2040-04-2

Usage

Uses

Used in Pharmaceutical Industry:
2',6'-Dimethoxyacetophenone is used as an intermediate in the synthesis of various pharmaceutical compounds, such as 4-fluororesorcinol. Its role in inhibiting hepatic mixed function oxidases makes it a valuable compound for the development of drugs targeting liver-related conditions.
Used in Research and Development:
The metabolism of 2',6'-dimethoxyacetophenone has been studied, providing insights into its potential applications in the development of new drugs and therapies. This research can contribute to a better understanding of the compound's properties and its interactions with biological systems.

Synthesis Reference(s)

Tetrahedron, 49, p. 10843, 1993 DOI: 10.1016/S0040-4020(01)80238-6

InChI:InChI=1/C10H12O3/c1-7(11)10-8(12-2)5-4-6-9(10)13-3/h4-6H,1-3H3

Upstream product

• 917-64-6 methyl magnesium iodide 
• 16932-49-3 2,6-dimethoxybenzonitrile 
• 699-83-2 2,6-dihydroxylacetophenone 
• 77-78-1 dimethyl sulfate 
• 141-78-6 ethyl acetate 
• 151-10-0 1,3-Dimethoxybenzene 
• 148230-18-6 methyl α-(2,6-dimethoxyphenyl)vinyl ether 
• 108-24-7 acetic anhydride 
• 74-88-4 methyl iodide 
• 1466-76-8 2-6-dimethoxybenzoic acid 
• 75-05-8 acetonitrile 
• 703-23-1 2'-hydroxy-6'-methoxyacetophenone 
• 616-38-6 carbonic acid dimethyl ester 
• 99501-03-8 (±)-1-(2,6-dimethoxyphenyl)ethanol 

Downstream Products

• 25108-61-6 1,3-dimethoxy-2-(1-methylethenyl)benzene 
• 99501-03-8 (±)-1-(2,6-dimethoxyphenyl)ethanol 
• 36335-47-4 2,6-dimethoxy-3-chlorobenzoic acid 
• 1466-76-8 2-6-dimethoxybenzoic acid 
• 31709-82-7 (2,6-dimethoxy-phenyl)-glyoxylic acid 
• 101689-20-7 2,6-Dimethoxyphenylglyoxal 
• 121883-87-2 2-(1,2-Dimethyl-propenyl)-1,3-dimethoxy-benzene 
• 122078-20-0 (1S,1'S)-N-(1'-phenylethyl)-1-(2'',6''-dimethoxyphenyl)ethylamine 
• 128113-81-5 (1R,1'S)-N-(1'-phenylethyl)-1-(2'',6''-dimethoxyphenyl)ethylamine 
• 122078-14-2 [1-(2,6-Dimethoxy-phenyl)-eth-(E)-ylidene]-((S)-1-phenyl-ethyl)-amine 
• 145629-34-1 2',6'-Dimethoxychalcone 
• 148230-18-6 methyl α-(2,6-dimethoxyphenyl)vinyl ether 
• 117379-77-8 (E)-4-(2,6-dimethoxyphenyl)-4-oxo-2-butenoic acid 
• 699-83-2 2,6-dihydroxylacetophenone 

Relevant academic research and scientific papers

Theoretical and experimental investigation of palladium(II)-catalyzed decarboxylative addition of arenecarboxylic acid to nitrile

The reaction mechanism of palladium(II)-catalyzed decarboxylative addition of 2,6-dimethoxybenzoic acid to acetonitrile was investigated by means of density functional theory (DFT) calculations. Calculations of the free energy profile for decarboxylation and carbopalladation indicated carbopalladation as the rate-determining step of the reaction. Investigation of the free energy profile for a series of experimentally evaluated nitrogen-based bidentate palladium ligands revealed that higher energy is required for decarboxylation and carbopalladation employing the experimentally least efficient ligand. The DFT investigation also showed that the relative free energies of the transition states were lowered in polar solvent, and preparative experiments confirmed that a nonoptimal ligand could be greatly improved by addition of water to the reaction system.

Ni-Catalyzed β-Alkylation of Cyclopropanol-Derived Homoenolates

Metal homoenolates are valuable synthetic intermediates which provide access to β-functionalized ketones. In this report, we disclose a Ni-catalyzed β-alkylation reaction of cyclopropanol-derived homoenolates using redox-active N-hydroxyphthalimide (NHPI) esters as the alkylating reagents. The reaction is compatible with 1°, 2°, and 3° NHPI esters. Mechanistic studies imply radical activation of the NHPI ester and 2e β-carbon elimination occurring on the cyclopropanol.

