158053-33-9

Usage

Uses

Used in Organic Synthesis:
3-NAPHTHALEN-2-YL-3-OXO-PROPIONIC ACID METHYL ESTER serves as a fundamental building block in organic synthesis, contributing to the creation of a variety of complex organic molecules. Its unique structure allows it to be a versatile component in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Research and Development:
In the pharmaceutical industry, 3-NAPHTHALEN-2-YL-3-OXO-PROPIONIC ACID METHYL ESTER is utilized in research and development for its potential applications in medicine. Its biological activities are of interest to scientists who aim to develop new drugs and therapies, making it a valuable compound in the quest for medical advancements.

Upstream product

• 93-09-4 naphthalene-2-carboxylate 
• 616-38-6 carbonic acid dimethyl ester 
• 93-08-3 methyl 2-naphthyl ketone 
• 246140-20-5 methyl dicarbonate 
• 141903-34-6 N-(2'-naphthoyl)imidazole 

Downstream Products

• 824424-57-9 3-(naphthalen-2-yl)-3-oxopropanoic acid 
• 933800-04-5 3-(2,6-dichlorophenyl)-5-naphthalen-2-ylisoxazole-4-methanol 
• 933799-33-8 4-(bromomethyl)-3-(2,6-dichlorophenyl)-5-naphthalen-2-ylisoxazole 
• 933799-46-3 2-chloro-4-[3-(2,6-dichlorophenyl)-5-naphthalen-2-ylisoxazol-4-ylmethoxy]benzaldehyde 
• 933799-68-9 2-chloro-4-[3-(2,6-dichlorophenyl)-5-naphthalen-2-ylisoxazol-4-ylmethoxy]benzoic acid 
• 933799-60-1 methyl 3-((E)-2-{2-chloro-4-[3-(2,6-dichlorophenyl)-5-naphthalen-2-ylisoxazol-4-ylmethoxy]phenyl}vinyl)benzoate 
• 933799-74-7 methyl 3-{2-chloro-4-[3-(2,6-dichlorophenyl)-5-naphthalen-2-ylisoxazol-4-ylmethoxy]benzoylamino}benzoate 

Relevant academic research and scientific papers

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.

Cu-Catalyzed Synthesis of Benzoxazole with Phenol and Cyclic Oxime

A Cu-catalyzed straightforward synthesis of benzoxazoles from free phenols and cyclic oxime esters is reported. The mild reaction conditions tolerate various electron-withdrawing and electron-donating functional groups on both substrates, affording benzoxazoles in moderate to good yields. With this protocol, large-scale syntheses of Ezutromid and Flunoxaprofe in one or two steps are demonstrated. A catalytic mechanism, which includes Cu-catalyzed amination via inner-sphere electron transfer and consequent annulation, is proposed.

Direct Hydrodecarboxylation of Aliphatic Carboxylic Acids: Metal- and Light-Free

A mild and inexpensive method for direct hydrodecarboxylation of aliphatic carboxylic acids has been developed. The reaction does not require metals, light, or catalysts, rendering the protocol operationally simple, easy to scale, and more sustainable. Crucially, no additional H atom source is required in most cases, while a broad substrate scope and functional group tolerance are observed.

Enantioselective decarboxylative Mannich reaction of β-keto acids withC-alkynylN-BocN,O-acetals: access to chiral β-keto propargylamines

The chiral keto-substituted propargylamines are an essential class of multifunctional compounds in the field of organic and pharmaceutical synthesis and have attracted considerable attention, but the related synthetic approaches remain limited. Therefore, a concise and efficient method for the enantioselective synthesis of β-keto propargylaminesviachiral phosphoric acid-catalyzed asymmetric Mannich reaction between β-keto acids andC-alkynylN-BocN,O-acetals as easily availableC-alkynyl imine precursors has been demonstrated here, affording a broad scope of β-ketoN-Boc-propargylamines in high yields (up to 97%) with generally high enantioselectivities (up to 97?:?3 er).

1-cyclohexylpyrazolone carboxylesterase 1 inhibitor as well as preparation and application thereof

The invention discloses a 1-cyclohexylpyrazolone carboxylesterase 1 inhibitor as well as preparation and application thereof. The structural general formula of the carboxylesterase 1 inhibitor is shown in the specification, wherein R1 and R2 are any one of phenyl, benzyl, 2-methylphenyl, 4-methylphenyl, 4-methylbenzyl and 2-naphthyl respectively. The IC50 for preparing hCES1A reaches 50 nanomoles,and the ratio of the IC50 for inhibiting hCES2A to the IC50 for inhibiting hCES1A can reach 252 times. The inhibitor can improve the oral bioavailability of carboxylic ester exogenous prodrugs by inhibiting the activity of human carboxylesterase subtype 1, or can be used as a synergist of clopidogrel, and can also effectively inhibit the generation of fat cell lipid droplets induced by a mouse preadipose 3T3-L1 cell line. According to the carboxylesterase 1 inhibitor, the raw materials are easy to obtain, the cost is low, the synthesis process is simple, and the yield is high; the inhibitionactivity is high, the selectivity is good, and the application prospect is great.

Application of 3-aryl pyrazolone compound in preparation of pancreatic lipase (PL)inhibitor

The invention discloses application of a 3-aryl pyrazolone compound as shown in a formula I in preparation of a pancreatic lipase (PL) inhibitor, and a novel lead compound 23 is found through structural optimization. The 3-aryl pyrazolone compound is used for preparing the PL inhibitor for the first time, the novel lead compound is found accordingly, and a potential choice is provided for developing lipid metabolism regulation target drugs based on the PL.

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.

Cooperative Catalysis with Coupled Chiral Induction in 1,3-Dipolar Cycloadditions of Azomethine Ylides

1,3-Dipolar cycloadditions (1,3-DC) between imino esters (as precursors of N-metallated azomethine ylides) and π-deficient alkenes are promoted by cooperative asymmetric Lewis acid/Br?nsted base catalysis. The components of these catalytic pairs are silver salts derived from enantiopure commercially available BINOL-based phosphoric acids and Cinchona alkaloids. Chiral phosphoric silver(I) salts promote HOMO raising of in situ formed 1,3-dipoles, whereas protonated cinchona alkaloids generate a LUMO lowering for the dipolarophiles resulting in a global acceleration of the 1,3-DC. The best results were obtained with BINOL-derived silver phosphate and hydrocinchonine. Matching between both cooperative metallo- and organocatalyst results in an enhanced enantiomeric excess, superior to that reached by both separate components. NOESY experiments and DFT calculations are compatible with a non-covalent interaction (hydrogen bond) between both catalysts, which results in close contacts and mutually coupled chiral environments.

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.).

Synthesis of trifluoromethylated 2H-azirines through Togni reagent-mediated trifluoromethylation followed by PhIO-mediated azirination

The reaction of enamine compounds with the Togni reagent in the presence of CuI afforded β-trifluoromethylated enamine intermediates, which were converted directly to biologically interesting trifluoromethylated 2H-azirines by an iodosobenzene (PhIO)-mediated intramolecular azirination in a one-pot process.