29679-58-1

Usage

Uses

Used in Pharmaceutical Industry:
2-(3-phenoxyphenyl)propionic acid is used as an anti-inflammatory agent for the treatment of inflammatory diseases in human and mouse models. It modulates melanocortin receptor 3, contributing to its therapeutic effects on inflammation.
As a positive allosteric modulator, Fenoprofen enhances the activity of melanocortin receptor 3, which plays a crucial role in regulating inflammatory responses. This makes it a valuable compound for the development of novel therapeutics targeting various inflammatory conditions.

InChI:InChI=1/C15H14O3/c1-11(15(16)17)12-6-5-9-14(10-12)18-13-7-3-2-4-8-13/h2-11H,1H3,(H,16,17)

Upstream product

• 31469-22-4 1,1-bis(trimethylsilyloxy)prop-1-ene 
• 514826-78-9 2-iodo-1,3-phenylene bis(trifluoromethanesulfonate) 
• 39515-51-0 3-Phenoxybenzaldehyde 
• 124-38-9 carbon dioxide 
• 6876-00-2 3-bromodiphenyl ether 
• 591-50-4 iodobenzene 
• 620-17-7 3-ethylphenol 
• 78427-95-9 1-ethyl-3-phenoxybenzene 
• 63444-54-2 3-ethenylphenyl phenyl ether 
• 41046-67-7 2-iodoresorcinol 
• 108-46-3 recorcinol 
• 32929-75-2 2-(3-phenoxy-phenyl)-propan-1-ol 
• 70986-29-7 C₂₁H₁₇NO₅ 
• 32852-81-6 (3-phenoxyphenyl)acetic acid 

Downstream Products

• 32853-02-4 N-cyclopropylmethyl-2-(3-phenoxyphenyl)propionamide 
• 33028-97-6 (S)-fenoprofen 
• 31879-05-7 (R)-fenoprofen 
• 37785-47-0 (S)-2-(4-Hydroxy-3-phenoxy-phenyl)-propionic acid 
• 37785-47-0 (R)-2-(4-Hydroxy-3-phenoxy-phenyl)-propionic acid 
• 32929-75-2 2-(3-phenoxy-phenyl)-propan-1-ol 
• 1116086-48-6 (R)-fenoprofen di(1-naphthyl)methyl ester 
• 1213788-19-2 (R,S)-N-fenoprofenyl-1,2,4-triazole 
• 139610-52-9 fenoprofenoyl-CoA 1 
• 1315549-03-1 (+/-)-1-(2-(3-phenoxyphenyl)propanoyl)imidazole 
• 2461-34-9 (1R,2S)-1,2-epoxy-3,4-dihydronaphthalene 
• 24825-01-2 (1aR,7bS)-1a,2,3,7b-tetrahydronaphtho[1,2-b]oxirene 

Relevant academic research and scientific papers

Visible-light photoredox-catalyzed selective carboxylation of C(sp3)?F bonds with CO2

It is highly attractive and challenging to utilize carbon dioxide (CO2), because of its inertness, as a nontoxic and sustainable C1 source in the synthesis of valuable compounds. Here, we report a novel selective carboxylation of C(sp3)?F bonds with CO2 via visible-light photoredox catalysis. A variety of mono-, di-, and trifluoroalkylarenes as well as α,α-difluorocarboxylic esters and amides undergo such reactions to give important aryl acetic acids and α-fluorocarboxylic acids, including several drugs and analogs, under mild conditions. Notably, mechanistic studies and DFT calculations demonstrate the dual role of CO2 as an electron carrier and electrophile during this transformation. The fluorinated substrates would undergo single-electron reduction by electron-rich CO2 radical anions, which are generated in situ from CO2 via sequential hydride-transfer reduction and hydrogen-atom-transfer processes. We anticipate our finding to be a starting point for more challenging CO2 utilization with inert substrates, including lignin and other biomass.

Exploration of New Biomass-Derived Solvents: Application to Carboxylation Reactions

A range of hitherto unexplored biomass-derived chemicals have been evaluated as new sustainable solvents for a large variety of CO2-based carboxylation reactions. Known biomass-derived solvents (biosolvents) are also included in the study and the results are compared with commonly used solvents for the reactions. Biosolvents can be efficiently applied in a variety of carboxylation reactions, such as Cu-catalyzed carboxylation of organoboranes and organoboronates, metal-catalyzed hydrocarboxylation, borocarboxylation, and other related reactions. For many of these reactions, the use of biosolvents provides comparable or better yields than the commonly used solvents. The best biosolvents identified are the so far unexplored candidates isosorbide dimethyl ether, acetaldehyde diethyl acetal, rose oxide, and eucalyptol, alongside the known biosolvent 2-methyltetrahydrofuran. This strategy was used for the synthesis of the commercial drugs Fenoprofen and Flurbiprofen.

Synthesis of pharmaceutical drugs from cardanol derived from cashew nut shell liquid

Cardanol from cashew nut shell liquid extracted from cashew nut shells was successfully converted into various useful pharmaceutical drugs, such as norfenefrine, rac-phenylephrine, etilefrine and fenoprofene. 3-Vinylphenol, the key intermediate for the synthesis of these drugs, was synthesised from cardanol by ethenolysis to 3-non-8-enylphenol followed by isomerising ethenolysis. The metathesis reaction worked very well using DCM, but the greener solvent, 2-methyl tetrahydrofuran, also gave very similar results. Hydroxyamination of 3-vinylphenol with an iron porphyrin catalyst afforded norfenefrine in over 70% yield. Methylation and ethylation of norfenefrine afforded rac-phenylephrine and etilefrine respectively. A sequence of C-O coupling, isomerising metathesis and selective methoxycarbonylation afforded fenoprofene in good yield. A comparison of the routes described in this paper with some standard literature syntheses of 3-vinylphenol and of the drug molecules shows significant environmental advantages in terms of precursors, yields, number of steps, conditions and the use of catalysts. The Atom Economy of our processes is generally similar or significantly superior to those of the literature processes mainly because the side products produced during synthesis of 3-vinylphenol (1-octeme, 1,4-cyclohexadiene and propene) are easily separable and of commercial value, especially as they are bio-derived. The E Factor for the production of 2-vinylphenol by our process is also very low compared with those of previously reported syntheses.

