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Merck
CN

226416

Sigma-Aldrich

α-亚甲基-γ-丁内酯

97%

别名:

2-甲烯基丁内酯, Tulipane

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About This Item

经验公式(希尔记法):
C5H6O2
CAS号:
分子量:
98.10
Beilstein:
107939
MDL编号:
UNSPSC代码:
12352100
PubChem化学物质编号:
NACRES:
NA.22

质量水平

方案

97%

表单

liquid

包含

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

折射率

n20/D 1.472 (lit.)

沸点

86-88 °C/12 mmHg (lit.)

溶解性

water: soluble(lit.)

密度

1.119 g/mL at 25 °C (lit.)

官能团

ester

储存温度

2-8°C

SMILES字符串

C=C1CCOC1=O

InChI

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

InChI key

GSLDEZOOOSBFGP-UHFFFAOYSA-N

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应用

α-亚甲基-γ-丁内酯(Tulipane)可用于通过Cu(I)催化外消旋选择性1,3-偶极环加成偶氮甲碱叶立德,从而开发光学活性螺型-[丁内酯-吡咯烷]

象形图

FlameExclamation mark

警示用语:

Warning

危险声明

危险分类

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

储存分类代码

3 - Flammable liquids

WGK

WGK 3

闪点(°F)

98.6 °F - closed cup

闪点(°C)

37 °C - closed cup

个人防护装备

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

法规信息

危险化学品

历史批次信息供参考:

分析证书(COA)

Lot/Batch Number

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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.
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
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
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
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

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