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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

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.)

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

Analysenzertifikate (COA)

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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.
Joëlle Moïse et al.
Organic letters, 9(9), 1695-1698 (2007-04-05)
[reaction: see text] Olefin cross-metathesis between alpha-methylene-gamma-butyrolactone and terminal olefins is described. Moderate to excellent yields of alpha-alkylidene-gamma-butyrolactones were obtained with high E-stereoselectivity in the presence of low catalyst loading in refluxing CH2Cl2. In addition, the use of various additives
Taiji Nomura et al.
Plant physiology, 159(2), 565-578 (2012-04-05)
Tuliposides, the glucose esters of 4-hydroxy-2-methylenebutanoate and 3,4-dihydroxy-2-methylenebutanoate, are major secondary metabolites in tulip (Tulipa gesneriana). Their lactonized aglycons, tulipalins, function as defensive chemicals due to their biological activities. We recently found that tuliposide-converting enzyme (TCE) purified from tulip bulbs
Javier A Menendez et al.
Drug news & perspectives, 18(6), 375-385 (2005-10-26)
Fatty acid synthase (FAS)-catalyzed de novo fatty acid biosynthesis, an anabolic energy-storage pathway largely considered of minor importance in humans, actively contributes to the cancer phenotype by virtue of its ability to specifically regulate the expression and activity of Her-2/neu
Fernando Torres et al.
Cancer letters, 269(1), 139-147 (2008-06-03)
In this study, we investigated the effect of three synthetic alpha-methylene-gamma-butyrolactones (MBL) on viability of 10 human tumor cell lines and found that these lactones were highly cytotoxic against leukemia cells. Studies performed on HL-60 cells indicate that MBL induce
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