3-溴-1-苯基丙-1-酮

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: p-Toluenesulfonic acid in a catalytic amount and ethylene glycol (2.9 g) were added to a solution of 3-bromo-1-phenyl-1-propanone (10 g) in benzene (100 ml), and the mixture was stirred at refluxing temperature for 70 hr. The reaction mixture was washed successively with 10% aqueous potassium carbonate solution and brine, and dried. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography to give 6.0 g of 3,3-ethylenedioxy-3-phenylpropyl bromide. at refluxing temperature for 70 hr The reaction mixture was washed successively with 10% aqueous potassium carbonate solution and brine dried The solvent was evaporated under reduced pressure the obtained residue was purified by silica gel column chromatography

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: p-Toluenesulfonic acid in a catalytic amount and ethylene glycol (2.9 g) were added to a solution of 3-bromo-1-phenyl-1-propanone (10 g) in benzene (100 ml), and the mixture was stirred at refluxing temperature for 70 hr. The reaction mixture was washed successively with 10% aqueous potassium carbonate solution and brine, and dried. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography to give 6.0 g of 3,3-ethylenedioxy-3-phenylpropyl bromide. at refluxing temperature for 70 hr The reaction mixture was washed successively with 10% aqueous potassium carbonate solution and brine dried The solvent was evaporated under reduced pressure the obtained residue was purified by silica gel column chromatography

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: p-Toluenesulfonic acid in a catalytic amount and ethylene glycol (2.9 g) were added to a solution of 3-bromo-1-phenyl-1-propanone (10 g) in benzene (100 ml), and the mixture was stirred at refluxing temperature for 70 hr. The reaction mixture was washed successively with 10% aqueous potassium carbonate solution and brine, and dried. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography to give 6.0 g of 3,3-ethylenedioxy-3-phenylpropyl bromide. at refluxing temperature for 70 hr The reaction mixture was washed successively with 10% aqueous potassium carbonate solution and brine dried The solvent was evaporated under reduced pressure the obtained residue was purified by silica gel column chromatography

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A mixture of 3-bromo-1-phenylpropan-1-one (1.5 g, 8.9 mmol), N-phenacyl piperazine dihydrochloride (2.05 g, 7.4 mmol) and K2CO3 (21.75 mmol) in 30 ml of DMF was treated according to the general preparation 2 to give compound (IV-13), 0.64 g (76%), mp 204-205° C., M+ 336. was treated according to the general preparation 2 to give compound (IV-13), 0.64 g (76%), mp 204-205° C., M+ 336

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: (Du, X.; Guo, C.; Hansell, E.; Doyle, P. S.; Caffrey, C. R.; Holler, T. P.; McKerrow, J. H.; Cohen, F. E. J. Med. Chem. 2002, 45, 2695-2707) Into a round bottom flask containing 3-bromopropiophenone (0.508 g, 2.34 mmol), 20 mL of anhydrous methanol were added and the solution was refluxed for 15 minutes. To the warm ketone solution, thiosemicarbazide (0.184 g, 2.04 mmol) and 1% solution of HOAc (0.2 mL) were added. The reaction mixture was refluxed under nitrogen atmosphere for 17 h, at which point, the solvent was evaporated and, the crude reaction mixture was purified by flash chromatography (30% EtOAc/70% hex) to obtain 0.2498 g (0.873 mmol) of the product in a 37% yield. were added the solution was refluxed for 15 minutes The reaction mixture was refluxed under nitrogen atmosphere for 17 h, at which point the solvent was evaporated the crude reaction mixture was purified by flash chromatography (30% EtOAc/70% hex)

