19803-06-6

Upstream product

• 150-76-5 4-methoxy-phenol 
• 2632-13-5 2-Bromo-4'-methoxyacetophenone 
• 14385-49-0 8-(4'-methoxyphenoxy)acetophenone 
• 150-19-6 O-methylresorcine 
• 18064-99-8 2-(3-methoxy-phenoxy)-1-phenyl-ethanone 
• 29556-89-6 2-(4-methoxyphenoxy)-1-phenylethan-1-ol 
• 92409-23-9 3-hydroxy-2-(2-methoxyphenoxy)-1-(4-methoxyphenyl)propan-1-one 
• 5000-65-7 2-bromo-3'-methoxyacetophenone 
• 586-37-8 1-(3-Methoxyphenyl)ethanone 
• 19513-80-5 2-(2-methoxyphenoxy)-1-(4-methoxyphenyl)ethan-1-one 

Downstream Products

• 19803-11-3 6-methoxy-2-(4-methoxyphenyl)benzofuran 
• 1613483-66-1 2-(4-methoxyphenoxy)-1-(4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)ethanone 
• 150-76-5 4-methoxy-phenol 
• 7465-88-5 4-methoxy-N-phenylbenzamide 
• 100-09-4 4-methoxybenzoic acid 
• 1877-75-4 2-(4-methoxyphenoxy)acetic acid 
• 100-06-1 1-(4-methoxyphenyl)ethanone 
• 106-51-4 p-benzoquinone 
• 150-19-6 O-methylresorcine 
• 29556-89-6 2-(4-methoxyphenoxy)-1-phenylethan-1-ol 
• 14385-49-0 8-(4'-methoxyphenoxy)acetophenone 

Relevant academic research and scientific papers

NEGATIVE ALLOSTERIC MODULATION OF GLUN3-CONTAINING N-METHYL-D-ASPARTATE RECEPTORS

Disclosed are negative allosteric modulators of GluN3-containing NMDA receptors. In general, these compounds are highly selective for GluN3 (such as GluN3A and/or GluN3B) over GluN1 and/or GluN2. They can function as non-competitive antagonists with activity that is independent of membrane potential, glycine concentration, and extracellular pH. Also disclosed are pharmaceutical formulations of the negative allosteric modulators. These compounds can be used to enhance synaptic function and/or treating a neurological condition or disorder. Exemplary neurological conditions or disorders include, but are not limited to, major mental disorders, conditions that involve basal ganglia or altered dopamine, substance abuse/addiction or predisposition to substance abuse/addiction, pain disorders, developmental delay or situations with impaired learning, memory, and/or cognition, acute neuronal or glial injuries, and circuit disorders.

Cleavage∕cross-coupling strategy for converting β-O-4 linkage lignin model compounds into high valued benzyl amines via dual C–O bond cleavage

Lignin is the most recalcitrant of the three components of lignocellulosic biomass. The strength and stability of the linkages have long been a great challenge for the degradation and valorization of lignin biomass to obtain bio-fuels and commercial chemicals. Up to now, the selective cleavage of C–O linkages of lignin to afford chemicals contains only C, H and O atoms. Our group has developed a cleavage/cross-coupling strategy for converting 4-O-5 linkage lignin model compounds into high value-added compounds. Herein, we present a palladium-catalyzed cleavage/cross-coupling of the β-O-4 lignin model compounds with amines via dual C–O bond cleavage for the preparation of benzyl amine compounds and phenols.

Benzoic acid resin (BAR): a heterogeneous redox organocatalyst for continuous flow synthesis of benzoquinones from β-O-4 lignin models

A polymer-bound organocatalyst for Baeyer-Villiger reaction and phenol oxidation under continuous flow conditions is described for the first time.BARhas revealed two catalytic activities that enabled the generation of a novel approach for the synthesis of benzoquinones from β-O-4 lignin models in a one-pot protocol. High catalytic activities (yields up to 98%), selectivities, recyclability and productivity were achieved.

Cobalt-Catalyzed Reductive C-O Bond Cleavage of Lignin β-O-4 Ketone Models via in Situ Generation of the Cobalt-Boryl Species

An efficient and mild method for reductive C-O bond cleavage of lignin β-O-4 ketone models was developed to afford the corresponding ketones and phenols with PDI-CoCl2 as the precatalyst and diboron reagent as the reductant. The synthetic utility of the methodology was demonstrated by depolymerization of a polymeric model and gram-scale transformation. Mechanistic studies suggested that this transformation involves steps of carbonyl insertion, 1,2-Brook type rearrangement, β-oxygen elimination, and rate-limiting regeneration of the catalytic active Co-B species.

