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安全信息

220868

Sigma-Aldrich

1-乙酰氧基-1,3-丁二烯（顺反异构体混合物）

mixture of cis and trans

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别名:
1-乙酰氧基-1,3-丁二烯
线性分子式:
CH2=CHCH=CHOCOCH3
CAS号:
1515-76-0
分子量:
112.13
Beilstein:
1743394
MDL编号:
MFCD00008714
PubChem化学物质编号:
24853196
NACRES:
NA.22

蒸汽压

40 mmHg ( 60 °C)

质量水平

100

形式

liquid

包含

0.1% p-tert-butylcatechol as stabilizer

折射率

n20/D 1.469 (lit.)

bp

60-61 °C/40 mmHg (lit.)

密度

0.945 g/mL at 25 °C (lit.)

储存温度

2-8°C

SMILES string

CC(=O)O\C=C\C=C

InChI

1S/C6H8O2/c1-3-4-5-8-6(2)7/h3-5H,1H2,2H3/b5-4+

InChI key

NMQQBXHZBNUXGJ-SNAWJCMRSA-N

一般描述

1-Acetoxy-1,3-butadiene (1-ABD) can be generated by potassium or sodium acetate catalyzed reaction between crotonaldehyde and acetic anhydride. The product is a mixture of cis and trans forms, that has been confirmed by its physical properties and IR spectra. It is reported to be formed as a major product during the acetoxylation of 1,3-butadiene (BD) in gas-phase in the presence of Pd-KOAc (palladium-potassium acetate) catalyst. 1-ABD participates as 2Π or 4Π diene in cycloaddition reactions. Enantioselective Diels Alder reaction of 2-methoxy-5-methyl-1,4-benzoquinone with 1-ABD in the presence of molecular sieves (mesh size:4Å) has been reported.

应用

1-Acetoxy-1,3-butadiene was used as diene in the following reactions:
  • Diels-Alder reaction with ortho-carbazolequinones to yield benzocarbazolequinone.
  • Diels-Alder reaction with diethyl ketovinylphosphonate, with and without Lewis acid assistance.
  • Diels-Alder reaction with methyl acrylate to yield racemic forms of 2-hydroxy-3-cyclohexenecarboxylic acid.

It was used for the reaction with dienophiles such as maleimides, a juglone, a butyne-1,4-dione and methyl 2-(4-methylphenyl)-2H-azirine-3-carboxylate and during visible light photocatalysis. It was also used as reactant during intermolecular oxa-Pictet-Spengler cyclization.

象形图

FlameSkull and crossbones
GHS02,GHS06

警示用语：

Danger

危险分类

Acute Tox. 3 Dermal - Acute Tox. 4 Oral - Eye Irrit. 2 - Flam. Liq. 3 - Skin Irrit. 2 - STOT SE 3

靶器官

Respiratory system

储存分类代码

3 - Flammable liquids

WGK

WGK 3

闪点(°F)

91.4 °F - closed cup

闪点(°C)

33 °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

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Cis and trans 1-acetoxy-1, 3-butadiene: physical and chemical properties, infrared and ultraviolet spectra.
Georgieff KK and Dupre A.
Canadian Journal of Chemistry, 38(7), 1070-1075 (1960)
Preparation of functionalized juglone acetates and juglones via 1, 4-dimethoxynaphthalene derivatives: synthesis of anthraquinones related to rhein and aloe-emodin.
Bloomer JL, et al.
The Journal of Organic Chemistry, 58(27), 7906-7906 (1993)
The Journal of Organic Chemistry, 58, 7146-7146 (1993)
Shishi Lin et al.
Journal of the American Chemical Society, 133(48), 19350-19353 (2011-10-29)
Ruthenium(II) polypyridyl complexes promote the efficient radical cation Diels-Alder cycloaddition of electron-rich dienophiles upon irradiation with visible light. These reactions enable facile [4 + 2] cycloadditions that would be electronically mismatched under thermal conditions. Key to the success of this
Journal of the Chemical Society. Perkin Transactions 1, 1925-1925 (1993)
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Diels–Alder Reaction

The Diels–Alder reaction is the reaction between a conjugated diene and an alkene (dienophile) to form unsaturated six-membered rings. It is also referred to as a cycloaddition.

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