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CAS No. : | 171258-08-5 | MDL No. : | MFCD29761068 |
Formula : | C16H12O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 220.27 | Pubchem ID : | - |
Synonyms : |
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Signal Word: | Class: | ||
Precautionary Statements: | UN#: | ||
Hazard Statements: | Packing Group: |
* 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 |
---|---|---|
95% | With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); water; diisopropylamine at 80℃; for 12h; Inert atmosphere; | |
95% | With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In N,N-dimethyl-formamide at 20 - 80℃; for 2.25h; Inert atmosphere; | Procedure for the synthesis of 2-(4-methylpent-3-en-2-yl)-1-(2-phenylethynyl)benzene (1n): Step 1: To a solution of 2-bromoacetophenone (20 mmol, 3.98 g) in Et3N (60 mL), under nitrogen atmosphere, phenylacetylene (24 mmol, 2.45 g) and PdCl2(PPh3)2 (2 mol%, 280 mg) were added. The reaction was stirred at rt for 15 min, then CuI (1mol%, 40 mg) was added. The reaction mixture was stirred at 80°C until complete consumption of starting material was detected by TLC analysis (2 h). Then, the solvent was evaporated under reduced pressure and the crude purified by flash chromatography over a silica gel column using a 10:1 mixture of hexane and EtOAc as eluent to afford the corresponding o-alkynylacetophenone in 95% yield. |
95% | With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) In triethylamine at 60℃; for 12h; Inert atmosphere; |
91% | With copper(l) iodide; triethylamine at 60℃; for 4h; | |
91% | Stage #1: 2-bromophenyl methyl ketone With bis-triphenylphosphine-palladium(II) chloride; triethylamine In tetrahydrofuran at 20℃; for 0.166667h; Stage #2: phenylacetylene With copper(l) iodide In tetrahydrofuran at 20℃; for 24h; | |
91% | With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diethylamine at 90℃; for 12h; Inert atmosphere; | |
91% | With potassium phosphate; palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In toluene at 120℃; Schlenk technique; Inert atmosphere; | Alkynes 2 and 9; General Procedure 1 (GP 1) General procedure: In an oven-dried Schlenk tube were added bromoarylcarbonyl 1/8 (100.0-204.8 mg, 0.54 mmol), phenylacetylene (110.2 mg, 1.08 mmol), Pd(OAc)2 (4.8 mg, 4 mol%), xantphos (25 mg, 8 mol%), and K3PO4 (458 mg, 2.16 mmol) followed by anhyd toluene (1.0 mL) at r.t. under N2 atmosphere and the reaction mixture was allowed to stir at 120 °C for 2-6 h. Progress of the alkyne 2 and 9 formation was monitored by TLC until the reaction was complete. Then, the mixture was filtered through Celite and washed with CH2Cl2. Evaporation of the solvent under reduced pressure and purification of the crude material by silica gel column chromatography (PE/EtOAc) furnished the alkyne 2 and 9 (72-91%), respectively, as viscous liquid/semi-solid. |
89% | With triethylamine In water at 80℃; for 6h; | |
84% | With triethylamine In N,N-dimethyl-formamide at 80℃; for 20h; | |
82% | With triethylamine at 90℃; for 15h; | |
82% | With potassium carbonate; (1RS,2RS,3SR,4SR)-1,2,3,4-tetrakis((diphenylphosphanyl)methyl)cyclopentane In N,N-dimethyl-formamide at 140℃; for 20h; | |
82% | With copper(l) iodide; trans-bis(triphenylphosphine)palladium dichloride; triethylamine In tetrahydrofuran at 90℃; for 24h; Inert atmosphere; | |
79% | Stage #1: 2-bromophenyl methyl ketone With copper(l) iodide; tri-tert-butyl phosphine; diisopropylamine In 1,4-dioxane Inert atmosphere; Stage #2: phenylacetylene In 1,4-dioxane at 20℃; Inert atmosphere; | |
79% | With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 50℃; for 18h; Glovebox; Inert atmosphere; | |
75% | With copper(l) iodide; bis(triphenylphosphine)palladium(II)-chloride; triethylamine In N,N-dimethyl-formamide for 1h; Heating; | |
70% | Stage #1: 2-bromophenyl methyl ketone; phenylacetylene With bis-triphenylphosphine-palladium(II) chloride; triethylamine at 20℃; for 0.333333h; Inert atmosphere; Schlenk technique; Stage #2: With copper(l) iodide at 80℃; for 6h; Inert atmosphere; Schlenk technique; | |
70% | With potassium hydroxide In N,N-dimethyl-formamide at 135℃; for 4h; Inert atmosphere; | |
66% | Stage #1: 2-bromophenyl methyl ketone; phenylacetylene With trans-dichlorobis(triphenylphosphine)palladium(II); triethylamine at 20℃; for 0.25h; Inert atmosphere; Stage #2: With copper(l) iodide at 80℃; for 2.5h; Inert atmosphere; | |
