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Excepted Quantity | USD 0.00 |
Limited Quantity | USD 15-60 |
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Purity | Size | Price | VIP Price | USA Stock *0-1 Day | Global Stock *5-7 Days | Quantity | |||||
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* Storage: {[proInfo.prStorage]}
CAS No. : | 66086-33-7 | MDL No. : | MFCD00008808 |
Formula : | C12H18O4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | FBCRUXRGQFLOMC-UHFFFAOYSA-N |
M.W : | 226.27 | Pubchem ID : | 545317 |
Synonyms : |
|
Signal Word: | Danger | Class: | 8 |
Precautionary Statements: | P261-P280-P305+P351+P338-P310 | UN#: | 3261 |
Hazard Statements: | H314-H335 | Packing Group: | Ⅲ |
GHS Pictogram: |
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* 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 |
---|---|---|
75% | With triphenylphosphine In dichloromethane for 24h; Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
36% | With triphenylphosphine In dichloromethane at -10 - 20℃; for 6h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With triphenylphosphine In dichloromethane at 20℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | In dichloromethane at 38℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | In dichloromethane at 38℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | In ethyl acetate at 20℃; for 6h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | In acetone at -10℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | In acetone at -10℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
58% | Stage #1: 2-methylthio-1,3-thiazole; Trimethylsilylmethyl trifluoromethanesulfonate In acetonitrile at 20℃; for 0.5h; Stage #2: Di-tert-butyl acetylenedicarboxylate With cesium fluoride In acetonitrile at 20℃; for 2h; Further stages.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
21% | With hydrogen In dichloromethane at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | In ethyl acetate at -5 - 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | In diethyl ether at -5 - 20℃; for 10h; chemoselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | In ethyl acetate for 24h; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | In dichloromethane at 20℃; for 48h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | In dichloromethane at 20℃; for 8h; | Typical procedure for the preparation of dimethyl 2-((2,4,4-trimethylpentan-2-ylimino)methylene)-3-(triphenylsilyloxy)succinate (4a): General procedure: To a magnetically stirred solution of triphenylsilanol (0.28 g, 1.0 mmol) and dimethyl acetylenedicarboxylate (0.14 g, 1.0 mmol) in 10 mL CH2Cl2 was added, 1,1,3,3-tetramethyl-butyl isocyanide (0.14 g, 1.0 mmol). The mixture was finally stirred for 8 h at room temperature. The solvent was removed under vacuum and the products were thus obtained as yellow oil, yield 0.51 g (92%); |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | In dichloromethane at 20℃; for 8h; | Typical procedure for the preparation of dimethyl 2-((2,4,4-trimethylpentan-2-ylimino)methylene)-3-(triphenylsilyloxy)succinate (4a): General procedure: To a magnetically stirred solution of triphenylsilanol (0.28 g, 1.0 mmol) and dimethyl acetylenedicarboxylate (0.14 g, 1.0 mmol) in 10 mL CH2Cl2 was added, 1,1,3,3-tetramethyl-butyl isocyanide (0.14 g, 1.0 mmol). The mixture was finally stirred for 8 h at room temperature. The solvent was removed under vacuum and the products were thus obtained as yellow oil, yield 0.51 g (92%); |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | In dichloromethane at 20℃; for 8h; | Typical procedure for the preparation of dimethyl 2-((2,4,4-trimethylpentan-2-ylimino)methylene)-3-(triphenylsilyloxy)succinate (4a): General procedure: To a magnetically stirred solution of triphenylsilanol (0.28 g, 1.0 mmol) and dimethyl acetylenedicarboxylate (0.14 g, 1.0 mmol) in 10 mL CH2Cl2 was added, 1,1,3,3-tetramethyl-butyl isocyanide (0.14 g, 1.0 mmol). The mixture was finally stirred for 8 h at room temperature. The solvent was removed under vacuum and the products were thus obtained as yellow oil, yield 0.51 g (92%); |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | In 1,4-dioxane at 25℃; for 12h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With pyridine; In dichloromethane; at 20℃; for 2h; | General procedure: A mixture of pyridine (1 mmol) in 3 mL dichloromethane was added dropwise to a magnetically stirred solution of 2-mercapto-1-methylimidazole or 5-mercapto-1-methyltetrazole (1 mmol) and acetylenic esters (1 mmol) in 15 mL dichloromethane. The reaction mixture was then stirred for 