α-亚甲基-γ-丁内酯

≥95%
contains~2% 2,6-di-tert-butyl-p-cresol as stabilizer

CAS编号: 547-65-9
分子式: C₅H₆O₂
分子量: 98.1
Beilstein号: 107939
MDL号: MFCD00005407
PubChem编号: 68352

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货号 (SKU)	包装规格	是否现货
M108009-200mg	200mg	期货
M108009-1g	1g	现货
M108009-5g	5g	现货
M108009-25g	25g	现货
M108009-100g	100g	现货

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Drug Metabolite (242) Metabolic Enzyme/Protease (4886) 丙烯酸单体 (125) 羰基化合物 (2340)

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基本描述

别名	2-甲烯基丁内酯 \| 二氢-3-亚甲基-2(3H)-呋喃酮
英文别名	a-methylene-y-butyrolactone \| .ALPHA.-METHYLENE BUTYROLACTONE [MI] \| Tulipane \| 2(3H)-Furanone, dihydro-3-methylene- \| 3-methylenedihydrofuran-2(3H)-one \| LMSV-6 \| .alpha.-Methylene-.gamma.-butyrolactone \| alpha-methylidene-gamma-butyrolactone \| 3-Methyle
规格或纯度	≥95%, contains~2% 2,6-di-tert-butyl-p-cresol as stabilizer
英文名称	α-Methylene-γ-butyrolactone
应用	α-Methylene-γ-butyrolactone (Tulipane) was used to develop optically active spiro-[butyrolactone-pyrrolidine] via Cu(I)-catalyzed exo-selective 1,3-dipolar cycloaddition of azomethine ylides.
储存温度	2-8°C储存,避光,充氩
运输条件	冰袋运输
产品介绍	α-Methylene-γ-butyrolactone (Tulipane) was used to develop optically active spiro-[butyrolactone-pyrrolidine] via Cu(I)-catalyzed exo-selective 1,3-dipolar cycloaddition of azomethine ylides. α-Methylene-γ-butyrolactone (Tulipane) was used to develop optically active spiro-[butyrolactone-pyrrolidine] via Cu(I)-catalyzed exo-selective 1,3-dipolar cycloaddition of azomethine ylides.

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关联靶点（人）

CAKI-1 (44928 活性数据)

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HL-60 (67320 活性数据)

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KB (17409 活性数据)

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关联靶点（其它种属）

Pseudomonas aeruginosa (123386 活性数据)

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Escherichia coli (133304 活性数据)

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Bacillus subtilis (32866 活性数据)

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Cavia porcellus (23802 活性数据)

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Rattus norvegicus (775804 活性数据)

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P388 (20296 活性数据)

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Plutella xylostella (1838 活性数据)

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Nilaparvata lugens (786 活性数据)

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Spodoptera litura (1708 活性数据)

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Trichophyton mentagrophytes (4846 活性数据)

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Frankliniella occidentalis (90 活性数据)

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Frankliniella intonsa (12 活性数据)

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Thrips palmi (12 活性数据)

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作用机制

作用机制	Action Type	target ID	Target Name	Target Type	Target Organism	Binding Site Name	参考文献

名称和识别符

分子类型	小分子
IUPAC Name	3-methylideneoxolan-2-one
INCHI	InChI=1S/C5H6O2/c1-4-2-3-7-5(4)6/h1-3H2
InChi Key	GSLDEZOOOSBFGP-UHFFFAOYSA-N
Canonical SMILES	C=C1CCOC1=O
Isomeric SMILES	C=C1CCOC1=O
WGK Germany	3
RTECS	LU3580400
UN Number	1993
分子量	98.1
Beilstein号	107939
Reaxy-Rn	107939

