52249-86-2

Usage

Physical state

Pale yellow solid

Usage

Intermediate in the production of pharmaceuticals, agrochemicals, and other organic compounds

Reactivity

Key component in the synthesis of various organic materials

Versatility

Valuable building block for the creation of diverse chemical structures

Functional groups

Contains a benzyl ether functional group and a methoxy-substituted phenyl ring

Applications

Potential use in the development of new drugs and materials, academic research, and industrial processes

InChI:InChI=1/C16H16O3/c1-12(17)15-9-8-14(18-2)10-16(15)19-11-13-6-4-3-5-7-13/h3-10H,11H2,1-2H3

Upstream product

• 552-41-0 1-(2-hydroxy-4-methoxyphenyl)ethanone 
• 100-39-0 benzyl bromide 
• 100-44-7 benzyl chloride 
• 4136-21-4 p-methoxybenzoylmethanol 

Downstream Products

• 15000-00-7 2-(1-hydroxy-1-methyl-ethyl)-4-methoxy-phenol 
• 87487-58-9 (E)-1-(2-Benzyloxy-4-methoxy-phenyl)-3-(3,6-dimethyl-benzofuran-2-yl)-propenone 
• 96755-13-4 1-(2-benzyloxy-4-methoxyphenyl)-3-(6-benzodioxan-1,4-yl)propenone 
• 80378-12-7 1-(2-Benzyloxy-4-methoxyphenyl)-3-(2-methyl-4-thiazolyl)propenone 
• 69470-90-2 (+/-)-1(2-Hydroxy-4-methoxyphenyl)-1-methyl-2-phenyl-ethan 
• 69470-92-4 (+/-)-1(2-Benzyloxy-4-methoxyphenyl)-1-methyl-2-phenyl-ethan 
• 69470-89-9 2-Benzyloxy-4-methoxy-1-((E)-1-methyl-2-phenyl-vinyl)-benzene 
• 823816-52-0 1-(2-(benzyloxy)-4-methoxyphenyl)-2-bromoethan-1-one 
• 209404-16-0 methyl (2-benzyloxy-4-methoxyphenyl)acetate 
• 762275-94-5 1-(2-benzyloxy-5-bromo-4-methoxy-phenyl)-ethanone 
• 77150-91-5 2-benzyloxy-4-methoxyphenylacetylene 
• 166106-01-0 ω-(p-tolyloxy)-2-benzyloxy-4-methoxyacetophenone 
• 166106-02-1 2-benzyloxy-4-methoxy-2'-hydroxy-5'-methyldeoxybenzoin 
• 96754-72-2 (2-Benzyloxy-4-methoxy-phenyl)-[(2S,3R)-3-(2,3-dihydro-benzo[1,4]dioxin-6-yl)-oxiranyl]-methanone 

Relevant academic research and scientific papers

Nickel-Catalyzed Coupling Reaction of α-Bromo-α-fluoroketones with Arylboronic Acids toward the Synthesis of α-Fluoroketones

A nickel-catalyzed coupling reaction of α-bromo-α-fluoroketones with arylboronic acids was reported, which provides an efficient pathway to access 2-fluoro-1,2-diarylethanones in high yields. We also disclosed the synthesis of the monofluorination agents

PYRANOCHROMENYL PHENOL DERIVATIVE, AND PHARMACEUTICAL COMPOSITION FOR TREATING METABOLIC SYNDROME OR INFLAMMATORY DISEASE

Provided are a pyranochromenyl phenol derivative, a pharmaceutically acceptable salt thereof, or a solvate thereof. Also provided is a pharmaceutical composition for preventing or treating metabolic syndrome or inflammatory disease comprising same. The present invention is efficacious in preventing or treating metabolic syndrome or inflammatory disease and is chemically stable.

Total syntheses of (±)-vestitol and bolusanthin III using a wittig strategy

An intramolecular Wittig olefination was utilized to -produce the key isoflav-3-ene intermediate needed to prepare (±)-vestitol and bolusanthin III in ca. 30% and 20% respective yields after eight steps. Georg Thieme Verlag Stuttgart ? New York.

