335274
2,2-Dimethyl-3(2H)-furanone
96%
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About This Item
Empirical Formula (Hill Notation):
C6H8O2
CAS Number:
Molecular Weight:
112.13
UNSPSC Code:
12352100
PubChem Substance ID:
MDL number:
Assay:
96%
Form:
liquid
InChI
1S/C6H8O2/c1-6(2)5(7)3-4-8-6/h3-4H,1-2H3
SMILES string
CC1(C)OC=CC1=O
InChI key
HVNICCSXGONRCB-UHFFFAOYSA-N
assay
96%
form
liquid
refractive index
n20/D 1.455 (lit.)
bp
46-47 °C/18 mmHg (lit.)
density
1.027 g/mL at 25 °C (lit.)
storage temp.
2-8°C
General description
2,2-Dimethyl-3(2H)-furanone is an β-oxo enol ether. Conjugate addition of 2,2-dimethyl-3(2H)-furanone to organocuprates has been reported. Photoannelation of alkenes to 2,2-dimethyl-3(2H)-furanone yields cyclohexenone.
Application
2,2-Dimethyl-3(2H)-furanone was used in the synthesis of epoxides via epoxidation. It was also used in the preparation of racemic methyl nonactate.
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Stereoselective synthesis of (.+-.) methyl nonactate.
Baldwin SW and McIver JM.
The Journal of Organic Chemistry, 52(2), 320-322 (1987)
Dimethyldioxirane epoxidation of ?-oxo enol ethers.
Adam W and Hadjiarapoglou L.
Chemische Berichte, 123(10), 2077-2079 (1990)
Cyclohexenones by the photoannelation of alkenes with 2, 2-dimethyl-3 (2H)-furanone.
Baldwin SW and Wilkinson JM.
Tetrahedron Letters, 20(29), 2657-2660 (1979)
Conjugated Addition to 2, 2-Dimethyl-3 (2h)-furanone: Support for the Baldwin Rules for Ring Closure.
Smith AB and Jerris PJ.
Synthetic Communications, 8(7), 421-426 (1978)
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