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Usage

Uses

Used in Cosmetic Industry:
3-(3-Methoxy-phenyl)-3-oxo-propionic acid methyl ester is used as a fragrance and flavoring agent for its pleasant aroma and taste, enhancing the sensory experience of cosmetic products.
Used in Food Industry:
In the food industry, 3-(3-Methoxy-phenyl)-3-oxo-propionic acid methyl ester is used as a flavoring agent to impart a vanilla-like flavor to various food products, improving their taste and appeal.
Used in Pharmaceutical Synthesis:
3-(3-Methoxy-phenyl)-3-oxo-propionic acid methyl ester is utilized in the synthesis of pharmaceuticals, serving as a key intermediate in the production of various medicinal compounds.
Used in Organic Synthesis:
3-(3-METHOXY-PHENYL)-3-OXO-PROPIONIC ACID METHYL ESTER is also used in the field of organic synthesis, where it serves as a versatile building block for the creation of a wide range of chemical compounds with diverse applications.

InChI:InChI=1/C11H12O4/c1-14-9-5-3-4-8(6-9)10(12)7-11(13)15-2/h3-6H,7H2,1-2H3

Upstream product

• 79-20-9 acetic acid methyl ester 
• 5368-81-0 methyl 3-methoxybenzoate 
• 1711-05-3 m-anisoyl chloride 
• 105-45-3 acetoacetic acid methyl ester 
• 616-38-6 carbonic acid dimethyl ester 
• 586-37-8 1-(3-Methoxyphenyl)ethanone 
• 57570-85-1 lithium enolate of methyl acetate 
• 586-38-9 3-Methoxybenzoic acid 

Downstream Products

• 586-37-8 1-(3-Methoxyphenyl)ethanone 
• 1170144-67-8 C₁₆H₁₈O₄ 
• 886494-11-7 C₁₀H₁₀N₂O₂ 
• 1242162-63-5 methyl 2-(3-methoxybenzoyl)pent-4-ynoate 
• 51699-39-9 ethyl β-(3-methoxyphenyl)-β-hydroxypropionate 
• 72719-08-5 methyl 3-(3-methoxyphenyl)-3-hydroxypropanoate 
• 51699-44-6 1-(3-methoxyphenyl)propane-1,3-diol 
• 1454691-21-4 methyl 3-(acetyloxy)-3-(3-methoxyphenyl)propanoate 
• 1454691-30-5 (R)-(+)-methyl 3-(acetyloxy)-3-(3-methoxyphenyl)propanoate 
• 51699-51-5 3-(3-methoxyphenyl)-3-hydroxypropyl 4-methylbenzenesulfonate 
• 1621176-47-3 1-(3-methoxyphenyl)-3-(4,5,6,7-tetrabromo-2H-benzotriazol-2-yl)propan-1-ol 
• 118049-72-2 3-(3-methoxyphenyl)-1-phenyl-1H-pyrazol-5(4H)-one 

Relevant academic research and scientific papers

Chiral Vanadyl(V) Complexes Enable Efficient Asymmetric Reduction of β-Ketoamides: Application toward (S)-Duloxetine

High-valent chiral oxidovanadium(V) complexes derived from 3,5-substituted-N-salicylidene-l-tert-leucine were used as catalysts in asymmetric reduction of N-benzyl-β-ketoamides. Among six different solvents, three different alcohol additives, and two different boranes examined, the use of pinacolborane in tetrahydrofuran (THF) with a t-BuOH additive led to the best results at -20 °C. The corresponding β-hydroxyamides can be furnished with yields up to 92percent and an enantiomeric excess (ee) up to 99percent. We have successfully extended this catalytic protocol for the synthesis of an (S)-duloxetine precursor.

Noncanonical cation-π cyclizations of alkylidene β-ketoesters: Synthesis of spiro-fused and bridged bicyclic ring systems

Three cation-π cyclization cascades initiated at alkylidene β-ketoesters bearing pendent alkenes are described. Depending upon the alkene substitution pattern and the reaction conditions employed, it is possible to achieve selective synthesis of the three different types of products, including 1-halo-3-carbomethoxycyclohexanes, spiro-fused tricyclic systems, and [4.3.1] bridged bicyclic ring systems. All three reactions begin with 6-endo addition of an olefin to the alkylidene β-ketoester electrophile, followed by one of three different cation capture events.

PhIO/Et3N ? 3HF-Mediated Formation of Fluorinated 2H-Azirines via Domino Fluorination/Azirination Reaction of Enamines

A variety of enamine carboxylic esters and enaminones were converted to the biologically interesting fluorinated 2H-azirines through reactions with PhIF2 generated in situ by PhIO and Et3N ? 3HF in 1,2-dichroloethane, which features the hypervalent iodine reagents-mediated introduction of fluorine atom and formation of the 2H-azirine skeleton under metal-free conditions. The domino reaction is postulated to proceed via a PhIF2-mediated oxidative fluorination and a subsequent azirination of the fluorinated enamine intermediates. (Figure presented.).

