226416
α-Methylene-γ-butyrolactone
97%
Synonym(s):
alpha-Methylene-gamma-butyrolactone, 3-Methylenedihydro-2(3H)-furanone, Tulipane
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About This Item
Empirical Formula (Hill Notation):
C5H6O2
CAS Number:
Molecular Weight:
98.10
NACRES:
NA.22
UNSPSC Code:
12352100
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
107939
Assay:
97%
Form:
liquid
Quality Level
assay
97%
form
liquid
contains
~2% 2,6-di-tert-butyl-p-cresol as stabilizer
refractive index
n20/D 1.472 (lit.)
bp
86-88 °C/12 mmHg (lit.)
solubility
water: soluble(lit.)
density
1.119 g/mL at 25 °C (lit.)
functional group
ester
storage temp.
2-8°C
SMILES string
C=C1CCOC1=O
InChI
1S/C5H6O2/c1-4-2-3-7-5(4)6/h1-3H2
InChI key
GSLDEZOOOSBFGP-UHFFFAOYSA-N
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.
signalword
Warning
hcodes
Hazard Classifications
Aquatic Chronic 3 - Flam. Liq. 3 - Skin Sens. 1
Storage Class
3 - Flammable liquids
flash_point_f
98.6 °F - closed cup
flash_point_c
37 °C - closed cup
ppe
Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
Regulatory Information
危险化学品
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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.
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
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
Global Trade Item Number
| SKU | GTIN |
|---|---|
| 226416-1G | 04061838780201 |
| 226416-5G | 04061838780218 |