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226416

Sigma-Aldrich

α-Methylene-γ-butyrolactone

97%

Sinonimo/i:

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

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About This Item

Formula empirica (notazione di Hill):
C5H6O2
Numero CAS:
547-65-9
Peso molecolare:
98.10
Beilstein:
107939
Numero MDL:
MFCD00005407
Codice UNSPSC:
12352100
ID PubChem:
24853566
NACRES:
NA.22

Livello qualitativo

200

Saggio

97%

Forma fisica

liquid

contiene

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

Indice di rifrazione

n20/D 1.472 (lit.)

P. eboll.

86-88 °C/12 mmHg (lit.)

Solubilità

water: soluble(lit.)

Densità

1.119 g/mL at 25 °C (lit.)

Temperatura di conservazione

2-8°C

Stringa SMILE

C=C1CCOC1=O

InChI

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

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Categorie correlate

Applicazioni

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.

Pittogrammi

FlameExclamation mark
GHS02,GHS07

Avvertenze

Warning

Indicazioni di pericolo

H226 - H317 - H412

Classi di pericolo

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

Codice della classe di stoccaggio

3 - Flammable liquids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

98.6 °F - closed cup

Punto d’infiammabilità (°C)

37 °C - closed cup

Dispositivi di protezione individuale

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

Certificati d'analisi (COA)

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δ-Valerolactone technical grade

Sigma-Aldrich

389579

δ-Valerolactone

α-Hydroxy-γ-butyrolactone technical grade

Sigma-Aldrich

364037

α-Hydroxy-γ-butyrolactone

(S)-(−)-5-Hydroxymethyl-2(5H)-furanone 98%

Sigma-Aldrich

346861

(S)-(−)-5-Hydroxymethyl-2(5H)-furanone

(S)-β-Hydroxy-γ-butyrolactone 96%

Sigma-Aldrich

422797

(S)-β-Hydroxy-γ-butyrolactone

MB-3 ≥95% (HPLC)

Sigma-Aldrich

M2449

MB-3

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.
T Patrick Montgomery et al.
Journal of the American Chemical Society, 134(27), 11100-11103 (2012-06-28)
Upon exposure of acrylic ester 1 to alcohols 2a-i in the presence of a cyclometalated iridium catalyst modified by (-)-TMBTP, catalytic C-C coupling occurs, providing enantiomerically enriched 5-substituted α-exo-methylene γ-butyrolactones 3a-i. Bromination of the methylene butyrolactone products followed by zinc-mediated
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
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
David M Hodgson et al.
Organic letters, 13(10), 2594-2597 (2011-04-15)
Zinc or a chromium(II) source with 3-(bromomethyl)furan-2(5H)-one (3) and an aldehyde gives β-(hydroxymethylaryl/alkyl)-α-methylene-γ-butyrolactones 5 in good yields and high diastereoselectivities. The methodology is demonstrated in concise syntheses of (±)-hydroxymatairesinol (8) and (±)-methylenolactocin (10) by subsequent arylboronate conjugate addition and translactonization
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