Structure of Propargyl acrylate
CAS No.: 10477-47-1
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| CAS No. : | 10477-47-1 |
| Formula : | C6H6O2 |
| M.W : | 110.11 |
| SMILES Code : | O=C(OCC#C)C=C |
| English Name : | Prop-2-yn-1-yl acrylate |
| MDL No. : | MFCD00078451 |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 85% | With N,N,N',N'',N'''-pentamethyldiethylenetriamine; copper(I) bromide In N,N-dimethyl-formamide at 20℃; for 11h; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 95% | In N,N-dimethyl-formamide at 20℃; for 24h; | 1 Propargyl acrylate (13 g, 0.118 mmoles), dodecyl azide (22.3 g, 0.118 mmoles) and tetrakis(acetonitrile)copper (I) hexafluorophosphate (0.75 g, 2 mmoles) are dissolved in DMF (200 ml) and stirred at room temperature under nitrogen for 24 hours. The reaction mixture is poured into water wherefrom the product precipitated as a white crystalline solid (33.5 g; yield 95%; mp 50-520C). 1H NMR (CDCI3, δ ppm) 7.78 (broad, 1 H), 6.42 (d, 1 H), 6.16 (dd, 1 H), 5.82 (d, 1 H), 5.30 (s, 2H), 4.32 (t, 2H), 1.92 (t, 2H), 1.28 (m, 20H), 0.88 (t, 3H). 13C NMR (CDCI3, δ ppm) 165.7, 142.4, 131.1 , 127.9, 123.5, 57.6, 57.5, 50.2, 31.7, 30.1 , 29.4, 29.3, 29.2, 29.1 , 28.8, 26.3, 22.4, 13.9. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 93% | With bromotris(triphenylphosphine)copper(I); triethylamine In tetrahydrofuran at 60℃; for 5h; Inert atmosphere; | General reaction procedure for the click silylation General procedure: To a 50 ml two-necked round bottom flask with alkyne function (2 mmol), azide function (2 mmol/alkyne function), [CuBr(PPh3)3] (0.01 mmol/alkyne function), triethylamine (2 ml), and THF (2 ml) were added under nitrogen atmosphere and then the mixture was stirred at 60 °C for 5 h. The reaction mixture was allowed to cool, and the solvents were removed under vacuum followed by addition of hexane. The mixture was filtered and washed with 2×5 ml of hexane. The concentration of the filtrate under reduced pressure afforded the title compound in good to excellent yield. |
| 93% | With bromotris(triphenylphosphine)copper(I); triethylamine In tetrahydrofuran at 60℃; for 5h; Inert atmosphere; | General reaction procedure for the click silylation: General procedure: To a 50 ml two-necked round bottom flask with alkyne function (2 mmol), azide function (2 mmol/alkyne function), [CuBr(PPh3)3] (0.01 mmol/alkyne function), triethylamine (2 ml),and THF (2 ml) were added under nitrogen atmosphere and then the mixture was stirred at 60 °C for 5 h. The reaction mixture was allowed to cool, and the solvents were removed under vacuum followed by addition of hexane. The mixture was filtered and washed with 2 Χ 5 ml of hexane. The concentration ofthe filtrate under reduced pressure afforded the title compound in good to excellent yield. |
| With bromotris(triphenylphosphine)copper(I); triethylamine In tetrahydrofuran at 60℃; for 5h; Inert atmosphere; | General reaction procedure for the click silylation To a 50.0 ml two-necked round bottom flask with alkyne function (2 mmol), azide function (2 mmol/alkyne function), [CuBr(PPh3)3] (0.01 mmol/alkyne function), triethylamine (2.0 ml), and THF (2.0 ml) under nitrogen atmosphere and then the mixture was stirred at 60 °C for 5 h. The reaction mixture was allowed to cool, and the solvents were removed under vacuum followed by addition of hexane. The mixture was filtered and washed with 2 x 5.0 ml of hexane. The concentration of the filtrate under reduced pressure afforded the title compound in good to excellent yield. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 75% | With cesium fluoride In N,N-dimethyl-formamide at 110℃; for 2h; | General procedure for the synthesis of compounds 3a-d: General procedure: General procedure for the synthesis of compounds 3a-d: A mixture of correspondingly substituted 2,3,4,5-tetrahydro-1Hpyrido[4,3-b]indole 1a-d (2 mmol), 0.22 g (2 mmol) acrylicacid propyn-2-yl ester (2) and 0.1 g (0.66 mmol) of CsF in1 mL of DMF was stirred at 110 °C during 2 h. The solvent was removed in vacuo (~3 mmHg) and the product was extracted from the residue with CH2Cl2. The solvent was removed in vacuo and the residue was purified by column chromatography (MeOH/CHCl3 1:5). |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 63% | With 1,4-diaza-bicyclo[2.2.2]octane; In methanol; at 20℃; for 12h; | General procedure: To a flame-dried round bottle flask with a magnetic stirring bar were addedbipyridine aldehyde (0.001 mmol) 2 and (DABCO) as catalyst (10 mol%)) in methanol(4mL), followed by the addition of activated alkenes 4. The resulting mixture was stirred atroom temperature for 12 hours, after completion of the reaction (Monitored by TLC),solvents were removed in vacuo and the residue was purified on neutral alumina using 70%ethyl acetate in petroleum ether to afford the corresponding novel Morita-Baylis-Hillmanadduct of bipyridine 5 in very good yield. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 79% | With 1,4-diaza-bicyclo[2.2.2]octane In 1,4-dioxane; dichloromethane at 20℃; for 40h; | |
| 79% | With 1,4-diaza-bicyclo[2.2.2]octane In acetonitrile at 20℃; for 40h; | 25 Example 25 2-trifluoromethyl-methylthio-3- (4-nitro-phthalimide) - propionic acid propargyl N- trifluoromethylthio-4-nitro phthalimide (65.7mg, 0.225mmol), 1- propargyl acrylate (16.5mg, 0.15mmol), DABCO (8.75mg, 0.075mmol) and a mixed solution of methylene chloride and 1,4-dioxane: mixture (volume ratio 1 1,0.45mL) was stirred at room temperature for 40 hours.Concentrated under reduced pressure column chromatography to obtain the product isolated in 79% yield |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 62.9% | With aluminum oxide; potassium fluoride In N,N-dimethyl-formamide at 20℃; Green chemistry; | 4.1.2 Ethyl 3-(substituted)-6-methyl-4-(3-nitrophenyl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate (2a-j) General procedure: To a solution of DHPM (1) [31] (6.1g, 15mmol) and the appropriate substituted acrylate derivative (15mmol) in anhydrous DMF (30mL), KF/neutral alumina (10mol %) was added in one portion. The mixture was stirred at room temperature for 1-5 days. The completion of the reaction was monitored by TLC using 1:1 toluene: acetone. The catalyst was removed by filtration. The filtrate was then poured into ice-cold water (500mL). The obtained product was filtered, washed with water, dried and purified by crystallization or chromatography as specified under each compound. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 1: 20 % 2: 7 % | With 2-tert-butyl-1,1,3,3-tetramethylguanidine; scandium tris(trifluoromethanesulfonate) In dichloromethane at 40℃; Inert atmosphere; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 75 % | With 2-tert-butyl-1,1,3,3-tetramethylguanidine; scandium tris(trifluoromethanesulfonate) In dichloromethane at 40℃; Inert atmosphere; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 50 % | With DABSO In dichloromethane at 20℃; Inert atmosphere; UV-irradiation; |