384267
Methyl 3-butenoate
95%
Synonym(s):
Methyl vinylacetate
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About This Item
Linear Formula:
CH2=CHCH2COOCH3
CAS Number:
Molecular Weight:
100.12
Beilstein/REAXYS Number:
1741732
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
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assay
95%
form
liquid
refractive index
n20/D 1.409 (lit.)
bp
112 °C (lit.)
density
0.939 g/mL at 25 °C (lit.)
SMILES string
COC(=O)CC=C
InChI
1S/C5H8O2/c1-3-4-5(6)7-2/h3H,1,4H2,2H3
InChI key
GITITJADGZYSRL-UHFFFAOYSA-N
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General description
Methyl 3-butenoate is an olefin ester. It is reported to undergo Iron carbonyl-promoted isomerization to afford α, β-unsaturated esters. It is one of the reaction products formed during flash vacuum thermolysis of (−)-cocaine. The H2 and CH4 chemical ionization mass spectra of methyl 3-butenoate has been reported.
Application
Methyl 3-butenoate may be employed for the synthesis of dipeptide olefin isosteres using intermolecular olefin cross-metathesis.
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The flash vacuum thermolysis of (-)-cocaine.
Sisti NJ, et al.
Tetrahedron Letters, 30(44), 5977-5980 (1989)
Site of protonation in the chemical ionization mass spectra of olefinic methyl esters.
Harrison AX and Ichikawa H.
Org. Mass Spectrom., 15(5), 244-248 (1980)
Kuo-Chen Shih et al.
The Journal of organic chemistry, 61(22), 7784-7792 (1996-11-01)
Ultraviolet photolysis of stoichiometric amounts of methyl oleate and Fe(CO)(5) in hexanes solvent at 0 degrees C gives Fe(CO)(3)(eta(4)-alpha,beta-ester) in which the alpha,beta-unsaturated ester isomer of methyl oleate is stabilized by eta(4)-oxadiene pi coordination of the olefin and ester carbonyl
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The Journal of organic chemistry, 67(17), 6240-6242 (2002-08-17)
An approach to the synthesis of dipeptide olefin isosteres using intermolecular olefin cross-metathesis is presented. In particular, a synthesis of the Pro-Gly isostere (1) is reported. Conversion of N-BOC-proline into the corresponding vinyl-substituted carbamate provides the N-terminal cross-metathesis partner (2).
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