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
Quality Level
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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Conjugate addition of diethylzinc to a, ?-unsaturated lactones catalyzed by copper-phosphite complexes.
Chemical Communications (Cambridge, England), 2, 115-116 (2000)
Carbohydrate research, 336(4), 315-318 (2001-12-01)
(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
Rhodium-catalyzed asymmetric 1, 4-addition of arylboron reagents to α,β-unsaturated esters.
Tetrahedron Asymmetry, 10(20), 4047-4056 (1999)
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The inhibition of the zinc enzyme carbonic anhydrase (CA, EC 4.2.1.1) with (thio)coumarins has been recently reported (Maresca et al., J. Am. Chem. Soc. 2009, 131, 3057). Here we demonstrate that a series of γ- and δ-(thio)lactones also act as
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