37803-48-8

Usage

Uses

Used in Pharmaceutical Industry:
Ethanone, 1-(3,4-dimethoxyphenyl)-2-hydroxyis used as a key intermediate in the synthesis of various pharmaceuticals. Its reactivity and the presence of the 3,4-dimethoxyphenyl group enable the development of new drug candidates with potential therapeutic applications.
Used in Agrochemical Industry:
Ethanone, 1-(3,4-dimethoxyphenyl)-2-hydroxyis also utilized in the production of agrochemicals, where its versatility in chemical reactions allows for the creation of novel compounds with pesticidal or herbicidal properties.
Used in Organic Synthesis Research:
Ethanone, 1-(3,4-dimethoxyphenyl)-2-hydroxyserves as a valuable research tool in organic synthesis, enabling chemists to explore new reaction pathways and develop innovative synthetic methods for the preparation of complex organic compounds.
Used in Fine Chemicals Production:
Due to its reactivity and the ability to undergo specific modifications, Ethanone, 1-(3,4-dimethoxyphenyl)-2-hydroxy- is employed in the synthesis of fine chemicals, which are high-purity chemicals used in various industries, including pharmaceuticals, fragrances, and flavors.

Upstream product

• 186581-53-3 diazomethane 
• 18256-48-9 2,4'-dihydroxy-3'-methoxyacetophenone 
• 39561-76-7 α-acetoxy-3,4-dimethoxyacetophenone 
• 6380-23-0 3,4-dimethoxystyrene 
• 29389-04-6 2-(2,6-dimethoxyphenoxy)-1-(3,4-dimethoxyphenyl)ethan-1-one 
• 140455-40-9 1-(3,4-dimethoxyphenyl)-2-phenoxy-1-ethanone 
• 22675-96-3 2-methoxyphenoxy-3',4'-dimethoxyacetophenone 
• 41564-97-0 1,2-bis(3,4-dimethoxyphenyl)-1,3-propanediol 

Downstream Products

• 73220-34-5 3-(dimethylamino)-1-(2-hydroxy-3,4-dimethoxyphenyl)prop-2-en-1-one 
• 37816-21-0 4′,7,8-trimethoxyisoflavone 
• 61243-84-3 C₁₈H₁₆O₆ 
• 1453477-60-5 C₁₈H₁₆N₂O₅ 

Relevant academic research and scientific papers

Formal Synthesis of Indolizidine and Quinolizidine Alkaloids from Vinyl Cyclic Carbonates

Cyclic carbonates have long been considered relatively inert molecules acting as protecting groups in complex multistep synthetic routes. This study shows that a concise, yet modular synthesis of indolizidine and quinolizidine alkaloids can be developed from vinyl-substituted cyclic carbonate (VCC) intermediates. Through a highly stereoselective palladium-catalyzed allylic alkylation reaction, these alkaloid motifs can be assembled in four synthetic and only two column purification steps. The combined results help to further advance functionalized cyclic carbonates as useful and reactive intermediates in natural product synthesis.

Photocatalytic Cleavage of Aryl Ether in Modified Lignin to Non-phenolic Aromatics

Depolymerization of lignin meets the difficulty in cleaving the robust aryl ether bond. Herein, through installing an internal nucleophile in the β-O-4′ linkage, the selective cleavage of aryl ether was realized by the intramolecular substitution on aryl rings affording non-phenolic arylamine products. In particular, nitrogen-modified lignin models and lignin samples were employed to generate the iminyl radical under photocatalytic reduction, which acted as the internal nucleophile inducing aryl migration from O to the N atom. The following hydrolysis released primary arylamines and α-hydroxy ketones. Mechanism studies including electron spin resonance (ESR), fluorescence quenching experiments, and density functional theory (DFT) calculations proved the aryl migration pathway. This method enables access to non-phenolic arylamine products from lignin conversion.

Enantioselective [3 + 2] Cycloaddition Reaction of Ethynylethylene Carbonates with Malononitrile Enabled by Organo/Metal Cooperative Catalysis

The first catalytic asymmetric decarboxylative [3 + 2] cycloaddition reaction of ethynylethylene carbonates with malononitrile has been developed successfully by an organo/copper cooperative system. This strategy led to a series of optically active polysu

Chemoselective oxidant-free dehydrogenation of alcohols in lignin using Cp?Ir catalysts

A remarkably effective method of chemoselective dehydrogenation of alcohols in lignin has been developed with an iridium catalyst. An additional operation of Zn/NH4Cl via a two-step one pot process could further promote the cleavage of the C-O bond in β-O-4 units in lignin. And this reaction system was also applicable to native lignin as the molecular weight of native lignin decreased obviously as detected by gel permeation chromatography (GPC). Additionally, this is the first to date generation of the by-product H2 from native lignin and the by-product was straightforwardly captured by 1-decene. A probable mechanistic pathway was also proposed with the help of density functional theory (DFT) calculations.

