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Merck
CN

66735

α-亚甲基-γ-丁内酯

purum, ≥97.0% (GC)

别名:

2-甲烯基丁内酯, Tulipane

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经验公式(希尔记法):
C5H6O2
化学文摘社编号:
分子量:
98.10
PubChem Substance ID:
UNSPSC Code:
12352100
Beilstein/REAXYS Number:
107939
MDL number:
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SMILES string

C=C1CCOC1=O

InChI

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

InChI key

GSLDEZOOOSBFGP-UHFFFAOYSA-N

grade

purum

assay

≥97.0% (GC)

contains

~1% 2,6-di-tert-butyl-4-methylphenol as stabilizer

bp

86-88 °C/12 mmHg (lit.)

density

1.119 g/mL at 25 °C (lit.)

storage temp.

2-8°C

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Application

强反应性 Michael 受体;α-亚甲基-γ-丁内酯环系存在于许多具有生物学意义的天然产物中

pictograms

FlameExclamation mark

signalword

Warning

Hazard Classifications

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

存储类别

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

法规信息

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分析证书(COA)

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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
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
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
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
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

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