Palladium-Catalyzed α-Arylation of Carboxylic Acids and Secondary Amides via a Traceless Protecting Strategy

A novel traceless protecting strategy is presented for the long-standing challenge of conducting the palladium-catalyzed α-arylation of carboxylic aids and secondary amides with aryl halides. Both of the presented coupling processes occur with a variety of carboxylic acids and amides and with a variety of aryl bromides containing a broad range of functional groups, including base-sensitive functionality like acyl, alkoxycarbonyl, nitro, cyano, and even hydroxyl groups. Five commercial drugs were prepared through this method in one step in 81-96% yield. Gram-scale synthesis of medication Naproxen and Flurbiprofen with low palladium loading further highlights the practical value of this method.

Photocarboxylation of Benzylic C-H Bonds

The carboxylation of sp3-hybridized C-H bonds with CO2 is a challenging transformation. Herein, we report a visible-light-mediated carboxylation of benzylic C-H bonds with CO2 into 2-arylpropionic acids under metal-free conditions. Photo-oxidized triisopropylsilanethiol was used as the hydrogen atom transfer catalyst to afford a benzylic radical that accepts an electron from the reduced form of 2,3,4,6-tetra(9H-carbazol-9-yl)-5-(1-phenylethyl)benzonitrile generated in situ. The resulting benzylic carbanion reacts with CO2 to generate the corresponding carboxylic acid after protonation. The reaction proceeded without the addition of any sacrificial electron donor, electron acceptor or stoichiometric additives. Moderate to good yields of the desired products were obtained in a broad substrate scope. Several drugs were successfully synthesized using the novel strategy.

Method for synthesizing arylpropionic acid-like nonsteroidal antiinflammatory agent

The invention discloses a method for synthesizing an arylpropionic acid-like nonsteroidal antiinflammatory agent. The method comprises that an aryl acetonitrile compound as a substrate, an amine borane complex and N, N-dimethylformamide as a solvent undergo a methylation reaction under basic conditions to produce an aryl propionitrile compound, and the aryl propionitrile compound is hydrolyzed under strong basic conditions to form the arylpropionic acid-like nonsteroidal antiinflammatory agent. The method creatively uses the amine borane complex and N, N-dimethylformamide as methylation reagents so that bis-methylation and large toxicity caused by the traditional methylation reagents such as methyl iodide and dimethyl sulfate are avoided. The method is simple and is easy to operate. The arylpropionic acid-like nonsteroidal antiinflammatory agent has a high yield and high purity. Compared with the existing method using a metal catalyst system, the method utilizes anon-metallic system so that the use of transition metals is avoided. The method provides a novel approach for preventing metal residues in synthetic drugs.

Selective aryne formation via Grob fragmentation from the [2+2] cycloadducts of 3-triflyloxyarynes

A chemoselective ring-opening protocol of the formal [2+2] cycloadducts of 3-triflyloxyarynes was developed to generate 2,3-aryne intermediate via Grob fragmentation. A variety of 1,3-di- and 1, 2, 3-trisubstituted arenes could be readily accessed through this [2+2] cycloaddition-2,3-aryne formation sequence. The regioselectivity in these transformations originates from the steric repulsion of the aliphatic chain.

Site-Selective Catalytic Carboxylation of Unsaturated Hydrocarbons with CO2 and Water

A catalytic protocol that reliably predicts and controls the site-selective incorporation of CO2 to a wide range of unsaturated hydrocarbons utilizing water as formal hydride source is described. This platform unlocks an opportunity to catalytically repurpose three abundant, orthogonal feedstocks under mild conditions.

2-ARYL-ZINC-PROPIONATE CATALYST AND PREPARATION METHOD AND USE THEREOF

The present invention belongs to the technical field of chemical catalysts, and particularly relates to a zinc 2-arylpropionate catalyst, a preparation method therefor and use thereof The structural formula of the zinc 2-arylpropionate catalyst of the present invention is one of the following structures. The catalyst can be used for homogeneous catalysis of a 1,2-aryl rearrangement reaction of α-haloarylketal, and especially for synthesis of high yield and environmentally friendly 2-arylpropanonic acid non-steroidal anti-inflammatory analgesic drugs, such as, ibuprofen, ketoprofen, loxoprofen, flurbiprofen, fenoprofen, or naproxen and the like.

Laccase-Mediator System for Alcohol Oxidation to Carbonyls or Carboxylic Acids: Toward a Sustainable Synthesis of Profens

By combining two green and efficient catalysts, such as the commercially available enzyme laccase from Trametes versicolor and the stable free radical 2,2,6,6-tetramethylpiperidine-N-oxyl (TEMPO), the oxidation in water of some primary alcohols to the corresponding carboxylic acids or aldehydes and of selected secondary alcohols to ketones can be accomplished. The range of applicability of bio-oxidation is widened by applying the optimized protocol to the oxidation of enantiomerically pure 2-arylpropanols (profenols) into the corresponding 2-arylpropionic acids (profens), in high yields and with complete retention of configuration.