溴代十一碳烯

反应条件: temp:0.00; pressure:0.00; stir:

反应条件: temp:0.00; pressure:0.00; stir:

反应条件: temp:0.00; pressure:0.00; stir:

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

实验步骤: Synthesized as described above for compound 1. Quantities: K2CO3 (9.08 g, 66 mmol), methyl-4-hydroxy-benzoate (5.00 g, 33 mmol), 11-bromo-1-undecene (7.6 mL, 34 mmol). Yield 10.1 g (quant). 1NMR: δH (CDCl3; 300 MHz): 1.24-1.52 (12 H, m, CH2), 1.80 (2 H, m, O—CH2—CH2), 2.04 (2 H, m, CH2═CH—CH2), 3.87 (3 H, s, OCH3), 4.00 (2 H, t, 3J=6.5 Hz, O—CH2), 4.95 (2 H, m, CH2═CH), 5.82 (1 H, m, CH2═CH), 6.90 (2 H, d, 3J=9.0 Hz, Ar—H), 7.97 (2 H, d, 3J=9.0 Hz, Ar—H). 13C NMR: δC (CDCl3; 75 MHz): 26.4, 29.3, 29.5, 29.7, 29.8, 29.9, 34.2, 52.2, 68.6, 114.45, 114.5, 122.7, 131.9, 139.6, 163.4, 167.3. Synthesized

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

实验步骤: This example illustrates a synthesis of 1-(16,17-Oxidoheptadecyl)-3,7-dimethylxanthine (inventive compound no. 3516). To a suspension of magnesium (3.10 g, 129 mmol) and a crystal of iodine in THF (10 mL) was added 10-undecenyl bromide (6.00 g, 25.8 mmol, available from MTM) in THF (20 mL) over 40 minutes and the reaction stirred for a further 30 minutes after the addition was complete. The solution was added via a canula over 50 minutes to a suspension of copper iodide (0.50 g, 2.58 mmol) and 1-bromo-6-chloro hexane (6.00 mL, 40.0 mmol) in THF (20 mL) and stirred at 25° C. for 16 hours. Sulfuric acid (1.0M, 50 mL) was added, extracted with diethyl ether (2×60 mL) and the organic solvent dried using magnesium sulfate and the solvent subsequently evaporated. The residue was distilled at 0.75 mmHg to yield 1.78 g (25% yield, b.p. 130°-135° C.) 16-heptadecenyl chloride as a colourless liquid. after the addition stirred at 25° C. for 16 hours extracted with diethyl ether (2×60 mL) the organic solvent dried the solvent subsequently evaporated The residue was distilled at 0.75 mmHg

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

实验步骤: This example illustrates a synthesis of 1-(13,14-Oxidotetradecyl)-3,7-dimethylxanthine (inventive compound no. 3503). To a suspension of magnesium (1.86 g, 77.2 mmol) and a crystal of iodine in THF (20 mL) was added 10-undecenyl bromide (6.00 g, 25.8 mmol) in THF (14 mL) over 40 minutes and the reaction stirred for a further 30 minutes after the addition was complete. The solution was added via a canula over 50 minutes to a suspension of copper iodide (0.50 g, 2.58 mmol) and 1-bromo-3-chloropropane (3.84 mL, 38.7 mmol) in THF (20 mL) and stirred at 25° C. for 16 hours. Sulfuric acid (1.0M, 50 mL) was added, extracted with diethyl ether (2×60 mL) and the organic solvent dried using magnesium sulfate and evaporated. The residue was distilled at 0.25 mmHg to obtain 3.06 g (51% yield, b.p. 98°-100° C.)13-tetradecenyl chloride as a colourless liquid. after the addition stirred at 25° C. for 16 hours extracted with diethyl ether (2×60 mL) the organic solvent dried evaporated The residue was distilled at 0.25 mmHg

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

实验步骤: This example illustrates a synthesis of 1-(12,13-Oxidotridecyl)-3,7-dimethylxanthine (inventive compound no. 2562). To a suspension of magnesium (4.12 g, 172 mmol) and a crystal of iodine in tetrahydrofuran (40 mL) was added 10-undecenyl bromide (8.00 g, 34.3 mmol) in tetrahydrofuran (30 mL) over 30 minutes and the reaction stirred for a further 30 minutes after the addition was complete. The solution was added via a canula over 5 minutes to a solution of ethylene oxide (2.65 g, 60.0 mmol) in tetrahydrofuran (30 mL) and stirred at 25° C. for 16 hours. Saturated ammonium chloride (100 mL) and 1M hydrogen chloride (200 mL) were added and extracted with diethyl ether (2×200 mL). The combined organic extracts were dried (magnesium sulfate) and evaporated to give a residue which was distilled at 1.5 mm Hg to afford 12-tridecenyl alcohol as a clear liquid (4.11 g, 61%, b.p. 98°-101° C.). after the addition stirred at 25° C. for 16 hours extracted with diethyl ether (2×200 mL) The combined organic extracts were dried (magnesium sulfate) evaporated to give a residue which was distilled at 1.5 mm Hg

