| Identification | Back Directory | [Name]
2,2,6,6-tetramethyl-2H-3,5,6-trihydropyran-4-one | [CAS]
1197-66-6 | [Synonyms]
2,2,6,6-tetramethyloxan-4-one
2,2,6,6-Tetramethyldihydropyran-4(3H)-one
tetrahydro-2,2,6,6-tetraMethylpyran-4-one
2,2,6,6-tetraMethyl-tetrahydropyran-4-one
2,2,6,6-Tetramethyltetrahydro-4H-pyran-4-one
Tetrahydro-2,2,6,6-tetraMethyl-4H-pyran-4-one
2,2,6,6-tetramethyldihydro-2H-pyran-4(3H)-one
4H-Pyran-4-one,tetrahydro-2,2,6,6-tetraMethyl-
2,2,6,6-tetramethyl-2H-3,5,6-trihydropyran-4-one | [Molecular Formula]
C9H16O2 | [MDL Number]
MFCD12828096 | [MOL File]
1197-66-6.mol | [Molecular Weight]
156.23 |
| Chemical Properties | Back Directory | [Melting point ]
12.8 °C | [Boiling point ]
73-75 °C(Press: 17 Torr) | [density ]
0.9485 g/cm3 | [storage temp. ]
Sealed in dry,Room Temperature | [Appearance]
Colorless to light yellow Liquid | [InChI]
InChI=1S/C9H16O2/c1-8(2)5-7(10)6-9(3,4)11-8/h5-6H2,1-4H3 | [InChIKey]
NOGFHTGYPKWWRX-UHFFFAOYSA-N | [SMILES]
C1(C)(C)OC(C)(C)CC(=O)C1 |
| Hazard Information | Back Directory | [Uses]
2,2,6,6-Tetramethyl-2h-3,5,6-trihydropyran-4-one is a chemical reagent used in the synthesis of Nodulisporic Acid, a potent and systemic insecticide. | [Synthesis]
General procedure for the synthesis of 2,2,6,6-tetramethyl-2H-3,5,6-trihydropyran-4-one using 2,6-dimethyl-2,5-heptadien-4-one as starting material: 5 g of 2,6-dimethyl-2,5-heptadien-4-one was dissolved in 36 mL of 1 M hydrochloric acid solution and the reaction was heated for 48 hours at 40 °C. Upon completion of the reaction, the reaction mixture was distilled (63-65 °C fraction was collected) to give 3.0 g of a light yellow oily product in 53% yield. The structure of the product was confirmed by 1H NMR (DMSO-d6, 400 MHz): δ 1.25 (m, 4H); 2.3 (m, 12H). | [References]
[1] Patent: WO2010/63773, 2010, A1. Location in patent: Page/Page column 23-24
[2] Journal of Medicinal Chemistry, 2018, vol. 61, # 4, p. 1425 - 1435
[3] Tetrahedron Letters, 1999, vol. 40, # 38, p. 6909 - 6912
[4] Patent: WO2015/23289, 2015, A1. Location in patent: Page/Page column 52
[5] Patent: US2015/51225, 2015, A1. Location in patent: Paragraph 0320; 0321 |
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