220868
1-乙酰氧基-1,3-丁二烯（顺反异构体混合物）
mixture of cis and trans
别名:
1-乙酰氧基-1,3-丁二烯
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关于此项目
线性分子式:
CH2=CHCH=CHOCOCH3
化学文摘社编号:
分子量:
112.13
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
1743394
Form:
liquid
InChI
1S/C6H8O2/c1-3-4-5-8-6(2)7/h3-5H,1H2,2H3/b5-4+
SMILES string
CC(=O)O\C=C\C=C
InChI key
NMQQBXHZBNUXGJ-SNAWJCMRSA-N
vapor pressure
40 mmHg ( 60 °C)
form
liquid
contains
0.1% p-tert-butylcatechol as stabilizer
refractive index
n20/D 1.469 (lit.)
bp
60-61 °C/40 mmHg (lit.)
density
0.945 g/mL at 25 °C (lit.)
functional group
ester
storage temp.
2-8°C
Quality Level
General description
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.
Application
1-Acetoxy-1,3-butadiene was used as diene in the following reactions:
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.
- 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.
signalword
Danger
Hazard Classifications
Acute Tox. 3 Dermal - Acute Tox. 4 Oral - Eye Irrit. 2 - Flam. Liq. 3 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
存储类别
3 - Flammable liquids
wgk
WGK 3
flash_point_f
91.4 °F - closed cup
flash_point_c
33 °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
Methyl 2-(4-methylphenyl)-2H-azirine-3-carboxylate as dienophile in hetero-Diels-Alder cycloaddition: a DFT approach
P. Sharma, et al.
Letters in Organic Chemistry, 8, 132-137 (2011)
Muriel Compain-Batissou et al.
Chemical & pharmaceutical bulletin, 52(9), 1114-1116 (2004-09-02)
Oxidation of 2- and 3-hydroxycarbazoles with Frémy's salt gave the corresponding ortho-carbazolequinones. These molecules react as carbodienophiles in Diels-Alder reaction with 1-acetoxy-1,3-butadiene and 1,3-cyclopentadiene to provide the novel benzocarbazolequinone structures 15, 16, 18 and 19.
Enantio-face control by molecular sieves in the asymmetric Diels-Alder reaction
Moharram SM, et al.
Tetrahedron Letters, 41(34), 6669-6673 (2000)
Journal of the Chemical Society. Perkin Transactions 1, 1925-1925 (1993)
Synthesis and absolute configuration of the isomers of homoisocitric acid (1-hydroxy-1,2,4-butanetricarboxylic acid) and the stereochemistry of lysine biosynthesis.
K Chilina et al.
Biochemistry, 8(7), 2846-2855 (1969-07-01)
商品
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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