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CAS No.: | 5411-63-2 |
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Name: | 2-ButenaMide, N,N-diethyl-3-Methyl- |
Article Data: | 10 |
Molecular Structure: | |
Formula: | C9H17NO |
Molecular Weight: | 155.24 |
Synonyms: | N,N-Diaethyl-3-methyl-crotonamid;N,N-diethyl-3-methyl-but-2-enamide;N,N-dimethylamino-3,3-diethylacrylamide;N,N-Diethyl-3-methyl-2-butenamide;N,N-diethyl seneciamide;3-methyl-crotonic acid diethylamide;N,N-diethylsenecioamide;N,N-diethyl-3,3-dimethylacrylic amide; |
Density: | 0.887g/cm3 |
Boiling Point: | 259.3°Cat760mmHg |
Flash Point: | 109°C |
PSA: | 20.31000 |
LogP: | 1.82100 |
3,3-Dimethylacryloyl chloride
diethylamine
N,N-dimethylamino-3,3-diethylacrylamide
Conditions | Yield |
---|---|
90% | |
With diethyl ether |
n-butyllithium
N,N-diethyl-1,2,2-trichlorovinylamine
acetone
N,N-dimethylamino-3,3-diethylacrylamide
Conditions | Yield |
---|---|
(i), (ii) /BRN= 635680/, (iii) (hydrolysis); Multistep reaction; |
2-methylallylmagnesium chloride
A
N,N-dimethylamino-3,3-diethylacrylamide
B
N,N-diethyl-3-methyl-3-butenamide
Conditions | Yield |
---|---|
In tetrahydrofuran; hexane at 20℃; for 1h; Yield given. Yields of byproduct given; | |
With lithium diisopropyl amide In tetrahydrofuran; hexane at 20℃; for 1h; Yield given. Yields of byproduct given; |
carbon monoxide
diethylamine
3-Chloro-2-methylpropene
A
diethyl-methallyl-amine
B
N,N-dimethylamino-3,3-diethylacrylamide
C
N,N-diethyl-3-methyl-3-butenamide
Conditions | Yield |
---|---|
With bis-triphenylphosphine-palladium(II) chloride In benzene under 76000 Torr; Ambient temperature; |
N,N-dimethylamino-3,3-diethylacrylamide
bis(pinacol)diborane
Conditions | Yield |
---|---|
With methanol; water; caesium carbonate; bis(1,5-cyclooctadiene)nickel (0); tricyclohexylphosphine In toluene at 20℃; for 7h; | 80% |
triethylsilyl chloride
N,N-dimethylamino-3,3-diethylacrylamide
A
(Z)-N,N-diethyl-3-methyl-4-triethylsilyl-but-2-enamide
B
(E)-N,N-diethyl-3-methyl-4-triethylsilyl-but-2-enamide
Conditions | Yield |
---|---|
Stage #1: N,N-dimethylamino-3,3-diethylacrylamide With lithium diisopropyl amide In tetrahydrofuran at -78 - -75℃; for 1h; Inert atmosphere; Stage #2: triethylsilyl chloride In tetrahydrofuran at -78℃; for 18.5h; Inert atmosphere; Reflux; Stage #3: With water; ammonium chloride In tetrahydrofuran Saturated solution; optical yield given as %de; diastereoselective reaction; | A 21% B 47% |
N,N-dimethylamino-3,3-diethylacrylamide
1-chloro-2,4-dimethoxybenzene
5,7-dimethoxy-2-methyl-4-naphthol
Conditions | Yield |
---|---|
With lithium cyclohexylisopropylamide In tetrahydrofuran -78 deg C, 1 h, rt; | 46% |
chloro-trimethyl-silane
N,N-dimethylamino-3,3-diethylacrylamide
A
(Z)-N,N-diethyl-3-methyl-4-trimethylsilyl-but-2-enamide
B
(E)-N,N-diethyl-3-methyl-4-trimethylsilyl-but-2-enamide
C
N,N-diethyl-3-methyl-3-butenamide
Conditions | Yield |
---|---|
Stage #1: N,N-dimethylamino-3,3-diethylacrylamide With lithium diisopropyl amide In tetrahydrofuran at -78 - -75℃; for 1h; Inert atmosphere; Stage #2: chloro-trimethyl-silane In tetrahydrofuran at -78℃; for 17.5h; Inert atmosphere; Reflux; Stage #3: With water; ammonium chloride In tetrahydrofuran Saturated solution; optical yield given as %de; diastereoselective reaction; | A 39% B 35% C n/a |
3-methoxyphenyl bromide
N,N-dimethylamino-3,3-diethylacrylamide
4-hydroxy-5-methoxy-2-methyl-naphthalene
Conditions | Yield |
---|---|
Stage #1: N,N-dimethylamino-3,3-diethylacrylamide With n-butyllithium; N-cyclohexylisopropylamine In tetrahydrofuran at -78℃; for 1h; Inert atmosphere; Stage #2: 3-methoxyphenyl bromide In tetrahydrofuran at 20℃; for 18h; Diels-Alder reaction; Inert atmosphere; | 35% |
With lithium cyclohexylisopropylamide 1) THF, hexane, -78 deg C, 1 h; 2) THF, -20 deg C, then room temp., overnight; Yield given. Multistep reaction; |
3,3-Dimethylacryloyl chloride
diethylamine
N,N-dimethylamino-3,3-diethylacrylamide
Conditions | Yield |
---|---|
90% | |
With diethyl ether |