ethyl (E)-4-hydroxy-3-methyl-2-butenoate
ethyl (E)-3-formyl-2-butenoate
Conditions | Yield |
---|---|
With manganese(IV) oxide In dichloromethane at 25℃; for 1h; | 92% |
With manganese(IV) oxide In dichloromethane for 3h; Ambient temperature; | 79% |
With manganese(IV) oxide; calcium sulfate In dichloromethane for 1h; Ambient temperature; | 72% |
ethyl (E/Z)-4,4-dimethoxy-3-methylbut-2-enoate
ethyl (E)-3-formyl-2-butenoate
Conditions | Yield |
---|---|
With hydrogenchloride In dichloromethane for 1.5h; | 78% |
With sulfuric acid In water | 70% |
With hydrogenchloride In 1,4-dioxane for 4h; Ambient temperature; | 53% |
(E)-4,4-Dimethoxy-3-methyl-crotonsaeureaethylester
ethyl (E)-3-formyl-2-butenoate
Conditions | Yield |
---|---|
With sodium acetate In water; acetic acid for 3.5h; Heating; | 69.8% |
With hydrogenchloride In dichloromethane; water at 0℃; for 2h; Inert atmosphere; |
ethyl (E)-4-bromo-3-methyl-2-butenoate
ethyl (E)-3-formyl-2-butenoate
Conditions | Yield |
---|---|
With sulfuric acid In water | 42% |
ethyl 2-ethoxyglycolate
propionaldehyde
ethyl (E)-3-formyl-2-butenoate
Conditions | Yield |
---|---|
With dibutylamine |
3-Methyl-4--crotonsaeureethylester
ethyl (E)-3-formyl-2-butenoate
Conditions | Yield |
---|---|
With sulfuric acid |
ethyl (E)-3-formyl-2-butenoate
Conditions | Yield |
---|---|
With manganese(IV) oxide; Petroleum ether |
diethoxyphosphoryl-acetic acid ethyl ester
Pyruvic aldehyde dimethyl acetal
ethyl (E)-3-formyl-2-butenoate
Conditions | Yield |
---|---|
Stage #1: diethoxyphosphoryl-acetic acid ethyl ester; Pyruvic aldehyde dimethyl acetal With sodium hydride In N,N-dimethyl-formamide at 0℃; for 1h; Stage #2: With hydrogenchloride; water In dichloromethane at 20℃; for 3h; |
ethyl 3-methylbut-2-enoate
ethyl (E)-3-formyl-2-butenoate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 90 percent / SeO2 / aq. ethanol / 24 h / Heating 2: 72 percent / CaSO4, MnO2 / CH2Cl2 / 1 h / Ambient temperature View Scheme | |
Multi-step reaction with 2 steps 1: N-bromosuccinimide, d'acide m-chloroperbenzoique / CCl4 2: 42 percent / H2SO4 / H2O View Scheme | |
Multi-step reaction with 3 steps 1: Br2 2: (i) Py, (ii) /BRN= 607293/, NaOH 3: aq. H2SO4 View Scheme |
β,γ-epoxy-isovaleric acid ethyl ester
ethyl (E)-3-formyl-2-butenoate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: hexamethylphosphoric amide / 2 h / Ambient temperature 2: 79 percent / activated MnO2 / CH2Cl2 / 3 h / Ambient temperature View Scheme |
ethyl 4-bromo-3-methylcrotonate
ethyl (E)-3-formyl-2-butenoate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: (i) Py, (ii) /BRN= 607293/, NaOH 2: aq. H2SO4 View Scheme |
diethyl (2R,3R)-tartrate
2-(triphenylphosphoranylidene)propionaldehyde
ethyl (E)-3-formyl-2-butenoate
Conditions | Yield |
---|---|
With NaIO4 on SiO2 In dichloromethane at 20℃; |
ethyl (E)-3-formyl-2-butenoate
acetic anhydride
(E)-ethyl 3-methyl-4-diacetoxycrotonate
Conditions | Yield |
---|---|
With iron(III) chloride at 0℃; for 0.5h; | 99% |
ethyl (E)-3-formyl-2-butenoate
ethyl (E)-4-hydroxy-3-methyl-2-butenoate
Conditions | Yield |
---|---|
With sodium tetrahydroborate In methanol at 0 - 20℃; | 98% |