Sulfuryl Fluoride Mediated Synthesis of Amides and Amidines from Ketoximes via Beckmann Rearrangement

A metal-free and redox-neutral method for Beckmann rearrangement employing inexpensive and readily available SO2F2 gas is described. The reported transformation proceeds at ambient temperature and is compatible with a wide range of sterically and electronically diverse aromatic, heteroaromatic, aliphatic and lignin-like oximes providing amides in good to excellent yields. The reaction proceeds through the formation of an imidoyl fluoride intermediate that can also be used for the synthesis of amidines.

Visible-light-induced C-C bond cleavage of lignin model compounds with cyanobenziodoxolone

The catalytic degradation of lignin to value-added chemicals has received considerable attention over the past decade. Photocatalysis provides promising approaches to enable previously inaccessible transformations. However, examples of the visible-light promoted degradation of lignin are still limited. In this work, the visible-light-induced selective C-C bond cleavage of β-O-4 lignin model compounds has been disclosed via β-scission of in situ generated alkoxy radical intermediates. With cyanobenziodoxolone as the oxidant, a variety of substrates could be transformed into aldehydes in moderate to good yields. In addition, unexpected acetal esters which could conveniently furnish formaldehyde and phenols by alcoholysis were observed.

Cleavage of lignin model compounds and ligninox using aqueous oxalic acid

Aqueous oxalic acid cleaves oxidised β-O-4 lignin model compounds by two distinct mechanisms that are dependent on the presence of the hydroxymethyl substituent. Various β-O-4 phenoxyacetophenones that do not contain the hydroxymethyl substituent undergo oxidative cleavage upon exposure to aqueous oxalic acid in the presence of air, likely through concerted ring opening of a dioxetane intermediate to give the corresponding benzoic acid and phenyl formate. Importantly, detrimental side reactions arising from singlet oxygen and hydroperoxy radicals (from both O2 and oxalic acid) are minimal when the cleavage is run under air compared to neat oxygen. When oxidised β-O-4 lignin model compounds bearing the hydroxymethyl group are cleaved by aqueous oxalic acid, the resulting diketone and phenol products arise from a redox neutral cleavage that is analogous to the formic acid-sodium formate mediated lignin cleavage process reported by Stahl. Aqueous oxalic acid also cleaves lignin itself, with oxidised milled wood lignin (MWLox) from Pinus radiata giving a 14% yield of ethyl acetate soluble aromatics with good selectivity for vanillin. Aqueous oxalic acid appears to be a promising lignin cleavage system given the benign, bio-based reagents, absence of metals and organic solvents and a simple extraction procedure that enables oxalic acid recycling.

Copper-catalyzed synthesis of benzanilides from lignin model substrates 2-phenoxyacetophenones under an air atmosphere

The synthesis of chemicals from biomass-derived compounds is an interesting and challenging topic. In this work, using the lignin-derived 2-phenoxyacetophenones as the feedstock we present a novel approach for the synthesis of benzanilides via the reaction of 2-phenoxyacetophenones with anilines catalyzed by CuCl2 in DMSO at 120 °C under an air atmosphere. This approach has wide scope for 2-phenoxyacetophenones and anilines, and various benzanilides accompanied by the corresponding phenols could be obtained in high yields via changing the 2-phenoxyacetophenones and anilines. The reaction mechanism study indicated that the oxidative cleavage of the C-C bond in 2-phenoxyacetophenones and the formation of a C-N bond occurred simultaneously in the reaction process, resulting in the formation of benzanilides together with phenols.

Palladium-catalyzed α-arylation of aryloxyketones for the synthesis of 2,3-Disubstituted benzofurans

A highly efficient palladium-catalyzed α-arylation of aryloxyketones has been developed, allowing for facile installation of various (hetero)aryl groups at C2 position in good to excellent yields. Subsequent cyclodehydration of the resulting α-arylated ar

Three-step synthesis of an array of substituted benzofurans using polymer-supported reagents

An efficient combinatorial route to substituted 3-phenyl-benzofurans, is achieved by the bromination of acetophenones to α-bromoacetophenones by polymer-supported pyridinium bromide perbromide (PSPBP). The subsequent clean substitution of the obtained bromides by phenols using 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD-P) and cyclodehydration of the resulting α-phenoxyacetophenones using Amberlyst 15, affords pure products without the need for any chromatographic purification step.