262102
5,6-Dihydro-2H-pyran-2-one
technical grade, 90%
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About This Item
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grade
technical grade
Assay
90%
form
liquid
refractive index
n20/D 1.483 (lit.)
bp
103 °C/10 mmHg (lit.)
density
1.139 g/mL at 25 °C (lit.)
functional group
ester
storage temp.
2-8°C
SMILES string
O=C1OCCC=C1
InChI
1S/C5H6O2/c6-5-3-1-2-4-7-5/h1,3H,2,4H2
InChI key
QBDAFARLDLCWAT-UHFFFAOYSA-N
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General description
Enantioselective conjugate addition of Grignard reagents to 5,6-dihydro-2H-pyran-2-one catalyzed by a chiral phosphine-copper iodide catalyst has been reported.
Application
5,6-Dihydro-2H-pyran-2-one has been used in the preparation of:
- (1aR,5aR,5bS,6S,7S)-6,7-di-tert-butoxy-5-oxo-pyrrolidino[1,2-b]isoxazolidino[4,5-c]tetrahydropyran
- 4-(phenyl)tetrahydro-2H-pyran-2-one
Signal Word
Warning
Hazard Statements
Hazard Classifications
Flam. Liq. 3
Storage Class Code
3 - Flammable liquids
WGK
WGK 3
Flash Point(F)
114.8 °F - closed cup
Flash Point(C)
46 °C - closed cup
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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(1aR,5aR,5bS,6S,7S)-6,7-Di-tert-butoxy-5-oxo-pyrrolidino[1,2-b]isoxazolidino[4,5-c]tetrahydropyran (8) prepared by (1,3)-dipolar cycloaddition of the cyclic nitrone 6 derived from tartaric acid to 5,6-dihydro-2H-pyran-2-one (7) was transformed into indolizidine 11 via a sequence of reactions involving methanolysis of the lactone ring, intramolecular alkylation of the nitrogen atom
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