化学和物理性质

溶解性	可溶于水
密度	1.119
敏感性	对湿度&空气&光线&热敏感
折光率	1.472
闪点(℉)	98.6 °F
闪点(℃)	90 °C
沸点	86-88 °C
分子量	98.100 g/mol
XLogP3	0.800
氢键供体数Hydrogen Bond Donor Count	0
氢键受体数Hydrogen Bond Acceptor Count	2
可旋转键计数Rotatable Bond Count	0
精确质量Exact Mass	98.0368 Da
单同位素质量Monoisotopic Mass	98.0368 Da
拓扑极表面积Topological Polar Surface Area	26.300 Å²
重原子数Heavy Atom Count	7
形式电荷Formal Charge	0
复杂度Complexity	115.000
同位素原子数Isotope Atom Count	0
定义的原子立体中心计数Defined Atom Stereocenter Count	0
未定义的原子立体中心计数Undefined Atom Stereocenter Count	0
定义的键立体中心计数Defined Bond Stereocenter Count	0
未定义的键立体中心计数Undefined Bond Stereocenter Count	0
所有立体化学键的总数The total count of all stereochemical bonds	0
共价键合单元计数Covalently-Bonded Unit Count	1

安全和危险性（GHS）

象形图	GHS07, GHS02
信号词	Warning
危险声明	H317: 可能引起皮肤过敏反应 H226: 易燃液体和蒸气
预防措施声明	P261: 避免吸入灰尘/烟雾/气体/雾/蒸汽/喷雾 P280: 戴防护手套/穿防护服/戴防护眼罩/戴防护面具。 P370+P378: 火灾时：使用干砂、干粉或抗醇泡沫灭火。 P210: 远离热源，热表面，火花，明火和其他点火源。 - 禁止抽烟。 P302+P352: 如皮肤沾染：用水充分清洗。 P321: 特殊处理（请参阅此标签上的...）。 P501: 将内容物/容器处理到。。。 P233: 保持容器密闭。 P240: 地面/粘结容器和接收设备 P403+P235: 存放在通风良好的地方。保持低温。 P303+P361+P353: 如皮肤（或头发）沾染：立即脱掉所有沾染的衣服。用水清洗皮肤/淋浴。 P241: 使用防爆的[电气/通风/照明/.../]设备。 P272: 被污染的工作服不允许离开工作场所 P333+P313: 如发生皮肤刺激或皮疹：求医/就诊。 P362+P364: 脱掉沾污的衣服，清洗后方可重新使用。 P242: 仅使用无火花的工具。 P243: 采取防静电措施
WGK Germany	3
RTECS	LU3580400
Reaxy-Rn	107939
Merck Index	6062
个人防护装备	Eyeshields,Faceshields,full-face respirator (US),Gloves,multi-purpose combination respirator cartridge (US),type ABEK (EN14387) respirator filter

技术规格说明书

Purity(GC)	95-100（%）
Refractive index n20/D	1.471-1.475
Density (20°C)	1.119-1.126
Appearance（M108009)	Colorless to light yellow liquid
Infrared spectrum	Conforms to Structure
Proton NMR spectrum	Conforms to Structure
Stabilizer（~2% 2,6-Di-tert-butyl-p-cresol）	Conforms

技术规格说明书 SDS英文版

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找到10个结果

批号(Lot Number)	证书类型	日期	货号
D2508067	分析证书	25-04-09	M108009
L2426403	分析证书	24-04-10	M108009
E2204110	分析证书	24-02-22	M108009
E2204132	分析证书	24-02-22	M108009
E2204140	分析证书	24-02-22	M108009
E2204147	分析证书	24-02-22	M108009
G1714059	分析证书	23-12-06	M108009
H1531046	分析证书	23-06-06	M108009
H1809040	分析证书	22-06-15	M108009
H1809041	分析证书	22-06-15	M108009

