Conditions | Yield |
---|---|
With [1-(3-sulfonic acid)]propyl-3-methylimidazolium hydrogen sulfate for 3h; Reflux; Green chemistry; | 97.8% |
With sulfuric acid | 95% |
With sulfuric acid for 16h; Heating; | 92% |
tert-butyl(1-methoxyvinyl)dimethylsilane
acetone
Methyl 3,3-dimethylacrylate
Conditions | Yield |
---|---|
Stage #1: tert-butyl(1-methoxyvinyl)dimethylsilane; acetone With C40H61Al3O3 In acetonitrile at 0 - 5℃; for 72h; Mukaiyama Aldol Addition; Stage #2: With hydrogenchloride In water; acetonitrile at 20℃; for 3h; Mukaiyama Aldol Addition; | 90% |
methanol
C9H18ClNO3
A
Methyl 3,3-dimethylacrylate
B
β-(N-methoxy-N-isopropoxyamino)-isovaleric acid methyl ester
Conditions | Yield |
---|---|
With triethylamine 1.) -20 deg C, 6 h, 2.) 20 deg C, 1 h; | A 14% B 86% |
(E)-4-bromo-3-methyl-2-butenoic acid methyl ester
A
Methyl 3,3-dimethylacrylate
B
(E)-5-Isopropenyl-3-methyl-hex-2-enedioic acid dimethyl ester
Conditions | Yield |
---|---|
With zinc In dimethyl sulfoxide for 4h; | A 10% B 68% |
(Z)-methyl-β-bromomethyl-β-methylacrylate
A
Methyl 3,3-dimethylacrylate
B
(Z)-5-Isopropenyl-3-methyl-hex-2-enedioic acid dimethyl ester
Conditions | Yield |
---|---|
With zinc In dimethyl sulfoxide for 4h; | A 10% B 67% |
β-(N-chloro-N-methoxyamino)-isovaleric acid methyl ester
isobutene
A
Methyl 3,3-dimethylacrylate
B
β-isovaleric acid methyl ester
Conditions | Yield |
---|---|
With sulfur dioxide 1.) 7 deg C, 24 h, 2.) 20 deg C, 2 h; | A 13% B 67% |
2,2,3,3-tetracyano-4,4-dimethylcyclopentanone dimethyl acetal
A
Methyl 3,3-dimethylacrylate
B
methyl 3,3-dimethyl-4,5,5-tricyano-4-pentenoate
C
methyl 3,3-dimethyl-4,4,5,5-tetracyanopentanoate
Conditions | Yield |
---|---|
With water In acetonitrile at 80℃; for 12h; | A n/a B n/a C 63% |
(2-Trifluoromethanesulfonyl-pentane-2-sulfonyl)-acetic acid methyl ester
Methyl 3,3-dimethylacrylate
Conditions | Yield |
---|---|
With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate In dichloromethane; water | 62% |
β-(N,N-dimethoxyamino)-isovaleric acid methyl ester
A
Methyl 3,3-dimethylacrylate
B
3-(2-Methoxycarbonyl-1,1-dimethyl-ethyl-NNO-azoxy)-3-methyl-butyric acid methyl ester
Conditions | Yield |
---|---|
With triethylamine hydrochloride In chloroform for 126h; Product distribution; Heating; various acyclic N,N-dialkoxyamines; | A 15% B 51.9% |
methyl 2-diazo-3-methylbutanoate
Methyl 3,3-dimethylacrylate
Conditions | Yield |
---|---|
at 400℃; under 0.001 - 0.1 Torr; | 47% |
methanol
4,4-dimethyl-2-(2-propylidene)-3-thietanone
A
Methyl 3,3-dimethylacrylate
B
4-Isopropylidene-5-methoxy-2,2-dimethyl-[1,3]oxathiolane
Conditions | Yield |
---|---|
In methanol for 3h; Irradiation; | A 28% B 22% |
3-diazo-2,2,5,5-tetramethylthiolan-4-one
A
Methyl 3,3-dimethylacrylate
B
2,2,4,4-Tetramethyl-thietane-3-carboxylic acid methyl ester
C
4-Isopropylidene-5-methoxy-2,2-dimethyl-[1,3]oxathiolane
Conditions | Yield |
---|---|
In methanol Irradiation; | A 19% B 28% C 14% |
4,4-dimethyl-2-(2-propylidene)-3-thietanone
A
Methyl 3,3-dimethylacrylate
B