With sodium tetrahydroborate In methanol at 0 - 20℃; for 16h; chemoselective reaction; | 90% |
With sodium tetrahydroborate In ethanol for 0.25h; | 3.9 g |
ethyl (E)-3-formyl-2-butenoate
ethylene glycol
ethyl (E)-4,4-ethylenedioxy-3-methylbut-2-enoate
Conditions | Yield |
---|---|
With pyridinium p-toluenesulfonate In benzene for 4h; Heating; | 91% |
With pyridinium p-toluenesulfonate | 89% |
With pyridinium p-toluenesulfonate In benzene for 12h; Heating; |
ethyl (E)-3-formyl-2-butenoate
(7E)-9-ethynyl-β-ionol
ethyl 9-(2',6',6'-trimethyl-1'-cyclohexen-1'-yl)-3,7-dimethyl-4,7-dihydroxy-(2E,8E)-nona-2,8-dien-5-ynoate
Conditions | Yield |
---|---|
With ethylmagnesium bromide | 90% |
With ethylmagnesium bromide 1.) THF, room temperature, 1 h, 2.) THF, 15 min; Yield given. Multistep reaction; |
ethyl (E)-3-formyl-2-butenoate
(3,7-dimethyl-2,6-octadienyl)-triphenylphosphonium bromide
ethyl (2E,4E,6E)-3,7,11-trimethyldodeca-2,4,6,10-tetraenoate
Conditions | Yield |
---|---|
With n-butyllithium In tetrahydrofuran at 20℃; Condensation; Wittig reaction; | 90% |
ethyl (E)-3-formyl-2-butenoate
Conditions | Yield |
---|---|
With trimethylsilyl trifluoromethanesulfonate In dichloromethane at -20℃; for 1.5h; Inert atmosphere; diastereoselective reaction; | 90% |
ethyl (E)-3-formyl-2-butenoate
Methyltriphenylphosphonium bromide
methyl-3 pentadiene-2,4 oate d'ethyle E
Conditions | Yield |
---|---|
Stage #1: Methyltriphenylphosphonium bromide With n-butyllithium In tetrahydrofuran; hexane at -78 - 0℃; for 1h; Schlenk technique; Stage #2: ethyl (E)-3-formyl-2-butenoate In tetrahydrofuran; hexane at 0℃; for 0.5h; Schlenk technique; | 89% |
Stage #1: Methyltriphenylphosphonium bromide With n-butyllithium In tetrahydrofuran; hexane at -78 - 0℃; Wittig reaction; Stage #2: ethyl (E)-3-formyl-2-butenoate In tetrahydrofuran; hexane at -78 - 20℃; Wittig reaction; | 83% |
Stage #1: Methyltriphenylphosphonium bromide With n-butyllithium In tetrahydrofuran; hexane at -78 - 0℃; for 1h; Stage #2: ethyl (E)-3-formyl-2-butenoate In tetrahydrofuran; hexane at -78 - 20℃; for 10h; | 40% |
Stage #1: Methyltriphenylphosphonium bromide With n-butyllithium In tetrahydrofuran; hexane at -78 - 110℃; Inert atmosphere; Stage #2: ethyl (E)-3-formyl-2-butenoate In tetrahydrofuran; hexane at -45℃; Inert atmosphere; |
ethyl (E)-3-formyl-2-butenoate
1-bromo-2-ethyl-3,4-dimethoxybenzene
Conditions | Yield |
---|---|
Stage #1: 1-bromo-2-ethyl-3,4-dimethoxybenzene With ethyl bromide; iodine; magnesium In tetrahydrofuran for 1h; Reflux; Stage #2: ethyl (E)-3-formyl-2-butenoate In tetrahydrofuran at 0 - 20℃; for 12h; Stage #3: With hydrogenchloride In tetrahydrofuran; water | 89% |
ethyl (E)-3-formyl-2-butenoate
(5Z,7E)-(1S,3R)-1,3-bis[(t-butyldimethyl-silyl)oxy]-24-phenylsulfonyl-22,23-dinor-9,10-secochola-5,7,10(19)-triene
ethyl (5Z,7E,23aE)-(1S,3R)-1,3-bis[(t-butyldimethylsilyl)oxy]-22-phenylsulfonyl-23-hydroxy-23a-methyl-23a,23b-dihomo-9,10-secochola-5,7,10(19),23-tetraene-24-oate
Conditions | Yield |
---|---|
With n-butyllithium In tetrahydrofuran at -70℃; for 0.25h; | 88% |
ethyl (E)-3-formyl-2-butenoate
4-methoxyphenylhydrazine hydrochloride
Conditions | Yield |
---|---|
With pyridine at 20℃; for 0.5h; | 87% |
ethyl (E)-3-formyl-2-butenoate