2 h at room temperature. The solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography using hexane-ethyl acetate as eluent. The solvent was removed under reduced pressure to afford the product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With pyridine; In dichloromethane; at 20℃; for 2h; | General procedure: A mixture of pyridine (1 mmol) in 3 mL dichloromethane was added dropwise to a magnetically stirred solution of 2-mercapto-1-methylimidazole or <strong>[13183-79-4]5-mercapto-1-methyltetrazole</strong> (1 mmol) and acetylenic esters (1 mmol) in 15 mL dichloromethane. The reaction mixture was then stirred for 2 h at room temperature. The solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography using hexane-ethyl acetate as eluent. The solvent was removed under reduced pressure to afford the product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
30% | With triethylamine; In tetrahydrofuran; at 20℃; | General procedure: To a magnetically-stirred solution of 7-hydroxycoumarin derivatives (2 mmol), aromatic aldehydes (2 mmol) and NEt3 (2 mmol) in THF (8 mL) a mixture of dialkyl acetylenedicarboxylate (2 mmol) in THF (2 mL) was added in 15 min. The reaction mixture was then allowed to stand at room temperature for 0.5-10 h. After completion of the reaction as indicated by thin-layer chromatography (TLC) (n-hexane/EtOAc, 1:1), the solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel (Merck, 230-400 mesh) using a mixture of n-hexane/EtOAc (1:1) as eluent to afford the pure product as a light yellow powder. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | In dichloromethane; at 20℃; for 5.25h; | General procedure: To a stirred mixture of N,N-methylenediacrilamide (0.154 g, 1 mmol) and dialkylacetylenedicarboxylate (1 mmol) in CH2Cl2 (5 mL) was added, drop wise, a mixture oftrialkyl(aryl) phosphite (1 mmol) in CH2Cl2 (3 mL) at room temperature over 15 min.After completion of the reaction (about 5 h), as indicated by TLC (EtOAc/hexane, 3:2), thesolvent was removed under reduced pressure, the solid residue was washed with cold Et2O(2 × 5 mL), to afford the pure adducts. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | In dichloromethane; at 20℃; for 5.25h; | General procedure: To a stirred mixture of N,N-methylenediacrilamide (0.154 g, 1 mmol) and dialkylacetylenedicarboxylate (1 mmol) in CH2Cl2 (5 mL) was added, drop wise, a mixture oftrialkyl(aryl) phosphite (1 mmol) in CH2Cl2 (3 mL) at room temperature over 15 min.After completion of the reaction (about 5 h), as indicated by TLC (EtOAc/hexane, 3:2), thesolvent was removed under reduced pressure, the solid residue was washed with cold Et2O(2 × 5 mL), to afford the pure adducts. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | In dichloromethane; at 20℃; for 5.25h; | General procedure: To a stirred mixture of N,N-methylenediacrilamide (0.154 g, 1 mmol) and dialkylacetylenedicarboxylate (1 mmol) in CH2Cl2 (5 mL) was added, drop wise, a mixture oftrialkyl(aryl) phosphite (1 mmol) in CH2Cl2 (3 mL) at room temperature over 15 min.After completion of the reaction (about 5 h), as indicated by TLC (EtOAc/hexane, 3:2), thesolvent was removed under reduced pressure, the solid residue was washed with cold Et2O(2 × 5 mL), to afford the pure adducts. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | With triethylamine In ethanol at 20℃; for 10h; | General procedure for the preparation of compounds 5a-d General procedure: To a mixture of 2-(3,4-dihydronaphthalen-1(2H)-ylidene)malononitrile 4 (2mmol) and dialkyl acetylenedicarboxylate 2 (1mmol) in EtOH (5mL) was added triethylamine (6 drops). The mixture was stirred at room temperature. After completion, monitored by TLC, the mixture was filtered and the precipitate washed with ethanol (2×4mL) to afford the pure product 5a-d. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | Stage #1: isoquinoline; 3-bromoacetylcoumarin In acetonitrile at 20℃; for 1h; Stage #2: Di-tert-butyl acetylenedicarboxylate With triethylamine In acetonitrile for 4h; | General procedure (exemplified for 3a) General procedure: A solution of isoquinoline (1 mmol, 129 mg) and 3-(2-bromoacetyl)coumarin (1a) (1 mmol, 266 mg) in acetonitrile (5 ml) were magnetically stirred for 1 h at r.t. Then, triethylamine (1 mmol, 101 mg) was added to the mixture and orange participate was formed. Then, dialkyl acetylenedicarboxylate (1 mmol, 142 mg) was added dropwise to the mixture during 5 min and the solution stirred for 4 h. After completion of the reaction [about 5 h; TLC (AcOEt/hexane 1:3)], the mixture was filtered and the precipitate was washed with EtOH (4 ml) to afford the