4-Isopropylidene-5-methoxy-2,2-dimethyl-[1,3]oxathiolane
Conditions | Yield |
---|---|
In methanol Irradiation; | A 28% B 22% |
methanol
A
Methyl 3,3-dimethylacrylate
B
2,2,4,4-Tetramethyl-thietane-3-carboxylic acid methyl ester
C
4-Isopropylidene-5-methoxy-2,2-dimethyl-[1,3]oxathiolane
Conditions | Yield |
---|---|
Irradiation; | A 19% B 27.8% C 14% |
β-(N-chloro-N-methoxyamino)-isovaleric acid methyl ester
acetonitrile
A
Methyl 3,3-dimethylacrylate
B
methyl β-(Nacetylamino)isovalerate
Conditions | Yield |
---|---|
With silver fluoride at -78℃; for 15h; | A n/a B 27.8% |
methyl 2-bromo-3-methylbutanoic ester
A
2-pyrrolidinon
B
Methyl 3,3-dimethylacrylate
C
trimethylsilyl bromide
Conditions | Yield |
---|---|
With N-trimethylsilyl-pyrrolidin-2-one at 165 - 195℃; for 3h; Yields of byproduct given; | A n/a B 27% C n/a |
methyl (2,2-dimethyl-3-oxocyclobutyl)acetate
A
Methyl 3,3-dimethylacrylate
B
methyl 2-(2,2-dimethyl-5-oxotetrahydrofuran-3-yl)acetate
C
Methyl 2,2-dimethyl-4,5-dihydro-3-furanacetate
D
Methyl 2,2-dimethyl-5-(2,2-dimethyltetrahydro-3-(methoxycarbonyl)furan-5-ylidene)tetrahydro-3-furanacetate
Conditions | Yield |
---|---|
With 4 A molecular sieve In dichloromethane for 72h; Irradiation; Further byproducts given; | A 16% B n/a C 12% D 22% |
Conditions | Yield |
---|---|
With 1,8-diazabicyclo[5.4.0]undec-7-ene In benzonitrile; acetonitrile at 20℃; for 5h; | 22% |
A
Methyl 3,3-dimethylacrylate
B
methylammonium carbonate
Conditions | Yield |
---|---|
bei der Destillation im Vakuum ueber eine rotgluehende Platinspirale; |
diethyl ether
3,4-Dibromo-3-methyl-butan-2-one
sodium methylate
A
Methyl 3,3-dimethylacrylate
B
β-methoxy-isovaleric acid methyl ester
methyl 3-methyl-3-butenoate
sodium methylate
A
Methyl 3,3-dimethylacrylate
B
β-methoxy-isovaleric acid methyl ester
Conditions | Yield |
---|---|
With diethyl ether |
3,4-Dibromo-3-methyl-butan-2-one
sodium methylate
A
Methyl 3,3-dimethylacrylate
B
β-methoxy-isovaleric acid methyl ester
Conditions | Yield |
---|---|
With diethyl ether anfangs unter Kuehlung; | |
With diethyl ether |
methyl 2-bromo-3-methylbutanoic ester
Methyl 3,3-dimethylacrylate
Conditions | Yield |
---|---|
With N,N-diethylaniline |
methanol
ethyl 2-acetyl-3-methylbut-2-enoate
methyl iodide
Methyl 3,3-dimethylacrylate
Conditions | Yield |
---|---|
With sodium methylate |
Conditions | Yield |
---|---|
at -196.1℃; |
methanol
methyl (2,2-dimethyl-3-oxocyclobutyl)acetate
A
Methyl 3,3-dimethylacrylate
B
(2,2-Dimethyl-cyclopropyl)-essigsaeuremethylester
Methyl (3R*,5S*)-5-methoxy-2,2-dimethyltetrahydro-3-furanacetate
Methyl (3R*,5R*)-5-methoxy-2,2-dimethyltetrahydro-3-furanacetate
Conditions | Yield |
---|---|
for 16h; Irradiation; Yield given. Yields of byproduct given; |
3-methyl-but-2-enal dimethyl acetal
A
Methyl 3,3-dimethylacrylate
B
3,3-dimethyl acrylaldehyde
C
3-Dimethoxymethyl-2,2-dimethyl-oxirane
Conditions | Yield |
---|---|
With potassium fluoride; sodium fluoride; 3-chloro-benzenecarboperoxoic acid In dichloromethane 1.) 15 h, RT; 2.) 1 h, RT; |
