoromethanesulfonate 
• 24454-24-8 3-methylchroman-4-ol 

Downstream Products

• 646064-64-4 3-benzyloxycarbonyl-3-methylchroman-4-one 
• 85-90-5 3-methylchromone 

Relevant articles and documents

NOVEL COMPOUNDS

The invention relates to compounds of formula (I) and related aspects.

NOVEL COMPOUNDS

The invention relates to compounds of formula (I): and related aspects.

Relay Catalysis by Achiral Borane and Chiral Phosphoric Acid in the Metal-Free Asymmetric Hydrogenation of Chromones

A strategy of relay catalysis by achiral borane and chiral phosphoric acid was successfully developed for the asymmetric hydrogenation of chromones, giving the desired products in high yields with up to 95% ee. Achiral borane and chiral phosphoric acid are highly compatible in this reaction. The achiral borane acts as a Lewis acid for the first-step hydrogenation, and the chiral phosphoric acid acts as an effective chiral proton shuttle to control the enantioselectivity.

Oxidant-Free Selective Synthesis of Functionalized Chroman-4-ones from ortho -Hydroxyacetophenones under HOAc/DMSO Conditions

A metal-free and oxidant-free acid-promoted DMSO activation and subsequent reaction is reported. In this protocol, two molecules of DMSO are activated by HOAc and serve as dual synthons which react with ortho-hydroxyacetophenones, affording 3-(methylthiomethyl)chroman-4-ones in moderate to good yields with high selectivity.

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.

Cobalt-catalyzed cyclization with the introduction of cyano, acyl and aminoalkyl groups

An efficient synthesis of carbo-and heterocycles using CC, CO and CN bonds under cobalt catalysis is described. The substituents on olefins are key for controlling the regio-and chemoselectivity in the initial hydrogen atom transfer step and quaternary carbons are efficiently constructed under mild conditions. Cyclopropane cleavage and tandem cyclization give highly functionalized bicyclic skeletons in a single operation.

Generation of Phosphoranyl Radicals via Photoredox Catalysis Enables Voltage-Independent Activation of Strong C-O Bonds

Despite the prevalence of alcohols and carboxylic acids as functional groups in organic molecules and the potential to serve as radical precursors, C-O bonds remain difficult to activate. We report a synthetic strategy for direct access to both alkyl and acyl radicals from these ubiquitous functional groups via photoredox catalysis. This method exploits the unique reactivity of phosphoranyl radicals, generated from a polar/SET crossover between a phosphine radical cation and an oxygen-centered nucleophile. We show the desired reactivity in the reduction of benzylic alcohols to the corresponding benzyl radicals with terminal H atom trapping to afford the deoxygenated products. Using the same method, we demonstrate access to synthetically versatile acyl radicals, which enables the reduction of aromatic and aliphatic carboxylic acids to the corresponding aldehydes with exceptional chemoselectivity. This protocol also transforms carboxylic acids to heterocycles and cyclic ketones via intramolecular acyl radical cyclizations to forge C-O, C-N, and C-C bonds in a single step.

Straightforward synthesis of functionalized chroman-4-ones through cascade radical cyclization-coupling of 2-(allyloxy)arylaldehydes

A novel and direct approach to synthesize a series of phosphonate, azide and hydroxy functionalized chroman-4-ones has been developed. The cascade transformation appears to proceed through an intramolecular addition of an in situ generated acyl radical onto the alkene, followed by a selective nucleophilic radical-electrophilic radical cross coupling.

Development of a chiral bis(guanidino)iminophosphorane as an uncharged organosuperbase for the enantioselective amination of ketones

Chiral bis(guanidino)iminophosphoranes were designed and synthesized as chiral uncharged organosuperbase catalysts that facilitate activation of less-acidic pro-nucleophiles. The newly developed bis(guanidino) iminophosphoranes, which possess the highest basicity among chiral organocatalysts reported to date, were proven to be a superb class of chiral organosuperbases by reaction of azodicarboxylates with 2-alkyltetralones and their analogues as the less acidic pro-nucleophiles.

Metal-free desulfonylation reaction through visible-light photoredox catalysis

The desulfonylation of β-arylketosulfones has been achieved in good to excellent yields by using 3-W blue LEDs light, 1 mol-% organic dye eosin Y bis(tetrabutylammonium salt) as photocatalyst, and diisopropylethylamine as reducing agent. Mechanistic studies demonstrate that oxidative quenching of the excited eosin Y by β-arylketosulfones plays a crucial role in the present photoredox catalytic cycle. Reductive desulfonylation is essential to enable to use of a sulfone as an auxiliary group. For reductive removal of sulfones, highly aggressive metal-containing reducing agents and harsh reaction conditions are often employed. In this paper, metal-free desulfonylation of β-arylketosulfones can be achieved efficiently at room temperature under visible-light irradiation.