Valine amide carbamate derivative containing propargyloxy group and application thereof

The invention relates to a valine amide carbamate derivative containing a propargyloxy group and a pharmaceutically acceptable salt thereof, belonging to the field of botanical bactericides. The valine amide carbamate derivative has a general formula (I) as shown in the specification, and the substituent R in the general formula (I) is as defined in the specification. The invention also relates to a preparation method for the compound as shown in the general formula (I), an intermediate specially prepared for development of the compound and application of the compound to prevention and treatment of plant diseases.

Two-Step, Catalytic C-C Bond Oxidative Cleavage Process Converts Lignin Models and Extracts to Aromatic Acids

We herein report a two-step strategy for oxidative cleavage of lignin C-C bond to aromatic acids and phenols with molecular oxygen as oxidant. In the first step, lignin β-O-4 alcohol was oxidized to β-O-4 ketone over a VOSO4/TEMPO [(2,2,6,6-tetramethylpiperidin-1-yl)oxyl)] catalyst. In the second step, the C-C bond of β-O-4 linkages was selectively cleaved to acids and phenols by oxidation over a Cu/1,10-phenanthroline catalyst. Computational investigations suggested a copper-oxo-bridged dimer was the catalytically active site for hydrogen-abstraction from Cβ-H bond, which was the rate-determining step for the C-C bond cleavage.

SELECTIVE C-O BOND CLEAVAGE OF OXIDIZED LIGNIN AND LIGNIN-TYPE MATERIALS INTO SIMPLE AROMATIC COMPOUNDS

A method to cleave C-C and C-0 bonds in β-Ο-4 linkages in lignin or lignin sub-units is described. The method includes oxidizing at least a portion of secondary benzylic alcohol groups in β-Ο-4 linkages in the lignin or lignin sub-unit to corresponding ketones and then leaving C-0 or C-C bonds in the oxidized lignin or lignin sub-unit by reacting it with an organic carboxylic acid, a salt of an organic carboxylic acids, and/or an ester of an organic carboxylic acids. The method may utilize a metal or metal-containing reagent or proceed without the metal or metal-containing reagent.

Photochemical and enzymatic SET promoted C-C bond cleavage reactions of lignin β-1 model compounds containing varying number of methoxy substituents on their arene rings

Abstract In the current study, 1,2-diarylpropan-1,3-diols, containing varying numbers of methoxy substituents that mimic β-1 type units in lignins, were prepared and subjected to photochemical and enzymatic SET oxidative C-C bond cleavage reactions to explore how product distributions and reactivity profiles depend on the numbers and positions of arene ring methoxy-substituents. For this purpose, product distributions of SET-promoted photochemical reactions of the β-1 model compounds and the characteristics of lignin peroxidase catalyzed bond cleavage reactions of these substances were explored. The results show that both the photochemical and enzymatic reactions, which are known to occur by initial SET to form arylpropanoid cation radicals, generate predominantly aldehydes and β-hydroxyketones through cation radical C1-C2 bond cleavage pathways. In addition, analysis of the relative quantum efficiencies of the SET photochemical processes shows that they do not depend greatly on the numbers and positions of arene ring methoxy substituents of the β-1 model compounds.

A new chiral C1-symmetric NHC-catalyzed addition to α-aryl substituted α,β-disubstituted enals: Enantioselective synthesis of fully functionalized dihydropyranones

The first enantioselective NHC-catalyzed activation of α-aryl substituted α,β-disubstituted unsaturated aldehyde is successfully developed via a highly-active acyl azolium intermediate. The new C1-symmetric biaryl-saturated imidazolium exhibits a superior ability to enable previously unavailable transformation, and the corresponding fully functionalized dihydropyranones are efficiently synthesized in high yields with excellent enantioselectivities. This journal is

Solar photochemical oxidation of alcohols using catalytic hydroquinone and copper nanoparticles under oxygen: Oxidative cleavage of lignin models

Alcohols are converted into to their corresponding carbonyl compounds using catalytic amounts of 1,4-hydroquinone with a copper nanoparticle electron transfer mediator with oxygen as the terminal oxidant in acetone as solvent under visible light irradiation. These conditions employing biorenewable hydroquinone as reagent were developed from initial experiments using stoichiometric amounts of 1,4-benzoquinone as oxidant. A range of benzylic and aliphatic primary and secondary alcohols are oxidized, affording the corresponding aldehydes or ketones in moderate to excellent yields. The methodology is also applicable to the oxidative degradation of lignin model compounds that undergo C-C bond cleavage to give simple aromatic compounds.