β,β-Di(3>methyl)acrylsaeure-methylester
Methyl 3,3-dimethylacrylate
Conditions | Yield |
---|---|
With potassium hydroxide In methanol |
methyl tert-butyl(pivaloyl)acetate
A
Methyl 3,3-dimethylacrylate
B
methyl 3,3-dimethylbutyrate
Conditions | Yield |
---|---|
at 900℃; under 8E-05 Torr; Product distribution; |
methyl tert-butyl(pivaloyl)acetate
A
Methyl 3,3-dimethylacrylate
B
methyl 3,3-dimethylbutyrate
C
Methyl 4,4-dimethyl-3-oxopentanoate
D
isobutene
E
malonic acid dimethyl ester
Conditions | Yield |
---|---|
at 600℃; under 8E-05 Torr; Product distribution; other temperatures; |
Methyl 3,3-dimethylacrylate
nonylmagnesium bromide
Conditions | Yield |
---|---|
With copper(l) iodide; chloro-trimethyl-silane In tetrahydrofuran; diethyl ether at -15 - 20℃; | 100% |
With chloro-trimethyl-silane; copper(l) iodide In tetrahydrofuran at -15 - 20℃; | |
With copper(l) iodide; chloro-trimethyl-silane In tetrahydrofuran at -15 - 20℃; |
Methyl 3,3-dimethylacrylate
5,5-dimethylpyrazolidin-3-one
Conditions | Yield |
---|---|
With hydrazine hydrate In ethanol at 20℃; for 5h; Reflux; | 99% |
Conditions | Yield |
---|---|
Stage #1: Methyl 3,3-dimethylacrylate With piperidine; N-benzyl-trimethylammonium hydroxide In methanol at 0℃; Inert atmosphere; Stage #2: Methyl 3-mercaptopropionate at 60℃; for 24h; Inert atmosphere; | 97.23% |
With piperidine; N-benzyl-trimethylammonium hydroxide In methanol at 0 - 60℃; for 24h; Inert atmosphere; | 97% |
With piperidine; N-benzyl-trimethylammonium hydroxide In methanol at 60℃; for 24h; Michael addition; | 75% |
Methyl 3,3-dimethylacrylate
3,5-Dimethylphenol
4,4,5,7-tetramethyl-3,4-dihydrocoumarin
Conditions | Yield |
---|---|
With methanesulfonic acid at 70℃; for 6h; | 96% |
With sulfuric acid Michael Addition; Reflux; | 93% |
With methanesulfonic acid at 20 - 70℃; for 17h; | 92% |
Methyl 3,3-dimethylacrylate
tert-butylhydrazine
Conditions | Yield |
---|---|
In Dimethyl ether for 168h; | 96% |
Conditions | Yield |
---|---|
With ammonium cerium (IV) nitrate; iodine at 50℃; for 15h; | 96% |
Conditions | Yield |
---|---|
With methanesulfonic acid at 70℃; | 96% |
Methyl 3,3-dimethylacrylate
n-decyl magnesium bromide
Conditions | Yield |
---|---|
With copper(l) iodide; chloro-trimethyl-silane In tetrahydrofuran; 2-methyltetrahydrofuran at -15 - 20℃; Inert atmosphere; | 96% |
Methyl 3,3-dimethylacrylate
isononanoyl chloride
Conditions | Yield |
---|---|
With aluminum (III) chloride; tin(IV) chloride at 40℃; for 5h; Time; Cooling with ice; Reflux; | 95.4% |
Stage #1: isononanoyl chloride With aluminum (III) chloride In dichloromethane at 30℃; for 0.666667h; Stage #2: Methyl 3,3-dimethylacrylate In dichloromethane at 38℃; for 1h; Temperature; | |
Stage #1: isononanoyl chloride With aluminum (III) chloride In dichloromethane for 5h; Stage #2: Methyl 3,3-dimethylacrylate In dichloromethane at 40℃; for 10h; Time; | |
Stage #1: isononanoyl chloride With anhydrous aluminum chloride, anhydrous lanthanum chloride, anhydrous lithium perchlorate on silica gel catalyst In dichloromethane at 0℃; for 1h; Stage #2: Methyl 3,3-dimethylacrylate In dichloromethane at 25 - 40℃; for 11h; Temperature; |
