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| | 4-Hydroxy-6-methyl-2-pyrone Basic information |
| | 4-Hydroxy-6-methyl-2-pyrone Chemical Properties |
| Melting point | 188-190 °C (dec.) (lit.) | | Boiling point | 174.21°C (rough estimate) | | density | 1.2048 (rough estimate) | | refractive index | 1.4189 (estimate) | | storage temp. | Keep in dark place,Sealed in dry,Room Temperature | | solubility | 8.6g/l | | pka | 5.14±0.30(Predicted) | | form | Powder | | color | Off-white to brown | | Water Solubility | 8.60 g/L (20 ºC) | | BRN | 113815 | | InChI | InChI=1S/C6H6O3/c1-4-2-5(7)3-6(8)9-4/h2-3,7H,1H3 | | InChIKey | NSYSSMYQPLSPOD-UHFFFAOYSA-N | | SMILES | C1(=O)OC(C)=CC(O)=C1 | | CAS DataBase Reference | 675-10-5(CAS DataBase Reference) | | EPA Substance Registry System | 2H-Pyran-2-one, 4-hydroxy-6-methyl- (675-10-5) |
| Hazard Codes | Xi | | Risk Statements | 36/37/38 | | Safety Statements | 26-36-37/39 | | WGK Germany | 3 | | RTECS | UQ1000000 | | Hazard Note | Irritant | | TSCA | TSCA listed | | HS Code | 29322980 | | Storage Class | 11 - Combustible Solids | | Hazard Classifications | Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| | 4-Hydroxy-6-methyl-2-pyrone Usage And Synthesis |
| Chemical Properties | white to light yellow crystal powder | | Uses | 4-Hydroxy-6-methylpyran-2-one was used in the synthesis of pyrano[3,2-c]pyridones with antiproliferative and apoptosis inducing activities. It was also used in the design of benzisothiazolone human leukocyte elastase inhibitors. | | Definition | ChEBI: Triacetate lactone is a member of 2-pyranones. It is a conjugate acid of a triacetate lactone oxoanion. | | Synthesis Reference(s) | Synthetic Communications, 20, p. 1931, 1990 DOI: 10.1080/00397919008053123 | | Synthesis | 14.4g (0.1mol) isopropylidene malonate, 35ml dichloromethane and 15ml chlorobenzene were placed in the reaction flask, cooled to <5C under stirring, 10.1g (0.1mol) triethylamine and 10.1g (0.12mol) bis(vinylidene) ketone were added dropwise. After addition, slowly warmed to room temperature, continue to stir for 2 hours. The reaction was washed with cooled dilute hydrochloric acid, dried, filtered and most of the dichloromethane was removed in a rotary evaporator. The residual reactant was heated and refluxed for 2 hours, and yellow crystals were precipitated. The crystals were cooled, filtered and washed with a small amount of ether. After drying, 4-hydroxy-6-methyl-2-pyranone was obtained 10.1g, yield 82%, m.p. 186-189 (literature value 188-189 ). |
| | 4-Hydroxy-6-methyl-2-pyrone Preparation Products And Raw materials |
| Raw materials | 6-Acetonyl-4-hydroxy-2-pyrone-->1,3-Dioxane-4,6-dione, 5-(1-hydroxy-3-oxobutylidene)-2,2-dimethyl--->5-18-08-00154 (Beilstein Handbook Reference)-->2,2-dimethyl-6-(2-oxopropyl)-1,3-dioxin-4-one-->4-Hydroxy-5,6-dimethylpyran-2-one-->4-Acetyl-3-oxobutanoic Acid-->S-(hydrogen malonyl)coenzyme A-->1-PHENYL-1-TRIMETHYLSILOXYETHYLENE-->DEHYDROACETIC ACID-->ACETYL COENZYME A TRILITHIUM SALT TRIHYDRATE-->Dehydroacetic acid-->Malonyl chloride | | Preparation Products | 4,6-Dimethyl-2-pyrone-->2,4-DICHLORO-6-METHYL-3-NITROPYRIDINE-->3-Nitro-4-hydroxy-6-methyl-2H-pyran-2-one-->(5AS,7S)-7-ISOPROPENYL-3-METHYL-6,7,8,9-TETRAHYDRO-5AH-PYRANO[4,3-B]CHROMEN-1-ONE-->2-amino-4-(3-methoxyphenyl)-7-methyl-5-oxo-4H,5H-pyrano[3,2-c]pyran-3-carbonitrile |
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