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262102

Sigma-Aldrich

5,6-Dihydro-2H-pyran-2-one

technical grade, 90%

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About This Item

Empirical Formula (Hill Notation):
C5H6O2
CAS Number:
3393-45-1
Molecular Weight:
98.10
Beilstein:
1610
MDL number:
MFCD00010439
UNSPSC Code:
12352100
PubChem Substance ID:
24855858
NACRES:
NA.22

grade

technical grade

Quality Level

100

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.)

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

Pictograms

Flame
GHS02

Signal Word

Warning

Hazard Statements

H226

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Rhodium-catalyzed asymmetric 1, 4-addition of arylboron reagents to α,β-unsaturated esters.
Takaya Y, et al.
Tetrahedron Asymmetry, 10(20), 4047-4056 (1999)
Conjugate addition of diethylzinc to a, ?-unsaturated lactones catalyzed by copper-phosphite complexes.
Yan M, et al.
Chemical Communications (Cambridge, England), 2, 115-116 (2000)
D Socha et al.
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
Fabrizio Carta et al.
Bioorganic & medicinal chemistry letters, 22(1), 267-270 (2011-12-06)
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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