Methyl 3,3-dimethylacrylate
(+/-)-lavandulol
A
2-isopropenyl-5-methyl-4-hexen-1-yl 3-methyl-2-butenoate
Conditions | Yield |
---|---|
With titanium(IV) isopropylate In toluene at 100℃; Temperature; Reagent/catalyst; | A 94.9% B n/a |
Methyl 3,3-dimethylacrylate
2,3-dibromo-3-metyl-butenoate
Conditions | Yield |
---|---|
With bromine In dichloromethane at 0℃; for 0.25h; Inert atmosphere; Schlenk technique; | 94% |
With bromine In dichloromethane at 0℃; for 10h; | 73% |
With tetrachloromethane; bromine | |
With bromine | |
With bromine In neat (no solvent) for 48h; from -50 deg C to -70 deg C; |
Methyl 3,3-dimethylacrylate
2,4-Xylenol
4,4,6,8-tetramethyldihydrocoumarin
Conditions | Yield |
---|---|
With methanesulfonic acid at 70℃; Condensation; cyclization; | 93% |
Methyl 3,3-dimethylacrylate
allyl bromide
2-(prop-1-en-2-yl)pent-4-en-1-ol
Conditions | Yield |
---|---|
Stage #1: Methyl 3,3-dimethylacrylate With n-butyllithium; diisopropylamine In tetrahydrofuran at -78 - 0℃; for 1.83333h; Inert atmosphere; Cooling with acetone-dry ice; Stage #2: allyl bromide In tetrahydrofuran at -78 - 0℃; for 15h; Inert atmosphere; Cooling with acetone-dry ice; Stage #3: With lithium aluminium tetrahydride In tetrahydrofuran for 3h; Inert atmosphere; | 93% |
Stage #1: Methyl 3,3-dimethylacrylate; allyl bromide With lithium diisopropyl amide Inert atmosphere; Stage #2: With lithium aluminium tetrahydride Inert atmosphere; | 93% |
Methyl 3,3-dimethylacrylate
Conditions | Yield |
---|---|
With ammonium cerium (IV) nitrate; water; iodine In acetonitrile at 50℃; for 9h; Reagent/catalyst; | 93% |
Conditions | Yield |
---|---|
With zinc copper In methanol for 24h; Heating; | 88% |
With magnesium In methanol at 10℃; for 2.5h; | 78% |
With platinum(IV) oxide Hydrogenation; |
Conditions | Yield |
---|---|
In diethyl ether at 0℃; for 1h; | 88% |
Methyl 3,3-dimethylacrylate
Trimethylhydroquinone
6-hydroxy-4,4,5,7,8-pentamethyl-3,4-dihydrocoumarin
Conditions | Yield |
---|---|
With methanesulfonic acid | 87% |
With methanesulfonic acid at 70℃; for 3h; | 81.2% |
With methanesulfonic acid at 70℃; for 2h; | 80% |
Methyl 3,3-dimethylacrylate
tert-butyldimethylsilyl chloride
Conditions | Yield |
---|---|
With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; n-butyllithium; diisopropylamine In tetrahydrofuran at -78 - 20℃; for 1.5h; | 87% |
Methyl 3,3-dimethylacrylate
methyl 3-amino-3-methyl-butanoate
Conditions | Yield |
---|---|
With ammonia In methanol at 120℃; for 4h; Inert atmosphere; Microwave irradiation; | 87% |
Methyl 3,3-dimethylacrylate
<(phenylsuilfonyl)methylene>dilithium
1-benzenesulfonyl-4-methylpent-3-en-2-one
Conditions | Yield |
---|---|
86% |
Conditions | Yield |
---|---|
With magnesium In tetrahydrofuran Heating; | 86% |
Methyl 3,3-dimethylacrylate
Conditions | Yield |
---|---|
With lithium aluminium deuteride at 20℃; for 2h; | 86% |
Conditions | Yield |
