261432

Methyl coumalate

98%

• Sinonimo/i: Methyl 2-oxo-2H-pyran-5-carboxylate, Methyl 2-pyrone-5-carboxylate
• Formula empirica (notazione di Hill): C₇H₆O₄
• Numero CAS: 6018-41-3
• Peso molecolare: 154.12
• Beilstein: 126301
• Numero CE: 227-871-1
• Numero MDL: MFCD00010120
• Codice UNSPSC: 12352100
• ID PubChem: 24855810
• NACRES: NA.22

Proprietà

• Saggio: 98%
• Forma fisica: solid
• P. eboll.: 178-180 °C/60 mmHg (lit.)
• Punto di fusione: 65-67 °C (lit.)
• Stringa SMILE: 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; HHWWWZQYHPFCBY-UHFFFAOYSA-N

Descrizione

Descrizione generale

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.

Applicazioni

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.

Informazioni sulla sicurezza

• Codice della classe di stoccaggio: 11 - Combustible Solids
• Classe di pericolosità dell'acqua (WGK): WGK 3
• Punto d’infiammabilità (°F): Not applicable
• Punto d’infiammabilità (°C): Not applicable
• Dispositivi di protezione individuale: Eyeshields, Gloves, type N95 (US)