hex-1-yne
Conditions | Yield |
---|---|
Stage #1: hex-1-yne With n-butyllithium In tetrahydrofuran; hexane for 1h; Inert atmosphere; Cooling with acetone-dry ice; Stage #2: ethyl (E)-3-formyl-2-butenoate In tetrahydrofuran; hexane at 20℃; Inert atmosphere; | 86% |
Conditions | Yield |
---|---|
With lithium hexamethyldisilazane Julia Olefin Synthesis; | 85% |
Conditions | Yield |
---|---|
With titanium(IV) tetraethanolate In dichloromethane for 6h; Inert atmosphere; Reflux; | 84% |
ethyl (E)-3-formyl-2-butenoate
[(2E,4E)-5-(2-Acetoxymethyl-6,6-dimethyl-cyclohex-1-enyl)-3-methyl-penta-2,4-dienyl]-triphenyl-phosphonium; bromide
A
(2E,4E,6E,8E)-9-(2-Hydroxymethyl-6,6-dimethyl-cyclohex-1-enyl)-3,7-dimethyl-nona-2,4,6,8-tetraenoic acid ethyl ester
B
(2E,4Z,6E,8E)-9-(2-Acetoxymethyl-6,6-dimethyl-cyclohex-1-enyl)-3,7-dimethyl-nona-2,4,6,8-tetraenoic acid ethyl ester
C
ethyl (2E,4E,6E,8E)-9-<2-(acetoxymethyl)-6,6-dimethyl-1-cyclohexen-1-yl>-3,7-dimethyl-2,4,6,8-nonatetraenoate
Conditions | Yield |
---|---|
With sodium methylate In methanol; dichloromethane at 0 - 5℃; for 0.166667h; | A n/a B n/a C 81% |
ethyl (E)-3-formyl-2-butenoate
acetone
Conditions | Yield |
---|---|
With chiral binaphthyl-based amino acid In N,N-dimethyl-formamide at 20℃; for 24h; | 81% |
ethyl (E)-3-formyl-2-butenoate
(2S)-ethoxy-(4S)-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydro-2H-pyran
ethyl-(2E,4R)-4-[(2R,6S)-6-ethoxy-5,6-dihydro-2H-pyran-2-yl]-4-hydroxy-3-methylbut-2-enoate
Conditions | Yield |
---|---|
Stage #1: ethyl (E)-3-formyl-2-butenoate; (2S)-ethoxy-(4S)-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydro-2H-pyran at 50℃; for 5h; Inert atmosphere; Stage #2: With water; sodium hydrogencarbonate for 0.5h; Inert atmosphere; Saturated solution; | 81% |
at 25℃; for 24h; | 476 mg |
ethyl (E)-3-formyl-2-butenoate
1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalenyl)ethanone
ethyl (E)-4-hydroxy-3-methyl-6-oxo-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthalenyl)-2-hexenoate
Conditions | Yield |
---|---|
With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane | 80% |
With n-butyllithium; diisopropylamine 1.) THF, hexane, -78 deg C, 20 min, 2.) THF, hexane, -78 deg C, 35 min; Yield given. Multistep reaction; |
ethyl (E)-3-formyl-2-butenoate
(triphenylphosphoranylidene)acetaldehyde
ethyl (2E,4E)-3-methyl-6-oxo-2,4-hexadienoate
Conditions | Yield |
---|---|
In dichloromethane at 20℃; for 15h; Wittig reaction; | 80% |
In dichloromethane at 20℃; for 15h; optical yield given as %de; | 80% |
In dichloromethane at 20℃; for 14h; Wittig reaction; | 68% |
In dichloromethane at 20℃; for 15h; Inert atmosphere; |
ethyl (E)-3-formyl-2-butenoate
(triphenylphosphoranylidene)acetaldehyde
A
ethyl (2E,4E)-3-methyl-6-oxo-2,4-hexadienoate
B
C11H14O3
Conditions | Yield |
---|---|
In dichloromethane at 20℃; for 15h; Wittig reaction; stereoselective reaction; | A 80% B 2.7% |
Conditions | Yield |
---|---|
A n/a B 76% |
ethyl (E)-3-formyl-2-butenoate
(E)-(R)-4-[(2R,5R,6S)-6-Ethoxy-5-(3-methyl-but-2-enyl)-5,6-dihydro-2H-pyran-2-yl]-4-hydroxy-3-methyl-but-2-enoic acid ethyl ester
Conditions | Yield |
---|---|
at 110℃; for 48h; | 76% |
ethyl (E)-3-formyl-2-butenoate
