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Merck

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號碼:
分類程式碼代碼:
12352100
PubChem物質ID:
NACRES:
NA.22

化驗

97%

形狀

liquid

包含

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

折射率

n20/D 1.472 (lit.)

bp

86-88 °C/12 mmHg (lit.)

溶解度

water: soluble(lit.)

密度

1.119 g/mL at 25 °C (lit.)

儲存溫度

2-8°C

SMILES 字串

C=C1CCOC1=O

InChI

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

InChI 密鑰

GSLDEZOOOSBFGP-UHFFFAOYSA-N

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應用

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]

象形圖

FlameExclamation mark

訊號詞

Warning

危險聲明

危險分類

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

儲存類別代碼

3 - Flammable liquids

水污染物質分類(WGK)

WGK 3

閃點(°F)

98.6 °F - closed cup

閃點(°C)

37 °C - closed cup

個人防護裝備

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


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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.
Jean-Pierre Lepoittevin et al.
Chemical record (New York, N.Y.), 9(5), 258-270 (2009-11-26)
Natural products containing an alpha-methylene-gamma-butyrolactone moiety, mainly of the sesquiterpene type, are widely observed in plants, which upon coming into contact with skin, will induce major skin toxicological side effects or phytodermatitis. Indeed two main dermatological pathologies have been associated
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
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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