Dehydrative Nazarov-type electrocyclizations of alkenyl (hetero)aryl carbinols via calcium catalysis: Access to cyclopenta[b]thiophenes and indene derivatives

A general approach to the understudied cyclopenta[b]thiophenes is reported. The products were directly generated from calcium-catalyzed, dehydrative, Nazarov-type electrocyclizations of alkenyl thienyl carbinols in up to 82% yield. The thienyl carbinols demonstrated good tolerance for aryl and heteroaryl substituents on the alkene. Aryl carbinols were also amenable to the calcium-catalyzed conditions and afforded indene derivatives in good yields. In most cases, the reaction was selective for the thermodynamic alkene isomer; however, substituent effects played a role in determining product outcomes. Mechanistically, the calcium catalyst initiated formation of alkenyl (hetero)aryl carbinyl cations which subsequently underwent a 4π electrocyclization and elimination that is reminiscent of the Nazarov reaction. This transformation is significant for two main reasons: 1) it represents one of the only examples of catalysis for dehydrative, Nazarov-type electrocyclizations in which thiophene was compatible; 2) it allowed for the direct formation of cyclopenta[b]thiophenes while circumventing the need for cyclopenta[b]thiophenones as precursors.

Catalytic Asymmetric Nazarov Cyclization of Heteroaryl Vinyl Ketones through a Crystallographically Defined Chiral Dinuclear Nickel Complex

A Ni(NTf2)2 and tetradentate bisimino-bisquinoline ligand complex catalyzed the enantioselective Nazarov cyclization of heteroaryl vinyl ketones. An X-ray-quality crystal was obtained from a mixture of the Ni complex and the substrat

The guareschi pyridine scaffold as a valuable platform for the identification of selective PI3K inhibitors

A novel series of 4-aryl-3-cyano-2-(3-hydroxyphenyl)-6-morpholino-pyridines have been designed as potential phosphatidylinositol-3-kinase (PI3K) inhibitors. The compounds have been synthesized using the Guareschi reaction to prepare the key 4-aryl- 3-cyano-2,6-dihydroxypyridine intermediate. A different selectivity according to the nature of the aryl group has been observed. Compound 9b is a selective inhibitor against the PI3Kα isoform, maintaining a good inhibitory activity. Docking studies were also performed in order to rationalize its profile of selectivity.

Base initiated aromatization/CO bond formation: A new entry to O-pyrazole polyfluoroarylated ethers

A base initiated intermolecular SNAr reaction of pyrazolones with polyfluoroarenes was developed. The process involved the isomerization aromatization of pyrazolone followed by the CO bond formation via the selective CF bond cleavage. With this strategy, a wide range of O-pyrazole polyfluoroarylated ethers bearing diverse functional groups were synthesized in mild to good yields. Additionally, our method was also applied to the isoxazol substrates.

Rhodium-catalyzed enantioseletive hydrogenation of tetrasubstituted α-acetoxy β-enamido esters: A new approach to chiral α-hydroxyl-β-amino acid derivatives

Asymmetric hydrogenation of tetrasubtitued α-acetoxy β-enamido esters with rhodium catalysts based on chiral diphosphine ligands provides an efficient and concise route to the synthesis of chiral α-hydroxyl-β-amino acid derivatives in excellent enantioselectivities. The products are valuable chiral building blocks in many biologically active compounds and have important applications in organic synthesis.

Studies on the chemoenzymatic synthesis of (R)- and (S)-methyl 3-aryl-3-hydroxypropionates: The influence of toluene-pretreatment of lipase preparations on enantioselective transesterifications

Two series (para- and meta-substituted) of racemic methyl esters of 3-aryl-3-hydroxypropionic acid were prepared after which the enantiomers were separated by an enzyme-catalyzed transesterification. Several lipases were investigated as the catalyst. The influence of the enzyme pretreatment, as well as substrate concentration, reaction temperature, stirring manner, and substrate conversion on the stereochemical outcome of the biotransformation process were investigated in detail. The best results were achieved by using solvent-pretreated lipase from Pseudomonas fluorescens or Burkholderia cepacia suspended in toluene, and vinyl acetate as the acetyl group donor.

HETEROCYCLIC COMPOUNDS FOR THE INHIBITION OF PASK

Disclosed herein are new heterocyclic compounds and compositions and their application as pharmaceuticals for the treatment of disease. Methods of inhibiting PAS Kinase (PASK) activity in a human or animal subject are also provided for the treatment of diseases such as diabetes mellitus.