65% | With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 80℃; for 18h; Sealed tube; Inert atmosphere; | |
45% | With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In tetrahydrofuran at 60℃; | |
With alkylzinc chloride | ||
With copper(l) iodide; triethylamine | ||
With triethylamine In tetrahydrofuran at 70℃; | ||
94 % Chromat. | With triethylamine In toluene at 80℃; for 2h; | |
With bis-triphenylphosphine-palladium(II) chloride; triethylamine | ||
With potassium phosphate; copper(l) iodide In N,N-dimethyl-formamide at 70℃; for 6h; | ||
Stage #1: 2-bromophenyl methyl ketone; phenylacetylene With bis-triphenylphosphine-palladium(II) chloride; triethylamine at 20℃; for 0.0833333h; Inert atmosphere; Stage #2: With copper(l) iodide at 50℃; | ||
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 50℃; Inert atmosphere; Schlenk technique; | ||
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diisopropylamine for 4h; Heating; Microwave irradiation; | ||
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 50℃; Inert atmosphere; | ||
Stage #1: 2-bromophenyl methyl ketone; phenylacetylene With bis-triphenylphosphine-palladium(II) chloride; triethylamine at 20℃; for 0.25h; Stage #2: With copper(l) iodide at 80℃; | ||
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In tetrahydrofuran Schlenk technique; Inert atmosphere; | ||
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 80℃; Inert atmosphere; | ||
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 20 - 60℃; for 16h; Inert atmosphere; | ||
Stage #1: 2-bromophenyl methyl ketone; phenylacetylene With bis-triphenylphosphine-palladium(II) chloride; triethylamine for 0.0833333h; Inert atmosphere; Stage #2: With copper(l) iodide Inert atmosphere; Heating; | ||
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 50℃; for 12h; Inert atmosphere; | General procedure for the synthesis of aromatic alkynols General procedure: Under nitrogen conditions, 2-bromobenzaldehyde(10 mmol), phenylacetylene (12 mmol), Pd(PPh3)2Cl2(0.2 mmol) and CuI (0.1 mmol) were successively introducedinto a 100-mL two-neck flask equipped with Et3N(40 mL). The resulting mixture was stirred at 50 °C for 12 hand monitored with TLC. After completion, the crude mixturewas filtered through celite and Et3Nwas removed undervacuum. The residue was diluted with EtOAc (60 mL) andwashed with water (2 × 50 mL). The organic layer was driedover Na2SO4,which was further purified via column chromatographyon silica gel (the mixture of petroleum ether andEtOAc was used as elute) to give 2-(phenylethynyl)benzaldehyde(1.83 g) in 89% yield. 2-(phenylethynyl)benzaldehyde was dissolved in methanol(30 mL), and the resulting mixture was cooled to 0 °C. NaBH4 (5 mmol) was added in portions, and the solutionwas stirred for additional 20 min. The reaction was quenchedwith saturated ammonium chloride solution (30 mL).Methanol was removed under vacuum, and the residue wasextracted by EtOAc (2 × 30 mL). The combined organic layerwas dried over anhydrous Na2SO4.After the solvent wasremoved under reduced pressure, (2-(phenylethynyl)phenyl)methanol 1a was obtained (1.76 g) in 95% yield, which wasused directly for the next cyclization without purification. | |
Stage #1: 2-bromophenyl methyl ketone With bis-triphenylphosphine-palladium(II) chloride; triethylamine In tetrahydrofuran at 25℃; for 0.166667h; Inert atmosphere; Stage #2: phenylacetylene With copper(l) iodide In tetrahydrofuran at 25℃; for 24h; Inert atmosphere; | ||
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diisopropylamine at 80℃; for 8h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | With tetrakis(triphenylphosphine) palladium(0); copper(l) chloride; In N,N-dimethyl-formamide; at 80℃; for 3h;Inert atmosphere; | General procedure: To a solution of CuCl (50 mg, 0.5 mmol, 50 mol %), tetrakis(triphenylphosphine)palladium (58 mg, 0.05 mmol, 5 mol %), and 4-iodoanisole (2a) (234 mg, 1 mmol) in DMF (5 mL) in a 20 mL of Schlenk tube was added trimethyl(phenylethynyl)silane (1a) (0.39 mL, 2 mmol). The reaction mixture was stirred for 3 h at 80 C, quenched with 1.0 M HCl, and extracted with diethyl ether (20 mL×3). The combined ethereal layer was washed with brine and dried over MgSO4. Filtration and evaporation afforded a dark yellow oil. Column chromatography (silica gel, hexane/diethyl ether=9:1, Rf=0.14) gave the title compound (197 mg, 0.84 mmol, 84% yield) as white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); tetrabutylammomium bromide; triethylamine In N,N-dimethyl-formamide Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium acetate; In dimethyl sulfoxide; at 120℃; | General procedure: Iodobenzene (0.50mmol), phenylacetylene (0.55mmol), NaOAc (1mmol), and dimethyl sulfoxide (DMSO, 8mL) were mixed. Well-dispersed Pd/Fe3O4GO (0.4mol%) in DMSO (2mL) was added to the mixture with vigorous stirring. After the reaction, the catalyst was separated from the solution by centrifugation. The product was extracted three times with dichloromethane (20mL) and dried using MgSO4. