261432

Methylcumalat

98%

• Synonym(e): 2-Oxo-2H-pyran-5-carbonsäure-methylester, 2-Pyron-5-carbonsäure-methylester
• Empirische Formel (Hill-System): C₇H₆O₄
• CAS-Nummer: 6018-41-3
• Molekulargewicht: 154.12
• Beilstein: 126301
• EG-Nummer: 227-871-1
• MDL-Nummer: MFCD00010120
• UNSPSC-Code: 12352100
• PubChem Substanz-ID: 24855810
• NACRES: NA.22

Eigenschaften

• Assay: 98%
• Form: solid
• bp: 178-180 °C/60 mmHg (lit.)
• mp (Schmelzpunkt): 65-67 °C (lit.)
• SMILES String: 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
• InChIKey: HHWWWZQYHPFCBY-UHFFFAOYSA-N

Beschreibung

Allgemeine Beschreibung

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.

Anwendung

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.

Sicherheitshinweise

• Lagerklassenschlüssel: 11 - Combustible Solids
• WGK: WGK 3
• Flammpunkt (°F): Not applicable
• Flammpunkt (°C): Not applicable
• Persönliche Schutzausrüstung: Eyeshields, Gloves, type N95 (US)