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

实验步骤: This example illustrates a synthesis of 1-(11,12-Oxidododecyl)-3,7-dimethylxanthine (inventive compound no. 2518). To a suspension of magnesium (6.4 g, 265 mmol) and a crystal of iodine in tetrahydrofuran (40 mL) was added 10-undecenyl bromide (12.25 g, 53.0 mmol, available from MTM) in tetrahydrofuran (30 mL) over 30 minutes and the reaction stirred for a further 30 minutes after the addition was complete. The solution was added via a canula over 5 minutes to a suspension of paraformaldehyde (1.80 g, 60.0 mmol) in tetrahydrofuran (40 mL) and stirred at 25° C. for 16 hours. Saturated ammonium chloride (80 mL) is added and extracted with diethyl ether (2×100 mL). The combined organic extracts are dried using magnesium sulfate and evaporated to give a residue which is distilled at 2 mm Hg to yield 6.53 g (67% yield, b.p. 105°-107° C.) of 11-dodecenyl alcohol as a clear liquid. after the addition stirred at 25° C. for 16 hours extracted with diethyl ether (2×100 mL) The combined organic extracts are dried evaporated to give a residue which is distilled at 2 mm Hg

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

实验步骤: This example illustrates a synthesis of 3-(11,10-Oxidoundecyl)-1-methylthymine (inventive compound no. 1932). Sodium hydride (95%) (168 mg, 7 mmol) was added to a solution of 1-methylthymine (700.5 mg, 5 mmol) in dimethylsulfoxide (15 mL). After 20 minutes of stirring, 1-bromundec-10-ene (1.165 g, 5 mmol) was added and stirred for 12 hours at room temperature. The reaction mixture was then poured into a separatory funnel containing 100 mL of water and extracted with dichloromethane (5×75 mL). The organic extracts were combined, washed with water (50 mL) and saturated aqueous salt solution (50 mL), dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The crude product obtained was further purified by flash chromatography over silica gel using a 20% ethyl acetate/hexane eluant to yield 1.22 g (83.7% yield) 3-(10-undecenyl)-1-methylthymine (inventive compound no. 1931). stirred for 12 hours at room temperature The reaction mixture was then poured into a separatory funnel extracted with dichloromethane (5×75 mL) washed with water (50 mL) and saturated aqueous salt solution (50 mL) dried over anhydrous magnesium sulfate concentrated under reduced pressure The crude product obtained was further purified by flash chromatography over silica gel using a 20% ethyl acetate/hexane eluant

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

实验步骤: This example illustrates a synthesis of N-(9,10-Oxidodecyl)piperidine (inventive compound no. 1619). Sodium hydride (95%) (864 mg, 36 mmol) was added to a solution of piperidine (2.554 g, 30 mmol) in dimethyl sulfoxide (75 mL). After 20 minutes of stirring, 1-bromundec-10-ene (6.99 g, 5 mmol) was added and stirred for 12 hours at room temperature. The reaction mixture was then poured into a separatory funnel containing 100 mL of water and extracted with dichlormethane (5×75 mL). The organic extracts were combined, washed with water (50 mL) and brine (50 mL), dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The crude product obtained was further purified by flash chromatography over silica gel using 5% methanol/dichloromethane eluant to yield 3.12 g (44% yield) N-(10-undecenyl)piperidine (inventive compound no. 1615). stirred for 12 hours at room temperature The reaction mixture was then poured into a separatory funnel extracted with dichlormethane (5×75 mL) washed with water (50 mL) and brine (50 mL) dried over anhydrous magnesium sulfate concentrated under reduced pressure The crude product obtained was further purified by flash chromatography over silica gel using 5% methanol/dichloromethane eluant

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

实验步骤: This example illustrates a synthesis of N-(10,11-Oxidoundecyl)-2-piperidone (inventive compound no. 1618). A mixture of potassium hydroxide (1.55 g, 25 mmol, pellets ground in mortar and pestle) and tetrabutylammonium bromide (1.61 g, 5.0 mmol) was stirred in dry tetrahydrofuran (10 mL). A solution of d-valerolactam (2.5 g, 25 mmol) and 1-bromo-10-undecene (Lancaster, 5.9 g, 25 mmol) in tetrahydrofuran (15 mL) was added by syringe pump over 1 hour. After stirring for a further 6 hours. Water (60 mL) and dichloromethane (60 mL) was added to the reaction mixture. The layers were separated and the aqueous layer was extracted with dichloromethane (2×50 mL). The combined organic layers were washed with water (50 mL) and saturated salt solution (50 mL) and then dried with sodium sulfate. The residue was further purified by chromatography using silica and 30% hexane, ethyl acetate to yield 2.88 g (46% yield) of N-(10-Undecenyl)-2-piperidone (inventive compound no. 1616) as a colorless oil. The layers were separated the aqueous layer was extracted with dichloromethane (2×50 mL) The combined organic layers were washed with water (50 mL) and saturated salt solution (50 mL) dried with sodium sulfate The residue was further purified by chromatography

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

实验步骤: This example illustrates a synthesis of N-(11,10-Oxidoundecyl)glutarimide (inventive compound no. 1611). Sodium hydride (95%) (168 mg, 7 mmol) was added to a solution of glutarimide (565.6 mg, 5 mmol) in dimethyl sulfoxide (15 mL). After 20 minutes of stirring, 1-bromundec-10-ene (1.165 g, 5 mmol) was added and stirred for 12 hours at room temperature. The reaction mixture was then poured into a separatory funnel containing 100 mL of water and extracted with dichlormethane (5×75 mL). The organic extracts were combined, washed with water (50 mL) and brine (50 mL), dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The crude product obtained was further purified by flash chromatography over silica gel using 20% ethyl acetate/hexane eluant to yield 0.777 g (58.6% yield) N-(10-Undecenyl)glutarimide (inventive compound no. 1610). stirred for 12 hours at room temperature The reaction mixture was then poured into a separatory funnel extracted with dichlormethane (5×75 mL) washed with water (50 mL) and brine (50 mL) dried over anhydrous magnesium sulfate concentrated under reduced pressure The crude product obtained was further purified by flash chromatography over silica gel using 20% ethyl acetate/hexane eluant