---|---|
With lithium aluminium deuteride | 86% |
With lithium aluminium deuteride In diethyl ether at 0℃; for 1h; Inert atmosphere; Reflux; | 76% |
Methyl 3,3-dimethylacrylate
Conditions | Yield |
---|---|
Stage #1: (R)-1-methyl-4-(1-(phenylsulfonyl)propan-2-yl)benzene With n-butyllithium In tetrahydrofuran at -78 - -50℃; Inert atmosphere; Glovebox; Schlenk technique; Stage #2: With magnesium bromide ethyl etherate In tetrahydrofuran at -78 - 20℃; for 0h; Inert atmosphere; Glovebox; Schlenk technique; Stage #3: Methyl 3,3-dimethylacrylate In tetrahydrofuran at -78 - 20℃; Inert atmosphere; Glovebox; Schlenk technique; | 85% |
Stage #1: (R)-1-methyl-4-(1-(phenylsulfonyl)propan-2-yl)benzene With n-butyllithium In tetrahydrofuran; hexane at -50℃; Inert atmosphere; Stage #2: With magnesium bromide ethyl etherate In tetrahydrofuran; diethyl ether; hexane at -78 - 0℃; for 0.166667h; Inert atmosphere; Stage #3: Methyl 3,3-dimethylacrylate In tetrahydrofuran; diethyl ether; hexane at -78 - 20℃; Inert atmosphere; enantioselective reaction; | 77% |
Methyl 3,3-dimethylacrylate
7-methyl-3-methylene-7-octen-1-ol
Conditions | Yield |
---|---|
With titanium(IV) isopropylate Inert atmosphere; Heating; | 84.7% |
Methyl 3,3-dimethylacrylate
Conditions | Yield |
---|---|
Stage #1: (4-(tert-butyldimethylsilyloxy)butyl)magnesium chloride With zirconocene dichloride In tetrahydrofuran; toluene at 0℃; for 3h; Stage #2: Methyl 3,3-dimethylacrylate In tetrahydrofuran; toluene at 0 - 20℃; | 84% |
piperazine
Methyl 3,3-dimethylacrylate
dimethyl 3,3'-(piperazine-1,4-diyl)bis-(3-methylbutanoate)
Conditions | Yield |
---|---|
In tetrahydrofuran; methanol at 20℃; for 24h; Aza-Michael addition; hyperbaric; | 84% |
Molecular Structure of Methyl 3-methyl-2-butenoate (CAS NO.924-50-5):
IUPAC Name: methyl 3-methylbut-2-enoate
Empirical Formula: C6H10O2
Molecular Weight: 114.1424
H bond acceptors: 2
H bond donors: 0
Freely Rotating Bonds: 2
Polar Surface Area: 26.3Å2
Index of Refraction: 1.42
Molar Refractivity: 31.52 cm3
Molar Volume: 124.4 cm3
Surface Tension: 25.2 dyne/cm
Density: 0.916 g/cm3
Flash Point: 32.1 °C
Enthalpy of Vaporization: 37.39 kJ/mol
Boiling Point: 136.5 °C at 760 mmHg
Vapour Pressure: 7.36 mmHg at 25°C
Melting point: -41°C
InChI
InChI=1/C6H10O2/c1-5(2)4-6(7)8-3/h4H,1-3H3
Smiles
C(\C=C(\C)C)(OC)=O
EINECS: 213-107-4
Product Categories: (intermediate of Gancyclovir)
Hazard Codes: Xi
Risk Statements: 10
R10:Flammable.
Safety Statements: 16-29-33
S16:Keep away from sources of ignition.
S29:Do not empty into drains.
S33:Take precautionary measures against static discharges.
RIDADR: UN 3272 3/PG 3
WGK Germany: 1
F: 8
Hazard Note: Irritant
HazardClass: 3
PackingGroup: III
Methyl 3-methyl-2-butenoate , with CAS number of 924-50-5, can be called Senecioic acid, methyl ester (6CI) ; 3-Methyl-2-butenoic acid methyl ester ; 3-Methylcrotonic acid methyl ester ; Methyl 3,3-dimethacrylate ; Methyl 3,3-dimethylacrylate ; Methyl b,b-dimethylacrylate .
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