3385-34-0

Usage

Uses

Used in Organic Synthesis:
5-Carbethoxy-4,6-dimethyl-2-pyrone is used as an intermediate in organic synthesis for the preparation of various compounds. Its unique structure allows it to be a versatile building block for the synthesis of complex organic molecules.
Used in Pharmaceutical Industry:
5-Carbethoxy-4,6-dimethyl-2-pyrone is used as a raw material in the pharmaceutical industry for the development of new drugs. Its chemical properties make it a promising candidate for the synthesis of novel therapeutic agents.
Used in Agrochemicals:
5-Carbethoxy-4,6-dimethyl-2-pyrone is used in the preparation of insect growth regulators with juvenile hormone activity. This application is particularly useful in the development of environmentally friendly pest control solutions.
Used in Bidentate Ligand Synthesis:
5-Carbethoxy-4,6-dimethyl-2-pyrone is used in the synthesis of bidentate ligands, which are important in coordination chemistry and catalysis. These ligands can be used to create new catalysts for various chemical reactions.

InChI:InChI=1/C10H12O4/c1-4-13-10(12)9-6(2)5-8(11)14-7(9)3/h5H,4H2,1-3H3

Upstream product

• 141-97-9 ethyl acetoacetate 
• 1007476-32-5 sodium ethyl acetylacetate enolate 
• 6127-92-0 E-Ethyl β-chlorocrotonate 
• 71-43-2 benzene 
• 1663-67-8 malonoyl dichloride 
• 75-03-6 ethyl iodide 
• 7664-93-9 sulfuric acid 
• 7732-18-5 water 
• 14369-81-4 ethyl 2,3-butadienoate 

Downstream Products

• 86799-57-7 4-Methyl-6-oxo-2-((E)-2-p-tolyl-vinyl)-6H-pyran-3-carboxylic acid 
• 86799-60-2 2-[(E)-2-(4-Chloro-phenyl)-vinyl]-4-methyl-6-oxo-6H-pyran-3-carboxylic acid 
• 86799-59-9 2-[(E)-2-(2-Chloro-phenyl)-vinyl]-4-methyl-6-oxo-6H-pyran-3-carboxylic acid 
• 86799-62-4 4-Methyl-2-[(E)-2-(4-nitro-phenyl)-vinyl]-6-oxo-6H-pyran-3-carboxylic acid 
• 87555-77-9 ethyl trans-2,6-dimethyl-3-(1-methylethyl)-4-(4-morpholino)-3,4-dihydrobenzoate 
• 86799-56-6 4-Methyl-6-oxo-2-((E)-styryl)-6H-pyran-3-carboxylic acid 
• 86799-61-3 2-[(E)-2-(4-Bromo-phenyl)-vinyl]-4-methyl-6-oxo-6H-pyran-3-carboxylic acid 
• 108593-45-9 2,4-Dimethylisophthalsaeure-1-methyl-3-ethylester 
• 108593-46-0 3,5-Dimethylterephthalsaeure-1-methyl-4-ethylester 
• 86799-66-8 4-methyl-6-(4-phenyl-1,3-butadienyl)-2-oxo-2H-pyran-5-carboxylic acid 
• 86799-58-8 2-[(E)-2-(2-Methoxy-phenyl)-vinyl]-4-methyl-6-oxo-6H-pyran-3-carboxylic acid 
• 86799-63-5 2-[(E)-2-(4-Cyano-phenyl)-vinyl]-4-methyl-6-oxo-6H-pyran-3-carboxylic acid 
• 56863-78-6 3,5-Dimethyl-benzene-1,2,4-tricarboxylic acid 4-ethyl ester 1,2-dimethyl ester 
• 87555-76-8 ethyl trans-4-(4-morpholino)-2,3,6-trimethyl-3,4-dihydrobenzoate 

Relevant academic research and scientific papers

Poly substituted 5-functionalized 2-pyrone derivatives: Facile synthesis via tandem nucleophilic addition/lactonization reaction of 1,2-allenyl esters

Polysubstituted 5-functionalized 2-pyrone derivatives were synthesized via the K2CO3-catalyzed reaction of 1,2-allenyl esters and α-substituted ketones with electron-withdrawing groups through a tandem nucleophilic addition/lactonization process. Georg Thieme Verlag Stuttgart.

Catalytic asymmetric tamura cycloadditions

In the presence of a novel, tert-butyl-substituted squaramide-based catalyst, enolizable anhydrides react with alkylidene oxindoles to generate spirooxindole products of significant synthetic interest with excellent enantio- and diastereocontrol. The methodology is of wide scope and encompasses both homophthalic and glutaconic anhydride derivatives, which lead to structurally diverse products. Glutaconic acid-derived anhydrides undergo a clean post-cyclization decarboxylation process which is not a feature of reactions involving homophthalic acid-derived anhydrides. The unusual influence of reaction temperature on diastereocontrol has been probed, with reactions occurring at 30 °C and -30 °C delivering products epimeric at one stereocenter only, in near optical purity. Squared away: The first strategy for bringing about enantioselective Tamura reactions is reported. In the presence of a squaramide-based catalyst, enolizable anhydrides react with alkylidene oxindoles to generate spirooxindole products with excellent enantio- and diastereocontrol. The methodology is of wide scope and leads to structurally diverse products.

