32140-83-3

Upstream product

• 943-89-5 (E)-3-(4-methoxyphenyl)acrylic acid 
• 108-95-2 phenol 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 91-64-5 coumarin 
• 93340-46-6 (E)-phenyl 3-(4-methoxyphenyl)acrylate 
• 87-66-1 2-hydroxyresorcinol 
• 170456-76-5 4-(4-methoxyphenyl)coumarin 
• 5720-07-0 4-methoxyphenylboronic acid 
• 200055-89-6 4-(4-toluenesulfonyloxy)coumarin 
• 34446-64-5 (E)-3-(4-methoxyphenyl)propenoyl chloride 
• 24393-56-4 ethyl p-methoxycinnamate 
• 100-66-3 methoxybenzene 
• 90-02-8 salicylaldehyde 

Downstream Products

• 943834-07-9 4-(4-hydroxy-phenyl)-chroman-2-one 
• 943834-08-0 4-(4-butoxy-phenyl)-chroman-2-one 

Relevant academic research and scientific papers

Br?nsted acid promoted one-pot synthesis of 4-aryl-3,4-dihydrocoumarins

4-Aryl-3,4-dihydrocoumarins are a class of valuable molecules demonstrating attractive pharmaceutical and biological properties. In this paper, we designed a new and facile approach to synthesis of 4-aryl-3,4-dihydrocoumarin derivatives by Br?nsted acid c

Lewis acid promoted dual bond formation: Facile synthesis of dihydrocoumarins and spiro-tetracyclic dihydrocoumarins

Lewis acid (FeCl3) mediated dual bond (C-C and C-O) formation for synthesis of 3,4-dihydrocoumarins is presented. This method has successfully delivered a number of dihydrocoumarins containing dense functionalities on the aromatic ring. Significantly, the present method enabled achieving dihydrocoumarins with tertiary as well as quaternary carbon atoms at the benzylic position. Gratifyingly, the novel spiro-tetracyclic lactones have also been dextrously prepared using this process. the Partner Organisations 2014.

TMSOTf-catalyzed intramolecular seleno-arylation of tethered alkenes: A novel method for the solid-phase synthesis of dihydrocoumarins and coumarins

TMSOTf-catalyzed intramolecular seleno-arylation of tethered alkenes was performed using polystyrene-supported succinimidyl selenide as the selenium source. This catalytic process provides an efficient method for the regioselective synthesis of dihydrocoumarins possessing a seleno-functionality, followed by traceless cleavage of selenium linker to provide dihydrocoumarins and coumarins in good yields and purities.

GPR40 AGONISTS

The invention is directed to compounds of Formula (I) useful as GPR40 agonists. Pharmaceutical compositions and methods of treating one or more conditions including, but not limited to, insulin resistance, hyperglycemia, obesity, diabetes such as NIDDM, and other disorders related to lipid metabolism, energy homeostasis, and complications thereof, using compounds of the invention are also described.

Synthesis and biological evaluation of 3-aryl-3-(4-phenoxy)-propionic acid as a novel series of G protein-coupled receptor 40 agonists

High-throughput screening of a subset of the J&J compound library containing the carboxylic acid functional group uncovered a bromophenyl derivative as a moderate potent GPR40 agonist. Chemical elaboration of this bromophenyl led to the discovery of a novel series of GPR40 agonists with submicromolar potency. Among them, 22 and 24 behaved as full agonists when compared to the endogenous GPR40 ligand linolenic acid in a functional Ca +2 flux assay in HEK cells expressing GPR40 receptor. Several GPR40 agonists have also demonstrated the ability to induce glucose-mediated insulin secretion in the mouse MIN6 pancreatic β-cell line. Our data supports the hypothesis that GPR40 may play an important role in fatty acid-mediated glucose-dependent insulin secretion. Compound 22 exhibited good pharmacokinetic profile in rat and may serve as a good candidate for in vivo study and may help to determine if GPR40 agonists would be beneficial in the treatment of type II diabetes.

p-Toluenesulfonic acid mediated hydroarylation of cinnamic acids with anisoles and phenols under metal and solvent-free conditions

Hydroarylation of cinnamic acids with anisoles and phenols mediated by p-toluenesulfonic acid (p-TSA) under metal and solvent-free conditions gave 3-(4-methoxyphenyl)-3-phenylpropanoic acids and dihydrocoumarins, respectively, in high yields and excellent selectivity.

The reactions of phenols with α,β-unsaturated aromatic acids in presence of polyphosphoric acid: Synthetic and mechanistic studies

The reactions of cinnamic acid with phenol itself, catechol, hydroquinone, pyrogallol and 2-naphthol in presence PPA were studied and that with resorcinol was reinvestigated. With phenol itself and hydroquinone were obtained 3,4-dihydro-4-phenylcoumarin (1r) and 6-hydroxy-3,4-dihydro-4-phenylcoumarin (1s), respectively, as the sole products. Catechol and pyrogallol, on the other hand, afforded, besides the corresponding 3,4-dihydrocoumarins, viz. 8-hydroxy-3,4-dihydro-4-phenylcoumarin (1t) and 7,8-dihydroxy-3,4-dihydro-4-phenylcoumarin (1u), as the major products, 5,6-dihydroxy-3-phenylindanone (5b) and the chalcone 1-(2′,3′,4′-trihydroxy)-3-phenylpropan-2-en-1-one (3d), respectively, as minor products. But contrary to earlier observation, resorcinol was found to give 7-hydroxy-3,4-dihydro-4-phenylcoumarin (1v) instead of 7-hydroxyflavanone (4e). 2-Naphthol, on the other hand, afforded the chalcone derivative 1-|2′-hydroxynaphthyl|-3-phenylpropan-2-ene-1-one (7) as the exclusive product. The yields of the major products in the above reactions were 50-67% except that with phenol itself yielding 1r in 40% yield. The structures of all the products 1r, 1s, 1t, 1u, 1v, 3d, 5b and 7 were established from their various spectral (IR, 1H and 13C NMR and mass) data. Evidence for plausible mechanisms of formation of the above products was provided.

Highly Efficient and Single Step Synthesis of 4-Phenylcoumarins and 3,4-Dihydro-4-phenylcoumarins over Montmorillonite K-10 Clay, under Microwave Irradiation

A simple, elegant and one-pot synthesis of 3,4-dihydro-4-phenylcoumarins, 4-phenylcoumarins and their derivatives by making use of solid support, montmorillonite K-10 clay in conjunction with microwave irradiation is described.

Palladium in organic synthesis: Part IV-Palladium (0) catalyzed arylation of coumarin

Palladium (0)-catalyzed insertion of bromobenzene and 4-bromoanisole to coumarin affords 3-arylcoumarins (2) and 4-aryl-3,4-dihydrocoumarins (3).