226416
α-亚甲基-γ-丁内酯
97%
别名:
2-甲烯基丁内酯, Tulipane
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关于此项目
经验公式（希尔记法）:
C5H6O2
化学文摘社编号:
分子量:
98.10
NACRES:
NA.22
UNSPSC Code:
12352100
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
107939
Assay:
97%
Form:
liquid
InChI
1S/C5H6O2/c1-4-2-3-7-5(4)6/h1-3H2
SMILES string
C=C1CCOC1=O
InChI key
GSLDEZOOOSBFGP-UHFFFAOYSA-N
assay
97%
form
liquid
contains
~2% 2,6-di-tert-butyl-p-cresol as stabilizer
refractive index
n20/D 1.472 (lit.)
bp
86-88 °C/12 mmHg (lit.)
solubility
water: soluble(lit.)
density
1.119 g/mL at 25 °C (lit.)
functional group
ester
storage temp.
2-8°C
Quality Level
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Application
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]。
signalword
Warning
hcodes
Hazard Classifications
Aquatic Chronic 3 - Flam. Liq. 3 - Skin Sens. 1
存储类别
3 - Flammable liquids
wgk
WGK 3
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
危险化学品
此项目有
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.
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
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
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
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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