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]。
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
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
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
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
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