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With copper(ll) sulfate pentahydrate; In 1,2-dichloro-ethane; at 100℃; for 14h;Inert atmosphere; | General procedure: A mixture of 2-(phenylethynyl)acetophenone (1a, 110 mg, 0.5 mmol), 4-methyl-aniline (2b, 75 mg, 0.7 mmol), CuSO4·5H2O (7 mg, 0.025 mmol, 5 mol%) and DCE (2.0 mL) was heated at 100 C (oil bath temperature) with stirring in a 25 mL screw-capped thick-walled Pyrex tube under nitrogen atmosphere. When TLC control showed the completion of the reaction (after 14 h), the reaction mixture was quenched with H2O. The mixture was extracted with dichloromethane (DCM) three times, and dried over Na2SO4. The solvent was evaporated and the crude residue was purified by column chromatography on silica gel to afford 3ab as a white solid in 83% yield (128 mg). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
54% | With copper(ll) sulfate pentahydrate; In 1,2-dichloro-ethane; at 100℃; for 14h;Inert atmosphere; | General procedure: A mixture of 2-(phenylethynyl)acetophenone (1a, 110 mg, 0.5 mmol), 4-methyl-aniline (2b, 75 mg, 0.7 mmol), CuSO4·5H2O (7 mg, 0.025 mmol, 5 molpercent) and DCE (2.0 mL) was heated at 100 °C (oil bath temperature) with stirring in a 25 mL screw-capped thick-walled Pyrex tube under nitrogen atmosphere. When TLC control showed the completion of the reaction (after 14 h), the reaction mixture was quenched with H2O. The mixture was extracted with dichloromethane (DCM) three times, and dried over Na2SO4. The solvent was evaporated and the crude residue was purified by column chromatography on silica gel to afford 3ab as a white solid in 83percent yield (128 mg). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With copper(ll) sulfate pentahydrate In 1,2-dichloro-ethane at 100℃; for 14h; Inert atmosphere; | 4.2 A typical experimental procedure for the synthesis of 1-aminonaphthalene 3ab General procedure: A mixture of 2-(phenylethynyl)acetophenone (1a, 110 mg, 0.5 mmol), 4-methyl-aniline (2b, 75 mg, 0.7 mmol), CuSO4·5H2O (7 mg, 0.025 mmol, 5 mol%) and DCE (2.0 mL) was heated at 100 °C (oil bath temperature) with stirring in a 25 mL screw-capped thick-walled Pyrex tube under nitrogen atmosphere. When TLC control showed the completion of the reaction (after 14 h), the reaction mixture was quenched with H2O. The mixture was extracted with dichloromethane (DCM) three times, and dried over Na2SO4. The solvent was evaporated and the crude residue was purified by column chromatography on silica gel to afford 3ab as a white solid in 83% yield (128 mg). |
79% | With 0.92 mmol/g Cu complex immobilized on 2-formylbenzenesulfonic acid-grafted sodium lignosulfate In 1,2-dichloro-ethane at 100℃; for 12h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | Stage #1: N-(4-hydroxyphenyl)benzenesulfonamide With [bis(acetoxy)iodo]benzene In toluene at 20℃; for 5h; Schlenk technique; Stage #2: 2-(phenylethynyl)acetophenone With silver trifluoroacetate In toluene at 0 - 20℃; for 7.5h; Schlenk technique; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | Stage #1: N-(4-hydroxyphenyl)-4-methylbenzenesulfonamide With [bis(acetoxy)iodo]benzene In toluene at 20℃; for 5h; Schlenk technique; Stage #2: 2-(phenylethynyl)acetophenone With silver trifluoroacetate In toluene at 0 - 20℃; for 7.5h; Schlenk technique; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
34% | Stage #1: pentyltriphenylphosphonium bromide With n-butyllithium In tetrahydrofuran; hexane at 0 - 20℃; for 0.5h; Inert atmosphere; Stage #2: 2-(phenylethynyl)acetophenone In tetrahydrofuran; hexane at 70℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With tetrakis(triphenylphosphine) palladium(0); sodium acetate In toluene at 100℃; for 8h; Inert atmosphere; Schlenk technique; |