| Identification | More | [Name]
Methyl coumalate | [CAS]
6018-41-3 | [Synonyms]
METHYL 2H-PYRAN-2-OXO-5-CARBOXYLATE
METHYL 2-OXO-2H-PYRAN-5-CARBOXYLATE
METHYL COUMALATE
METHYL PYR-2-ONE-5-CARBOXYLATE
TIMTEC-BB SBB000117
5-(Carbomethoxy)-2-pyrone
6-Oxo-6H-pyran-3-carboxylicacidmethylester
Coumalic acid methyl ester
Glutaconic acid, 4-(hydroxymethylene)-, delta-lactone, methyl ester
Methyl 2-pyrone-5-carboxylate
Methyl pyr-2-one-5-carboxylate,Methyl coumalate
Methyl 2-oxo-2H-pyran-5-carboxylate 97%
Methyl 2-oxo-2H-pyran-5-carboxylate, Methyl 2-pyrone-5-carboxylate
2-Oxo-2H-pyran-5-carboxylic acid methyl ester | [EINECS(EC#)]
227-871-1 | [Molecular Formula]
C7H6O4 | [MDL Number]
MFCD00010120 | [Molecular Weight]
154.12 | [MOL File]
6018-41-3.mol |
| Chemical Properties | Back Directory | [Melting point ]
65-67 °C (lit.) | [Boiling point ]
178-180 °C/60 mmHg (lit.) | [density ]
1.1993 (rough estimate) | [refractive index ]
1.4300 (estimate) | [Fp ]
178-180°C/60mm | [storage temp. ]
Inert atmosphere,Room Temperature | [solubility ]
Freely soluble in dichloromethane. | [form ]
powder to crystal | [color ]
White to Orange to Green | [Merck ]
14,2557 | [BRN ]
126301 | [InChI]
InChI=1S/C7H6O4/c1-10-7(9)5-2-3-6(8)11-4-5/h2-4H,1H3 | [InChIKey]
HHWWWZQYHPFCBY-UHFFFAOYSA-N | [SMILES]
C1(=O)OC=C(C(OC)=O)C=C1 | [LogP]
-0.660 (est) | [CAS DataBase Reference]
6018-41-3(CAS DataBase Reference) | [NIST Chemistry Reference]
2H-Pyran-5-carboxylic acid, 2-oxo-, methyl ester(6018-41-3) |
| Hazard Information | Back Directory | [Uses]
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. | [Uses]
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[3.2.1.02,7]octenes. It also reacts with cyclohexadiene to afford tetrahydronaphthalene-2-carboxylate. It undergoes Diels-Alder reaction with unactivated alkenes to afford para-substituted adducts. It 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. | [Uses]
α, β-Unsaturated ketone Methyl Coumalate showed cytotoxicity against human normal gingival fibroblast cells and oral squamous cell carcinoma cell line-2. | [General Description]
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[3.2.1.02,7]octenes. It also reacts with cyclohexadiene to afford tetrahydronaphthalene-2-carboxylate. It undergoes Diels-Alder reaction with unactivated alkenes to afford para-substituted adducts. | [Synthesis]
General procedure for the synthesis of methyl coumalate from coumaric acid: diisopropylethylamine was added to a suspension of coumaric acid (115.5 g) in N-methylpyrrolidone (600 mL) at 25 °C. Subsequently, dimethyl sulfate (100.9 g) was slowly added over a period of 1 hour and the reaction mixture was stirred continuously for 2 hours at 25°C. After completion of the reaction, the reaction mixture was diluted with toluene and extracted sequentially with water, sodium bicarbonate solution and water. Afterwards, toluene was removed under vacuum. The crude product, methyl coumalate, was purified by short distillation or crystallization combined with grinding. Finally, after removal of residual solvent by vacuum evaporation, methyl coumalate (78.8 g, 99% purity, 64% yield) was obtained. | [References]
[1] Patent: WO2004/792, 2003, A1. Location in patent: Page 15
[2] Tetrahedron Letters, 1983, vol. 24, # 17, p. 1771 - 1774
[3] Liebigs Annalen der Chemie, 1990, p. 233 - 238 |
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