92549-46-7

Usage

Preparation

Preparation by reaction of o-methoxyphenylacetic acid with resorcinol in the presence of boron trifluoride etherate under argon on a water bath for 1 h (98%).

Upstream product

• 7035-03-2 2-methoxy-benzeneacetonitrile 
• 108-46-3 recorcinol 
• 93-25-4 2-methoxyphenylacetic acid 

Downstream Products

• 18440-00-1 2-Hydroxy-4-methoxyphenyl 2-methoxybenzyl ketone 
• 63909-40-0 7-hydroxy-3-(2-methoxyphenyl)-4H-chromen-4-one 
• 323575-75-3 2-ethyl-7-hydroxy-3-(2-methoxyphenyl)chromen-4-one 
• 637748-34-6 3-(2-methoxyphenyl)-4-oxo-2-trifluoromethyl-4H-chromen-7-yl cyclopropanecarboxylate 
• 637753-03-8 3-(2-methoxyphenyl)-4-oxo-4H-chromen-7-yl diethylcarbamate 
• 19725-40-7 7-methoxy-3-(2-methoxyphenyl)-4H-chromen-4-one 
• 855624-01-0 2-hydroxy-7-methoxy-3-(2-methoxy-phenyl)-chroman-4-one 
• 308087-55-0 7-hydroxy-3-(2-methoxy-phenyl)-2-methyl-chromen-4-one 
• 1081127-17-4 C₁₅H₁₃NO₃ 

Relevant academic research and scientific papers

Enantioselective Synthesis of Isoflavanones and Pterocarpans through a RuII-Catalyzed ATH-DKR of Isoflavones

Noyori-Ikariya RuII complexes promoted the one-pot C=C/C=O bonds reduction of isoflavones using sodium formate as the hydrogen source through Asymmetric Transfer Hydrogenation-Dynamic Kinetic Resolution (ATH-DKR). Due to the neutral conditions employed, isoflavones with different substituents at the 2’-position of B-ring (H, OH, OMe and Br) were successfully reduced. Ten cis-3-phenylchroman-4-ols were selectively obtained (>20 : 1 dr) in good yields (up to 86 %) and excellent enantioselectivities (up to >99 : 1 er). The synthetic applications of these chiral compounds were also demonstrated. Enantioenriched isoflavanones were obtained under mild metal-free oxidation of the cis-3-phenylchroman-4-ols while pterocarpans were synthesized by two strategies: an acid-catalyzed cyclization and a novel approach based on a Pd-catalyzed C?O intramolecular cross-coupling reaction.

A Concise Approach to Oxo-Dehydrorotenoid by Direct Lactonization and the Total Syntheses of Stemonone, Rotenonone, 6-Oxo-dehydroelliptone, and 6-Oxo-6a,12a-dehydrodeguelin

An approach to construct the oxo-dehydrorotenoids via direct lactonization of isoflavone-2-carboxylic acids is reported. The present reaction proceeds smoothly with good substrate scope and an operationally simple protocol. The application of this method

Development of 3-alkyl-6-methoxy-7-hydroxy-chromones (AMHCs) from natural isoflavones, a new class of fluorescent scaffolds for biological imaging

Starting from 7-hydroxyisoflavones, we developed a new class of fluorescent scaffolds, 3-alkyl-6-methoxy-7-hydroxy-chromones (AMHCs, MW ～ 205.19, λab ～ 350 nm, λem ～ 450 nm) via a trial and error process. AMHCs have the advantages of being a small molecular moiety, having strong fluorescence in basic buffers, reasonable solubility and stability, non-toxicity, and are conveniently linked to pharmacophores. AMHCs were successfully used in fluorescence microscopy imaging of cells and tissues. This journal is

Synthesis and Aminomethylation of 3-Substituted 6-Hydroxy-1,2-Benzisoxazoles

Oximes of 2,4-dihydroxybenzophenones, 1-(2,4-dihydroxyphenyl)-2-phenylethanones, and 1-(2,4-di-hydroxyphenyl)-2-phenoxyethanones were dehydrated with 1,1'-carbonyldiimidazole, yielding 3-substi-tuted 6-hydroxy-1,2-benzisoxazoles, aminomethylation reactions of which were studied with various reagents.

Synthesis, optical resolution, absolute configuration, and osteogenic activity of cis-pterocarpans

A convenient synthesis of natural and synthetic pterocarpans was achieved in three steps. Optical resolution of the respective enantiomers was accomplished by analytical and semi-preparative HPLC on a chiral stationary phase. For medicarpin and its synthetic derivative 9-demethoxymedicarpin, the absolute configuration was confirmed by a combination of experimental LC-ECD coupling and quantum-chemical ECD calculations. (-)-Medicarpin and (-)-9-demethoxymedicarpin are both 6aR,11aR-configured, and consequently the corresponding enantiomers, (+)-medicarpin and (+)-9-demethoxymedicarpin, possess the 6aS,11aS-configuration. A comparative mechanism study for osteogenic (bone forming) activity of medicarpin (racemic versus enantiomerically pure material) revealed that (+)-(6aS,11aS)-medicarpin (6a) significantly increased the bone morphogenetic protein-2 (BMP2) expression and the level of the bone-specific transcription factor Runx-2 mRNA, while the effect was opposite for the other enantiomer, (-)-(6aR,11aR)-medicarpin (6a), and for the racemate, (±)-medicarpin, the combined effect of both the enantiomers on transcription levels was observed. The Royal Society of Chemistry 2012.

Synthesis and structure-activity relationship study of deoxybenzoins on relaxing effects of porcine coronary artery

Deoxybenzoins are potent antioxidants and tyrosinase inhibitors with potential to be developed as food preservatives and cosmetic ingredients. To explore the potential in cardiovascular protection, 25 polyphenolic deoxybenzoins were synthesized and evaluated for inhibitory effects on KCl-induced porcine coronary arterial contraction. The results revealed deoxybenzoins are significant inhibitors of KCl-induced arterial contraction. Among those synthesized, two-thirds of the deoxybenzoins exhibited moderate to good efficacy on relaxing contracted artery including 2,4-dihydroxydeoxybenzoin with EC50 = 3.30 μM (Emax = 100%, n = 7) and 2,4-dihydroxy-4′-methoxydeoxybenzoin EC50 = 3.70 μM (E max = 100%, n = 5). Deoxybenzoins displayed an endothelium-dependent relaxing manner on the contracted artery; the contractile responses of neither endothelium denuded nor L-NAME deactivated rings were inhibited. The structure-activity relationships of deoxybenzoin on arterial relaxing effects concluded that the 2,4-dihydroxylated deoxybenzoins presented a potential vascular relaxing pharmacophore, with favoring substitution on ring B in the order of H ≤ p-OMe > p-OH > o-OMe > m,p-diOMe ≤ m-OMe.

Expedient Synthesis of Polyhydroxyisoflavones

A general and direct synthesis of polyhydroxy isoflavones (3-phenyl-4H-1-benzopyran-4-ones) starting from the corresponding unprotected phenols and arylacetic acids is described.The aryl rings may carry additional alkyl, methoxy and/or halogeno groups.Intermediate polyhydroxydeoxybenzoins (1,2-diphenylethanones) can also be isolated in good yields.