Metal-ligand cooperativity in a ruthenium(II) complex of bis-azoaromatic ligand for catalytic dehydrogenation of alcohols

Herein a new Ru-phosphine complex (1) with molecular formula [RuL(PPh3)Cl2] is reported where L is a redox active pincer ligand 2,6-bis(phenylazo)pyridine. The isolated complex has been characterized by usual spectroscopic techniques including single crystal X-ray crystallographic analysis. Complex 1 efficiently catalyzes aerobic oxidation of a wide range of primary and secondary benzylic, allylic, heterocyclic, alicyclic alcohols under mild conditions and is found to be superior over several other Ru (0, +2 and +3), Ru-H and Ru-PPh3 catalysts. Mechanistic studies indicate that a transient Ru-H intermediate is formed in the catalytic cycle which gets switched into a Ru-hydrazo intermediate via hydrogen-walking mechanism. The catalyst is regenerated by aerial oxidation producing H2O2 as a by-product.

Hydrogen bond donor solvents enabled metal and halogen-free Friedel–Crafts acylations with virtually no waste stream

We have developed a metal and halogen-free Friedel–Crafts acylation protocol with virtually no waste stream generation. We propose a hydrogen bonding donor solvent will form a hydrogen bonding network and may provide significant rate enhancement for Friedel–Crafts reactions. Trifluoroacetic acid is one of the strongest H-bond donor solvents, which is also volatile and can be easily recovered by distillation without need for reaction workup. Our protocol is a ‘green’ Friedel–Crafts acylation process: 1) the catalyst can be recovered and reused; 2) using halogen free starting material (carboxylic acids anhydride or carboxylic acids); 3) no need for aqueous reaction work-up; 4) minimum or no waste steam generation.

Hexafluoro-2-propanol-Promoted Intermolecular Friedel-Crafts Acylation Reaction

The intermolecular Friedel-Crafts acylation was carried out in hexafluoro-2-propanol to yield aryl and heteroaryl ketones at room temperature without any additional reagents.

BORON-CONTAINING SMALL MOLECULES

This invention provides novel compounds of the following formula and pharmaceutical compositions containing such compounds.

1 -HYDROXY-BENZOOXABOROLES AS ANTIPARASITIC AGENTS

Provided are compounds useful for controlling endoparasites both in animals and agriculture. Further provided are methods for controlling endoparasite infestations of an animal by administering an effective amount of a compound as described above, or a pharmaceutically acceptable salt thereof, to an animal, as well as formulations for controlling endoparasite infestations using the compounds described above or an acceptable salt thereof, and an acceptable carrier. The claimed compounds are described by the following Markush formula:A typical example for a compound according to above formula is: A typical example for a compound according to above formula is:

Palladium(II)-catalyzed decarboxylative heck arylations of acyclic electron-rich olefins with internal selectivity

Despite the recent emergence of decarboxylative C-C bond forming reactions, methodologies providing internally arylated electron-rich olefins are still lacking. We herein report on palladium(II)-catalyzed decarboxylative Heck arylations of linear electron-rich olefins with excellent selectivity for the internal position. The method allows a variety of electron-rich linear olefins to undergo arylation with ortho-functionalized aromatic carboxylic acids, including heterocycles. The reaction mechanism has been explored with ESI-MS studies to confirm previous findings, and to reveal the formation of a highly stable palladium complex as a result of the Heck product reacting with the catalyst.

Reactivity switch enabled by counterion: Highly chemoselective dimerization and hydration of terminal alkynes

A counterion-controlled reactivity tuning in Pd-catalyzed highly chemoselective and regioselective dimerization and hydration of terminal alkynes is reported. The use of acetate as counterion favors the formation of an alkenyl alkynyl palladium intermediate which forms hitherto less reported 1,3-diaryl-substituted conjugated enynes after reductive elimination. Using chloride, which is a better leaving group, leads to anion exchange on the alkenylpalladium intermediate with hydroxide which after reductive elimination and tautomerization delivered the hydration products.

An improved palladium(II)-catalyzed method for the synthesis of aryl ketones from aryl carboxylic acids and organonitriles

A palladium(II)-catalyzed decarboxylative protocol for the synthesis of aryl ketones has been developed. The addition of TFA was shown to improve the reaction yield and employing THF as solvent enabled the use of solid nitriles and in only a small excess. Using this method, five different benzoic acids reacted with a wide range of nitriles to produce 29 diverse (hetero)aryl ketone derivatives in up to 94% yield.