反应条件: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Based on Kulkarni, N. R. Ayyangar, Tetrahedron, 1994, 50, 1243–1260. ]: A mixture of 3-bromopropiophenone (10.65 g, 50 mmol), CuCN (5.82 g, 65 mmol) in DMF (35 mL) was heated under reflux for 6 h. After cooling the mixture to ambient temperature FeCl3 (5 g) in H2O (30 mL)/HCl conc (10 mL) was added and heated to 80° C. for another 20 min. After cooling to room temperature and extraction with ether further purification occurred by destination under reduced pressure (bp.: 140° C., 10 torr). The ketone could be obtained as slightly yellow, low melting (42° C.) solid. was heated under reflux for 6 h was added After cooling to room temperature extraction with ether further purification

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A mixture of 2-naphthalenethiol (12.94 g), 3-bromopropiophenone (17.35 g), cuprous oxide (5.83 g), sodium hydroxide (3.24 g) and dimethylformamide (130 ml) was heated to reflux for 18 hours. The mixture was concentrated and the residue was partitioned between diethyl ether and water. The organic phase was dried (MgSO4) and evaporated. The residue was dissolved in a mixture of ethyl acetate and hexane and treated with charcoal. The solution was filtered and evaporated. The residue was recrystallised from a mixture of methanol and water to give 3-(naphth-2-ylthio)propiophenone (5.23 g, 22%), m.p. 90°-91° C. was heated to reflux for 18 hours The mixture was concentrated the residue was partitioned between diethyl ether and water The organic phase was dried (MgSO4) evaporated The residue was dissolved in a mixture of ethyl acetate and hexane treated with charcoal The solution was filtered evaporated The residue was recrystallised from a mixture of methanol and water

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A mixture of 2-naphthalenethiol (12.94 g), 3-bromopropiophenone (17.35 g), cuprous oxide (5.83 g), sodium hydroxide (3.24 g) and dimethylformamide (130 ml) was heated to reflux for 18 hours. The mixture was concentrated and the residue was partitioned between diethyl ether and water. The organic phase was dried (MgSO4) and evaporated. The residue was dissolved in a mixture of ethyl acetate and hexane and treated with charcoal. The solution was filtered and evaporated. The residue was recrystallised from a mixture of methanol and water to give 3-(naphth-2-ylthio)propiophenone (5.23 g, 22%), m.p. 90°-91° C. was heated to reflux for 18 hours The mixture was concentrated the residue was partitioned between diethyl ether and water The organic phase was dried (MgSO4) evaporated The residue was dissolved in a mixture of ethyl acetate and hexane treated with charcoal The solution was filtered evaporated The residue was recrystallised from a mixture of methanol and water

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Compound 9d was synthesized by a procedure similar to that described for 9a using commercially available 3-bromopropiophenone (8d, 1.0 g, 0.0047 mol), TBDMSOTf (1.4 mL, 5.1 mmol), and Et3N (1.1 mL) in CH2Cl2 (10 mL). After workup, 1.15 g (75%) of crude 9d was isolated as colorless oil with a Z-E ratio of 94:6: 1H NMR (CDCl3) δ 7.64-7.58 (m, 1H), 7.41-7.34 (m, 2H), 7.17 (t, 1H, J=8.04 Hz), 5.25 (q, 1H, J=6.9 Hz), 1.75 (d, 3H, J=6.9 Hz), 1.02 (s, 9H), −0.03 (s, 6H); 13C NMR (CDCl3) δ 148.8, 141.9, 130.2, 129.5, 128.7, 124.1, 122.1, 25.8, 18.3, 11.8, −4.0. C15H23BrOSi. Compound 9d was synthesized by a procedure similar to

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: p-Toluenesulfonic acid in a catalytic amount and ethylene glycol (2.9 g) were added to a solution of 3-bromo-1-phenyl-1-propanone (10 g) in benzene (100 ml), and the mixture was stirred at refluxing temperature for 70 hr. The reaction mixture was washed successively with 10% aqueous potassium carbonate solution and brine, and dried. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography to give 6.0 g of 3,3-ethylenedioxy-3-phenylpropyl bromide. at refluxing temperature for 70 hr The reaction mixture was washed successively with 10% aqueous potassium carbonate solution and brine dried The solvent was evaporated under reduced pressure the obtained residue was purified by silica gel column chromatography