615-06-5

Usage

Uses

Used in Research Applications:
Methyl 3-(2-furyl)-3-oxo-propanoate is used as a research chemical for [application reason], given its unique structure and properties. methyl 3-(2-furyl)-3-oxo-propanoate's carbonyl, ester, and furan ring components make it a potential candidate for various chemical reactions and studies in the field of organic chemistry.
Used in Pharmaceutical Research:
In the pharmaceutical industry, methyl 3-(2-furyl)-3-oxo-propanoate is used as a starting material or intermediate in the synthesis of complex molecules for drug development. Its structural features may contribute to the creation of novel compounds with potential therapeutic applications.
Used in Material Science:
Methyl 3-(2-furyl)-3-oxo-propanoate is used as a component in the development of new materials, such as polymers or composites, due to its reactive functional groups. Its incorporation into these materials could lead to enhanced properties, such as improved thermal stability or chemical resistance.

InChI:InChI=1/C8H8O4/c1-11-8(10)5-6(9)7-3-2-4-12-7/h2-4H,5H2,1H3

Upstream product

• 98-01-1 furfural 
• 6832-16-2 methyl diazoacetate 
• 67-56-1 methanol 
• 78078-05-4 1-Furan-2-yl-3,3-bis-methylsulfanyl-propenone 
• 1192-62-7 1-(2-furyl)-1-ethanone 
• 616-38-6 carbonic acid dimethyl ester 
• 527-69-5 2-furancarbonyl chloride 
• 79-20-9 acetic acid methyl ester 
• 88-14-2 2-furanoic acid 
• 38330-80-2 monomethyl monopotassium malonate 
• 2979-48-8 1-(2-furoyl)-imidazole 
• 16695-14-0 Malonic acid monomethyl ester 
• 2414-98-4 magnesium ethylate 
• 614-99-3 Ethyl 2-furoate 

Downstream Products

• 1047643-55-9 N-[2-(2,4-dichloro-phenoxy)-ethyl]-3-furan-2-yl-3-oxo-propionamide 
• 1425865-27-5 C₁₇H₁₁N₃O₃ 
• 1776055-05-0 (4-(5-(furan-2-yl)-2-phenylpyrazolo[1,5-a]pyrimidin-7-yl)piperazin-1-yl)(furan-3-yl)methanone 
• 6836-83-5 5-furan-2-yl-2-phenyl-1,2-dihydro-pyrazol-3-one 
• 1453112-06-5 C₁₄H₁₆O₂ 
• 95127-17-6 methyl 2-benzyl-3-(furan-2-yl)propanoate 
• 1453112-05-4 C₁₅H₁₄O₃ 

Relevant academic research and scientific papers

Enantio-differentiating hydrogenation of methyl 2-furoylacetate and its analogs over tartaric acid-modified Raney nickel

Hydrogenation of methyl 2-furoylacetate over TA-MRNi reduced the three unsaturated bonds to give methyl tetrahydro-2-furoylacetate, the enantiomeric excess (ee) of which at the 3-position was 77%, whereas the 4-position was racemic. Under the same conditions, the substrate of 4-methoxycarbonyl analogue was resulted in hydrogenation of only the ketone moiety to give the corresponding chiral sec-alcohol having a furan ring in 69% ee.

A three-step synthesis of the guaianolide ring system

By using a gallium(III) triflate catalyzed intramolecular (4+3) cycloaddition, a few functionalized furan-derived tricycles that share the common guaianolide sesquiterpene ring system were prepared in a stereoselective manner in only three steps from commercially available starting materials. A discussion of the formation of alternative products is included, with possible substrate requirements to achieve the key cycloaddition step in an efficient way. Copyright

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.

Access to pyridines via cascade nucleophilic addition reaction of 1,2,3-triazines with activated ketones or acetonitriles

We studied the cascade nucleophilic addition reactions of 1,2,3-triazines with activated acetonitriles or ketones, which were used to construct highly substituted pyridines that are not easily accessed by conventional methods. The strategy addressed some structural diversity issues currently facing medicinal chemistry, and the resulting pyridines could be used as convenient precursors for the synthesis of related pharmaceuticals. In particular, our method was applied to the syntheses of the marketed drug etoricoxib and several biologically important molecules in a few steps.

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.

Quinone-Fused Pyrazoles through 1,3-Dipolar Cycloadditions: Synthesis of Tricyclic Scaffolds and in vitro Cytotoxic Activity Evaluation on Glioblastoma Cancer Cells

A novel and straightforward synthesis of highly substituted isoquinoline-5,8-dione fused tricyclic pyrazoles is reported. The key step of the synthetic sequence is a regioselective, Ag2CO3 promoted, 1,3-dipolar cycloaddition of C-heteroaryl-N-aryl nitrilimines and substituted isoquinoline-5,8-diones. The broad functional group tolerability and mild reaction conditions were found to be suitable for the preparation of a small library of compounds. These scaffolds were designed to interact with multiple biological residues, and two of them, after brief synthetic elaborations, were analyzed by molecular docking studies as potential anticancer drugs. In vitro studies confirmed the potent anticancer effects, showing promising IC50 values as low as 2.5 μm against three different glioblastoma cell lines. Their cytotoxic activity was finally positively correlated to their ability to inhibit PI3K/mTOR kinases, which are responsible for the regulation of diverse cellular processes in human cancer cells.

Nickel-catalyzed enantioselective hydrogenation of β-(acylamino)acrylates: Synthesis of chiral β-amino acid derivatives

The nickel-catalyzed asymmetric hydrogenation of β-(acylamino)acrylates has been developed, affording chiral β-amino acid derivatives with excellent yields (95-99% yield) and enantioselectivities (97-99% ee). With the Ni-Binapine system, high enantioselectivities (98-99% ee) have also been obtained in the hydrogenation of Z/E isomeric mixtures of β-alkyl and β-aryl β-(acylamino)acrylates. The synthesis of chiral β-amino acid derivatives on a gram scale has also been achieved with 0.2 mol % catalyst loading.

Oxidative Coupling of Enamines and Disulfides via Tetrabutylammonium Iodide/tert-Butyl Hydroperoxide-Mediated Intermolecular Oxidative C(sp2) S Bond Formation Under Transition Metal-Free Conditions

The reaction of enamine compounds with disulfides in the presence of tert-butyl hydroperoxide and a catalytic amount of tetrabutylammonium iodide conveniently afforded a variety of α-thioenamine compounds through the intermolecular oxidative C(sp2) S coupling. Incorporating both of the sulfide moieties in the disulfides into the final products under oxidative conditions, this novel approach exhibits the feature of atom efficiency. A radical mechanistic pathway for the reaction process has been proposed. (Figure presented.) .

Trimethylchlorosilane-Mediated Mild α-Chlorination of 1,3-Dicarbonyl Compounds Promoted by Phenyliodonium Diacetate

Trimethylchlorosilane was used as chlorine source for the α-chlorination of 1,3-dicarbonyl compounds with phenyliodonium diacetate as oxidant at room temperature. The reaction allows the selective synthesis of α-monochlorinated products from different kinds of 1,3-dicarbonyl compounds in good yield. The potential possibility of this conversion for bromination has also been investigated.