Synthesis of some C2-symmetric bidentate ligands and their complexes derived from Feist's acid

Various new C2-symmetric bidentate ligands, bearing phosphorus, nitrogen, and sulfur, were obtained in an efficient manner, starting from (±)-trans-3-methylidenecyclopropane-1,2-dicarboxylic acid (Feist's acid; (±)-trans-3). The structures of the new bidentate ligands, di(tert-butyl) (±)-[(trans-3-methylidenecyclopropane-1,2-diyl)dimethanediyl] biscarbamate ((±)-9), (±)-(trans-3-methyldienecyclopropane-1,2- diyl)dimethanaminium dichloride ((±)-10), (±)-S,S′-[(trans- 3-methylidenecyclopropane-1,2-diyl)dimethanediyl] diethanethioate ((±)-11), and (±)-[(trans-3-methylidenecyclopropane-1,2-diyl) dimethanediyl]bis(diphenylphosphane) ((±)-12), were fully characterized by standard spectroscopic techniques. These new classes of C2- symmetric bidentate ligands have the potential to be used in asymmetric catalysis. Copyright

MECANISMO DE LA REACCION DE COMPUESTOS 1,3-DICARBONILICOS CON ANHIDRIDO TRIFLICO. CICLACION ANOMALA DEL ESTER ACETILACETICO A 3-ETOXICARBONIL-2,6-DIMETIL-4-PIRONA.

The reaction of ethyl acetoacetate (1) with triflic anhydride (Tf2O) in excess, in the presence of nitriles (3) affords 3-ethoxycarbonyl-2,6-dimethyl-4-pyrone (10), instead of 5-ethoxycarbonyl-4,6-dimethyl-2-pyrone (5), which is the usual product formed in the cyclization of 1 catalyzed by protic or Lewis acids.Palabras clave: 2-pirona, 4-pirona, anhidrido triflico, ester acetylacetico.

Extractives from New Zealand Honeys. 5. Aliphatic Dicarboxylic Acids in New Zealand Rewarewa (Knightea excelsa) Honey

Thirty-two aliphatic dicarboxylic acids were identified as methyl esters in the methylated diethyl ether extracts of four unifloral grade New Zealand rewarewa (Knightea excelsa) honeys using combined gas chromatography-mass spectrometry (GC-MS). 2-Methoxybutanedioic acid (O-methylmalic acid) and 4-hydroxy-3-methyl-trans-2-pentenedioic acid are proposed as floral marker substances for New Zealand rewarewa honey.The total level of aliphatic dicarboxylic acids identified in the rewarewa honey samples ranged from 64 to 111 mg/kg, with an average level of 88 mg/kg.Keywords: Rewarewa (Knightea excelsa) honey; aliphatic dicarboxylic acids; 2-methoxybutanedioic acid; 4-hydroxy-3-methyl-trans-2-pentenedioic acid

An improved synthesis of a mixture of diethyl (Z)- and (E)-3-methylglutaconates from ethyl acetoacetate

A simple, efficient two-step synthesis of a mixture of diethyl (Z)- and (E)-3-methylglutaconates from isodehydroacetic acid in 83% yield is described. On the basis of this synthesis an improved procedure for the preparation of a mixture of (Z)- and (E)-3-methylglutaconic acids from ethyl acetoacetate in 44% overall yield was elaborated.

A Stereospecific Synthesis of (+/-)-Abscisic Acid

A convenient separation of (E)- and (Z)-3-methylpent-2-enedioic acids was devised, and it was shown that with acetyl chloride or thionyl chloride the (Z)-acid yields the cyclic anhydride while the (E)-acid forms 6-chloro-4-methylpyran-2-one.The chloropyranone by conventional chemistry gave 4-methyl-6-(2'-oxopropyl)pyran-2-one which condensed with 4-methylpent-3-en-2-one in the presence of pyrrolidine, yielding 4-methyl-6-(2',6',6'-trimethyl-4'-oxocyclohex-2'-enyl)pyran-2-one.Oxidation with selenium dioxide or t-butyl chromate then gave 6-(1'-hydroxy-2',6',6'-trimethyl-4'-oxocyclohex-2'-enyl)-4-methylpyran-2-one, which on reduction by lithium aluminium hydride and reoxidation afforded (+/-)-abscisic acid stereospecifically.

Facile synthesis of anhydromevalonolactone from ethyl acetoacetate

Ethyl acetoacetate was transformed to 3-methylglutaconic anhydride, which upon LAH reduction and Jones oxidation afforded anhydromevalonolactone.

A NEW PYRONE STRATEGY FOR THE SYNTHESIS OF 3-ACYLTETRAMIC ACIDS

The potential of pyrones as precursors to 3-acyltetramic acids has been demonstrated by the conversion of 5-ethoxycarbonyl-4-methoxy-6-methyl-2-pyrone into a 3-acetyltetramic acid.