261432

Methyl coumalate

98%

• Synonyme(s) : Methyl 2-oxo-2H-pyran-5-carboxylate, Methyl 2-pyrone-5-carboxylate
• Formule empirique (notation de Hill) : C₇H₆O₄
• CAS Number: 6018-41-3
• Poids moléculaire : 154.12
• Beilstein: 126301
• Numéro CE : 227-871-1
• Numéro MDL: MFCD00010120
• Code UNSPSC : 12352100
• ID de substance PubChem : 24855810
• Nomenclature NACRES : NA.22

Propriétés

• Essai: 98%
• Forme: solid
• pb: 178-180 °C/60 mmHg (lit.)
• Pf: 65-67 °C (lit.)
• Groupe fonctionnel: ester
• Chaîne SMILES: COC(=O)C1=COC(=O)C=C1
• InChI: 1S/C7H6O4/c1-10-7(9)5-2-3-6(8)11-4-5/h2-4H,1H3
• Clé InChI: HHWWWZQYHPFCBY-UHFFFAOYSA-N

Description

Description générale

Methyl coumalate is a 2-pyrone and acts as dienophile in Diels-Alder reaction. It reacts with 1,3-butadienes at 100°C to yield tetrahydrocoumarins and 4-methoxycarbonyltricyclo[3.2.1.0^2,7]octenes. It also reacts with cyclohexadiene to afford tetrahydronaphthalene-2-carboxylate. It undergoes Diels-Alder reaction with unactivated alkenes to afford para-substituted adducts.

Application

Methyl coumalate has been used as reagent in phosphine-catalyzed [4+3] annulation of modified allylic carbonates. It was also used in the preparation of 7-carboxyquinolizinium derivatives.

Informations sur la sécurité

• Code de la classe de stockage: 11 - Combustible Solids
• Classe de danger pour l'eau (WGK): WGK 3
• Point d'éclair (°F): Not applicable
• Point d'éclair (°C): Not applicable
• Équipement de protection individuelle: Eyeshields, Gloves, type N95 (US)