Synthesis of tetracyclic heterocompounds as selective estrogen receptor modulators. Part 1. Process development for scale-up of 2,5,8-substituted 5,11 -dihydrochromeno[4,3-c]chromene derivatives

Unsymmetrical benzopyranobenzopyran compounds are novel selective estrogen receptor modulators (SERMs). A reproducible and nonchromatographic process was developed to prepare multihundred gram quantities of 5-(4-(2-(piperidin-1-yl) ethoxy)-phenyl)-5,11-di

Synthesis and structure-activity relationships of novel IKK-β inhibitors. Part 3: Orally active anti-inflammatory agents

A series of 2-amino-3-cyano-4-alkyl-6-(2-hydroxyphenyl)pyridine derivatives was synthesized and evaluated as IκB kinase β (IKK-β) inhibitors. Modification of a novel IKK-β inhibitor 1 (IKK-β IC 50=1500nM, Cell IC50=8000nM) at the 4-p

Substituted 6-phenyl-pyridin-2-ylamines: Selective and potent inhibitors of neuronal nitric oxide synthase

The synthesis and nNOS and eNOS activity of 6-(4-(dimethylaminoalkyl)-/6- (4-(dimethylaminoalkoxy)-5-ethyl-2-methoxyphenyl)-pyridin-2-ylamines and 6-(4-(dimethylaminoalkyl)-/6-(4-(dimethylaminoalkoxy)-2,5-dimethoxyphenyl) -pyridin-2-ylamines 1-8 are described. These compounds are potent inhibitors of the human nNOS isoform.

Synthesis of isoflavonoids. Enantiopure cis- and trans-6a-hydroxypterocarpans and a racemic trans-pterocarpan

Aldol condensation between phenylacetates and benzaldehydes affords 2,3-diaryl-3-hydroxypropanoates which serve as common precursors to both the first racemic trans-pterocarpan and enantiopure cis- and trans-6a-hydroxypterocarpans.

Atropisomerization Barriers of Configurationally Unstable Biaryl Compounds, Useful Substrates for Atroposelective Conversions to Axially Chiral Biaryls

Configurationally unstable biaryl lactones of type (M)-1 ? (P)-1 and ring-opened 2-acyl-2′-hydroxy biaryl compounds of type (M)-4 ? (P)-4 are versatile precursors for the atroposelective preparation of axially chiral biaryls. The activation barriers of their atropisomerization process, which constitutes a fundamental precondition for the dynamic kinetic resolution, were determined by dynamic NMR spectroscopy for rapid processes and by HPLC-monitored racemization of enantiomerically enriched material for smaller interconversion rates. For the lactones, the free activation energies ΔG?298 increase with the steric demand of the substituent R ortho to the biaryl axis in the series H 1/2 ≈ ms) 1/2 ≈ s) 1/2 ≈ min) 1/2 ≈ d). The formally ring-opened 2-acyl-2′-hydroxy biaryls, which interconvert via the lactol isomers 5 as the cyclic (and thus configurationally less stable) intermediates, have a significantly slower atropisomerization rate as a result of the high loss in activation entropy ΔS? as a consequence of the required intermediate ring closure 4 → 5.

Direct synthesis of pterocarpans via aldol condensation of phenylacetates with benzaldehydes

Aldol condensation between phenylacetates and benzaldehydes affords 2,3- diaryl-3-hydroxypropanoates which are convened into pterocarpans via stepwise deprotection and cyclization in moderate to high yields.

A convenient method for the berizylation of chelated phenolic groups :Use of tetra-n-butylammonium iodide as a catalyst

Benzylation of chelated phenolic groups in different classes of polyphenolics 1-5 has been carried out, in quantitative yields efficiently by making use of tetra-n-butylammonium iodide as a catalyst in the presence of benzyl chloride-acetone-potassium carbonate. The procedure for working up the reaction mixture has also been improved by avoiding the step involving steam distillation required for removal of benzyl chloride after the reaction is over.