Conditions | Yield |
---|---|
Stage #1: triphenyl-(2,3,3-trimethyl-cyclohex-1-enylmethyl)-phosphonium; iodide With n-butyllithium In tetrahydrofuran; hexane at -10℃; for 0.25h; Wittig reaction; Stage #2: ethyl (E)-3-formyl-2-butenoate In tetrahydrofuran; hexane at -10℃; for 5h; Wittig reaction; Stage #3: With hydrogenchloride In tetrahydrofuran; hexane | 75% |
ethyl (E)-3-formyl-2-butenoate
Dimethyl-(3-methyl-but-2-enyl)-sulfonium; chloride
(E)-3-[3-(2-Methyl-propenyl)-oxiranyl]-but-2-enoic acid ethyl ester
Conditions | Yield |
---|---|
With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride In dichloromethane at 0℃; for 0.333333h; | 74% |
ethyl (E)-3-formyl-2-butenoate
(2S,3R,4R)-2-Ethoxy-3-heptyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,4-dihydro-2H-pyran
ethyl-(2E,4R)-4-[(2R,5R,6S)-6-ethoxy-5-heptyl-5,6-dihydro-2H-pyran-2-yl]-4-hydroxy-3-methylbut-2-enoate
Conditions | Yield |
---|---|
at 110℃; for 48h; | 74% |
ethyl (E)-3-formyl-2-butenoate
N,N-diisopropylhydrazine
Conditions | Yield |
---|---|
With magnesium sulfate In dichloromethane at 23℃; for 24h; Inert atmosphere; | 74% |
ethyl (E)-3-formyl-2-butenoate
1,1-dimethylhydrazine
Conditions | Yield |
---|---|
With magnesium sulfate In dichloromethane at 23℃; for 24h; Inert atmosphere; | 74% |
2,5,5-trimethylpyrroline N-oxide
ethyl (E)-3-formyl-2-butenoate
Conditions | Yield |
---|---|
In toluene at 110℃; for 3h; | 72% |
The CAS register number of Ethyl 3-methyl-4-oxocrotonate is 62054-49-3. It also can be called as ethyl trans-γ-oxosenecioate and the systematic name about this chemical is ethyl (2E)-3-methyl-4-oxobut-2-enoate. The molecular formula about this chemical is C7H10O3 and the molecular weight is 142.15.
Physical properties about Ethyl 3-methyl-4-oxocrotonate are: (1)ACD/LogP: 0.55; (2)ACD/LogD (pH 5.5): 0.55; (3)ACD/LogD (pH 7.4): 0.55; (4)ACD/BCF (pH 5.5): 1.54; (5)ACD/BCF (pH 7.4): 1.54; (6)ACD/KOC (pH 5.5): 47.48; (7)ACD/KOC (pH 7.4): 47.48; (8)#H bond acceptors: 3; (9)#Freely Rotating Bonds: 4; (10)Polar Surface Area: 43.37 Å2; (11)Index of Refraction: 1.438; (12)Molar Refractivity: 36.34 cm3; (13)Molar Volume: 138.2 cm3; (14)Polarizability: 14.4x10-24cm3; (15)Surface Tension: 31.5 dyne/cm; (16)Density: 1.027 g/cm3; (17)Flash Point: 87.4 °C; (18)Enthalpy of Vaporization: 45.3 kJ/mol; (19)Boiling Point: 216.7 °C at 760 mmHg; (20)Vapour Pressure: 0.138 mmHg at 25 °C.
When you are using this chemical, please be cautious about it as the following:
This chemical is irritating to eyes, respiratory system and skin. It may cause inflammation to the skin or other mucous membranes. If you want to use this chemical, wear suitable protective clothing. When you are using it, do not breathe vapour and avoid contact with skin and eyes. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
You can still convert the following datas into molecular structure:
(1)SMILES: O=C\C(=C\C(=O)OCC)C
(2)InChI: InChI=1/C7H10O3/c1-3-10-7(9)4-6(2)5-8/h4-5H,3H2,1-2H3/b6-4+
(3)InChIKey: YLFXEUMFBVGYEL-GQCTYLIABJ
(4)Std. InChI: InChI=1S/C7H10O3/c1-3-10-7(9)4-6(2)5-8/h4-5H,3H2,1-2H3/b6-4+
(5)Std. InChIKey: YLFXEUMFBVGYEL-GQCTYLIASA-N
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