pure product 3a-i (Table 1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In dichloromethane; at -10 - 20℃; | General procedure: To a magnetically stirred solution of methyl 4-oxotetrahydro-2H-thiopyran-3-carboxylate (0.35 g, 2 mmol) and triphenylphosphine (0.52 g, 2 mmol) in CH2Cl2 (10 mL) at-10 C was added drop wise a solution of dialkyl acetylenedicarboxylate (2 mmol) in CH2Cl2 (3 mL) over 10 min. The mixture was allowed to stand at room temperature for 20-30 min. The solvent was removed under reduced pressure andthe residue was precipitated in diethyl ether then filtered andd ried. The products 3a-cwere obtained aswhite powders. Compounds 3a-c were refluxed in toluene for 2 h. After completionof the reaction as indicated by thin layer chromatography (TLC; n-hexane/EtOAc, 3:1), the solvent was removed underreduced pressure and viscous residue was purified by silica gel (Merck silica gel, 230-400 mesh) column chromatography usingn-hexane/ethyl acetate (7:3). The solvent was removed under reduced pressure and products 5a-c were obtained as yellowoils. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
66% | In dimethyl sulfoxide at 80℃; for 12h; Schlenk technique; | |
66% | In dimethyl sulfoxide at 120℃; for 24h; | 46 Example 46 tert-Butyl 3- (3- (tert-butoxy) -2-hydroxy-3-oxopropyl) -1H-indole-2-carboxylate Take a reaction tube,Adding 2-vinyl aniline 24 mg,Butynedoate di-tert-butyl ester 250 mg,Dimethyl sulfoxide 1 mL,And the mixture was stirred at 120 ° C for 24 hours.After completion of the reaction, 10 mL of ethyl acetate was added to harden the reaction, washed with 5 mL of brine, the organic phase was separated, the aqueous phase was extracted three times with ethyl acetate,Combine organic phase,Separated by column chromatography to give 3- (3- (tert-butoxy) -2-hydroxy-3-oxopropyl) lH-indole-2-carboxylate 48mg, yield 66%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | In acetonitrile; at 20℃; for 24h; | General procedure: A mixture of <strong>[550-24-3]2,5-dihydroxy-6-undecyl-1,4-benzoquinone</strong> (1 mmol), diethylacetylene dicarboxylate (1 mmol) and isocyanides (1 mmol) was stirred in CH3CN (5 mL) at RT for 24 h. The progress of the reaction was monitored by TLC (20% methanol in chloroform). After completion of the reaction, the separated solid was filtered off and washed with hexane. The crude product was purified by recrystallization from ethanol to give 4. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | In acetonitrile; at 20℃; for 24h; | General procedure: A mixture of <strong>[550-24-3]2,5-dihydroxy-6-undecyl-1,4-benzoquinone</strong> (1 mmol), diethylacetylene dicarboxylate (1 mmol) and isocyanides (1 mmol) was stirred in CH3CN (5 mL) at RT for 24 h. The progress of the reaction was monitored by TLC (20% methanol in chloroform). After completion of the reaction, the separated solid was filtered off and washed with hexane. The crude product was purified by recrystallization from ethanol to give 4. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | In acetonitrile; at 20℃; for 24h; | General procedure: A mixture of <strong>[550-24-3]2,5-dihydroxy-6-undecyl-1,4-benzoquinone</strong> (1 mmol), diethylacetylene dicarboxylate (1 mmol) and isocyanides (1 mmol) was stirred in CH3CN (5 mL) at RT for 24 h. The progress of the reaction was monitored by TLC (20% methanol in chloroform). After completion of the reaction, the separated solid was filtered off and washed with hexane. The crude product was purified by recrystallization from ethanol to give 4. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64.912 % de | With formic acid; triethanolamine; palladium dichloride In N,N-dimethyl-formamide at 50℃; for 24h; Inert atmosphere; Overall yield = 34 %Spectr.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With triphenylphosphine; In dichloromethane; at 20℃; for 10h; | General procedure: Amixture of dimethyl acetylenedicarboxylate (142 mg, 1 mmol) in CH2Cl2 (3 mL) was added drop wise to amagnetically stirred solution of triphenylphosphine (262 mg, 1 mmol) and phenylhydrazine (108 mg, 1 mmol)in CH2Cl2 (10 mL). The reaction mixture was then stirred for 1 min. 4-Chlorophenylglyoxal monohydrate (186mg, 1 mmol) was added, and the reaction mixture was stirred for more 10 hr at room temperature. Thesolvent was evaporated, and the residue was purified by column chromatography on silica gel using ethylacetate-hexane mixture (4:1 ratio) as eluent to give the product (308 mg, 80%) as a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | In dichloromethane; at 20℃; for 6.08333h; | General procedure: A stirred solution of pyridine (1.0 mmol) and <strong>[15119-34-3]2-oxo-2H-chromene-3-carbonitrile</strong> (1.0 mmol) in CH2Cl2 (15 mL) was treated dropwise with a solution of the acetylenic ester (1.0 mmol) in CH2Cl2 (2 mL) over 5min via a syringe. The reaction mixture was then stirred at roomtemperature for about 6 h. On reaction completion, as monitoredby TLC, the solvent was removed under vacuum and the products7a-g, were crystallised from the residue in ethanol to afford thebenzopyrano[3,4-a]quinolizine 7. For products 8a,b, the residue waspurified through plate chromatography (eluent: EtOAc/petroleumether) using 100-200 mesh silica gel to afford the desired product 8. