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226416

Sigma-Aldrich

α-Methylene-γ-butyrolactone

97%

Synonyme(s) :

alpha-Methylene-gamma-butyrolactone, 3-Methylenedihydro-2(3H)-furanone, Tulipane

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About This Item

Formule empirique (notation de Hill) :
C5H6O2
Numéro CAS:
Poids moléculaire :
98.10
Beilstein:
107939
Numéro MDL:
Code UNSPSC :
12352100
ID de substance PubChem :
Nomenclature NACRES :
NA.22

Essai

97%

Forme

liquid

Contient

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

Indice de réfraction

n20/D 1.472 (lit.)

pb

86-88 °C/12 mmHg (lit.)

Solubilité

water: soluble(lit.)

Densité

1.119 g/mL at 25 °C (lit.)

Groupe fonctionnel

ester

Température de stockage

2-8°C

Chaîne SMILES 

C=C1CCOC1=O

InChI

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

Clé InChI

GSLDEZOOOSBFGP-UHFFFAOYSA-N

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Application

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.

Pictogrammes

FlameExclamation mark

Mention d'avertissement

Warning

Mentions de danger

Classification des risques

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

Code de la classe de stockage

3 - Flammable liquids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

98.6 °F - closed cup

Point d'éclair (°C)

37 °C - closed cup

Équipement de protection individuelle

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


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Consulter la Bibliothèque de documents

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
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.
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

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