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226416

Sigma-Aldrich

α-Methylen-γ-butyrolacton

97%

Synonym(e):

3-Methylendihydro-2(3H)-furanon, Tulipan

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About This Item

Empirische Formel (Hill-System):
C5H6O2
CAS-Nummer:
547-65-9
Molekulargewicht:
98.10
Beilstein:
107939
MDL-Nummer:
MFCD00005407
UNSPSC-Code:
12352100
PubChem Substanz-ID:
24853566
NACRES:
NA.22

Qualitätsniveau

200

Assay

97%

Form

liquid

Enthält

~2% 2,6-di-tert-butyl-p-cresol as stabilizer

Brechungsindex

n20/D 1.472 (lit.)

bp

86-88 °C/12 mmHg (lit.)

Löslichkeit

water: soluble(lit.)

Dichte

1.119 g/mL at 25 °C (lit.)

Funktionelle Gruppe

ester

Lagertemp.

2-8°C

SMILES String

C=C1CCOC1=O

InChI

1S/C5H6O2/c1-4-2-3-7-5(4)6/h1-3H2

InChIKey

GSLDEZOOOSBFGP-UHFFFAOYSA-N

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Anwendung

α-Methylene-γ-butyrolactone (Tulipane) was used to develop optically active spiro-[butyrolactone-pyrrolidine] via Cu(I)-catalyzed exo-selective 1,3-dipolar cycloaddition of azomethine ylides.

Piktogramme

FlameExclamation mark
GHS02,GHS07

Signalwort

Warning

Gefahreneinstufungen

Aquatic Chronic 3 - Flam. Liq. 3 - Skin Sens. 1

Lagerklassenschlüssel

3 - Flammable liquids

WGK

WGK 3

Flammpunkt (°F)

98.6 °F - closed cup

Flammpunkt (°C)

37 °C - closed cup

Persönliche Schutzausrüstung

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

Hier finden Sie alle aktuellen Versionen:

Analysenzertifikate (COA)

Lot/Batch Number
BCCK6710
BCCH7873
BCCG7008
BCCC9019
BCBZ5322

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Qing-Hua Li et al.
Chemical communications (Cambridge, England), 49(83), 9642-9644 (2013-09-12)
An expedient access to optically active spiro-[butyrolactone-pyrrolidine] was successfully developed via an unprecedented Cu(I)-catalyzed exo-selective 1,3-DC of azomethine ylides with α-methylene-γ-butyrolactone, which exhibited high diastereoselectivity (>98 : 2), excellent enantioselectivity (96->99% ee) and a broad substrate scope under mild conditions.
Sébastien Fuchs et al.
Photochemistry and photobiology, 86(3), 545-552 (2010-02-02)
(+) and (-) alpha-methylene-hexahydrobenzofuranone derivatives with a stereochemically pure cis ring junction were used as models of sesquiterpene lactones to study their photoreactivity toward thymidine. After 313 nm irradiation of a deoxygenated acetone solution of lactone models and thymidine, six
Francesca Cateni et al.
European journal of medicinal chemistry, 41(2), 192-200 (2005-12-22)
The synthesis of a series of alpha-methylene-gamma-butyrolactones (compounds 4a, 4b, 6-12, 16, 17) and alpha,beta-unsaturated-delta-lactones (compounds 19-23, 25, 26) starting from 4,4-dimethyldihydrofuran-2,3-dione (1) has been described. Their chemical structures were assigned by spectroscopic evidence. These new compounds exhibited significantly different
E Rozas-Muñoz et al.
Actas dermo-sifiliograficas, 103(6), 456-477 (2012-01-06)
Allergic contact dermatitis due to plants is common. Potentially allergenic plants and plant products are found in many everyday environments, such as the home, the garden, the workplace, and recreational settings. By improving our knowledge of allergenic plant-derived chemical compounds
YuZhe Gao et al.
Organic & biomolecular chemistry, 10(20), 3991-3998 (2012-04-25)
A zinc or indium-mediated Barbier-type allylation of aldehydes with 3-bromomethyl-5H-furan-2-one in aqueous solvents was developed to provide an efficient route to α-methylene-γ-butyrolactone, which is synthetically very useful. The desired products were obtained in moderate to high yields in aqueous solvents.
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