参考文献

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3. Raffaele Ieva,Cristina Alaimo,Isabel Delany,Gunther Spohn,Rino Rappuoli,Vincenzo Scarlato. (2005-05-04) CrgA is an inducible LysR-type regulator of Neisseria meningitidis, acting both as a repressor and as an activator of gene transcription.. Journal of bacteriology, 187 ((10)): (3421-3430). [PMID:15866928]
4. Mickaël Jean,Myriam Le Roch,Jacques Renault,Philippe Uriac. (2005-06-17) Synthesis of a laterally branched polyamine from alpha-methylene-gamma-butyrolactone.. Organic letters, 7 ((13)): (2663-2665). [PMID:15957916]
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6. Joëlle Moïse,Stellios Arseniyadis,Janine Cossy. (2007-04-05) Cross-metathesis between alpha-methylene-gamma-butyrolactone and olefins: a dramatic additive effect.. Organic letters, 9 ((9)): (1695-1698). [PMID:17407299]
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9. Russell R A Kitson,Alessia Millemaggi,Richard J K Taylor. (2009-11-26) The renaissance of alpha-methylene-gamma-butyrolactones: new synthetic approaches.. Angewandte Chemie (International ed. in English), 48 ((50)): (9426-9451). [PMID:19938025]
10. Z K Binienda,I A Ross,B Gough,T Riccio,C S Kim,S F Ali. (2009-12-23) Striatal dopamine in the response of brain and liver unsaturated and saturated free fatty acids following administration of C75 in CD-1 mice.. Neuroscience letters, 469 ((3)): (324-327). [PMID:20026180]
11. Thomas Mendgen,Therese Scholz,Christian D Klein. (2010-08-24) Structure-activity relationships of tulipalines, tuliposides, and related compounds as inhibitors of MurA.. Bioorganic & medicinal chemistry letters, 20 ((19)): (5757-5762). [PMID:20729083]
12. David M Hodgson,Eric P A Talbot,Barry P Clark. (2011-04-15) Stereoselective synthesis of β-(hydroxymethylaryl/alkyl)-α-methylene-γ-butyrolactones.. Organic letters, 13 ((10)): (2594-2597). [PMID:21488628]
13. Taiji Nomura,Shinjiro Ogita,Yasuo Kato. (2012-04-05) A novel lactone-forming carboxylesterase: molecular identification of a tuliposide A-converting enzyme in tulip.. Plant physiology, 159 ((2)): (565-578). [PMID:22474185]
14. T Patrick Montgomery,Abbas Hassan,Boyoung Y Park,Michael J Krische. (2012-06-28) Enantioselective conversion of primary alcohols to α-exo-methylene γ-butyrolactones via iridium-catalyzed C-C bond-forming transfer hydrogenation: 2-(alkoxycarbonyl)allylation.. Journal of the American Chemical Society, 134 ((27)): (11100-11103). [PMID:22734694]
15. Jihoon Shin,Youngmin Lee,William B Tolman,Marc A Hillmyer. (2012-10-16) Thermoplastic elastomers derived from menthide and tulipalin A.. Biomacromolecules, 13 ((11)): (3833-3840). [PMID:23062206]
16. Yi Dong,Xiaoyong Guo,Yuanyuan Yu,Gang Liu. (2013-01-12) Highly stereoselective synthesis of (Z)- and (E)-chloro-substituted-α-methylene-γ-butyrolactone by possibly controlling cis- and trans-chloropalladation.. Molecular diversity, 17 ((1)): (1-7). [PMID:23307270]
17. Yusuke Murata,Masaki Takahashi,Fumitoshi Yagishita,Masami Sakamoto,Tetsuya Sengoku,Hidemi Yoda. (2013-11-15) Construction of spiro-fused 2-oxindole/α-methylene- γ-butyrolactone systems with extremely high enantioselectivity via indium-catalyzed amide allylation of N-methyl isatin.. Organic letters, 15 ((24)): (6182-6185). [PMID:24224753]
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20. Javier A Menendez,Ruth Lupu,Ramon Colomer. (2005-10-26) Targeting fatty acid synthase: potential for therapeutic intervention in her-2/neu-overexpressing breast cancer.. Drug news & perspectives, 18 ((6)): (375-385). [PMID:16247515]
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28. Qing-Hua Li,Tang-Lin Liu,Liang Wei,Xiang Zhou,Hai-Yan Tao,Chun-Jiang Wang. (2013-09-12) exo-Selective construction of spiro-[butyrolactone-pyrrolidine] via 1,3-dipolar cycloaddition of azomethine ylides with α-methylene-γ-butyrolactone catalyzed by Cu(I)/DTBM-BIPHEP.. Chemical communications (Cambridge, England), 49 ((83)): (9642-9644). [PMID:24022250]

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