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85.9% | With triphenyl-arsane; In ethanol; at 0 - 20℃; for 240h; | Triphenylarsine (3.17 g, 1 1 mmol) was dissolved in anhydrous EtOH (50 mL) and mixed with <strong>[52267-39-7]benzyl methyl malonate</strong> (4.6 g, 22.09 mmol). After the solution was cooled in an ice-water bath, it was added with di-tert-butyl acetylene dicarboxylate (5 g, 22.09 mmol). The reaction mixture was stirred at 0 C to room temperature for 10 days. EtOH was removed by rotary evaporation, and the residue was purified through silica gel column chromatography (220 g, 0 to 10 % EtOAc and hexane). Yield 9.2 g, 85.9 %. Ion found by LCMS: [M - 2tBu + H]+ = 323. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 46% 2: 20% | In benzene at 80℃; for 47h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
20% | In o-xylene at 140℃; for 10h; | |
15% | In o-xylene at 140℃; for 10h; chemoselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
31% | With bis(1-methyl-1-phenylethyl)peroxide In dimethyl sulfoxide at 20℃; for 24h; Irradiation; | 15 Implementation example 15 0.018g (0.1mmol) N-methylbenzidine-2-amine 1a, 0.045g (0.2mmol) butyne dicarboxylate 2c, 0.054g (0.2mmol) dicumyl peroxide , 2mL DMSO was sequentially added to a 10ml thick-walled pressure-resistant tube, under the irradiation of 24W blue LED, the reaction was magnetically stirred for 24h, and the progress of the reaction was monitored by TLC. After the reaction is over, column chromatography is separated [petroleum ether (6090)/ethyl acetate (15:1)] to obtain 8-phenyl-3,4-dicarboxylate tert-butyl quinoline 3i, a white solid 13mg The yield was 31%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: benzene / 47 h / 80 °C 2: C30H37Cl2N3Ru / benzene / 6 h / 100 °C / 1500.15 Torr / Autoclave |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: o-xylene / 10 h / 140 °C 2: C30H37Cl2N3Ru / benzene / 6 h / 100 °C / 1500.15 Torr / Autoclave |
Tags: 66086-33-7 synthesis path| 66086-33-7 SDS| 66086-33-7 COA| 66086-33-7 purity| 66086-33-7 application| 66086-33-7 NMR| 66086-33-7 COA| 66086-33-7 structure
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Physical hazards | |
Code | Phrase |
H200 | Unstable explosive |
H201 | Explosive; mass explosion hazard |
H202 | Explosive; severe projection hazard |
H203 | Explosive; fire, blast or projection hazard |
H204 | Fire or projection hazard |
H205 | May mass explode in fire |
H220 | Extremely flammable gas |
H221 | Flammable gas |
H222 | Extremely flammable aerosol |
H223 | Flammable aerosol |
H224 | Extremely flammable liquid and vapour |
H225 | Highly flammable liquid and vapour |
H226 | Flammable liquid and vapour |
H227 | Combustible liquid |
H228 | Flammable solid |
H229 | Pressurized container: may burst if heated |
H230 | May react explosively even in the absence of air |
H231 | May react explosively even in the absence of air at elevated pressure and/or temperature |
H240 | Heating may cause an explosion |
H241 | Heating may cause a fire or explosion |
H242 | Heating may cause a fire |
H250 | Catches fire spontaneously if exposed to air |
H251 | Self-heating; may catch fire |
H252 | Self-heating in large quantities; may catch fire |
H260 | In contact with water releases flammable gases which may ignite spontaneously |
H261 | In contact with water releases flammable gas |
H270 | May cause or intensify fire; oxidizer |
H271 | May cause fire or explosion; strong oxidizer |
H272 | May intensify fire; oxidizer |
H280 | Contains gas under pressure; may explode if heated |
H281 | Contains refrigerated gas; may cause cryogenic burns or injury |
H290 | May be corrosive to metals |
Health hazards | |
Code | Phrase |
H300 | Fatal if swallowed |
H301 | Toxic if swallowed |
H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
H304 | May be fatal if swallowed and enters airways |
H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
Sorry,this product has been discontinued.
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