1,3-二辛酰甘油

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: A solution of 2-hydroxy-3-octanoyloxypropyl octanoate (5.0 g.) in ether (30 ml.) was stirred with triethylamine (2.04 ml.) and glutaric anhydride (1.66 g.) for 3.5 hours. Further glutaric anhydride (0.8 g.) was then added together with triethylamine (1.0 ml.). This mixture was heated under reflux until no further starting octanoate could be detected by thin layer chromatography (silica: methylene chloride). The cooled reaction mixture was washed with 1M hydrochloric acid (2×20 ml.), then with water (2×20 ml.), dried (MgSO4) and evaporated to give 2-octanoyloxy-1-(octanoyloxymethyl)ethyl hydrogen glutarate as an oil (6.62 g.); NMR (CDCl3): 0.9 (6H, t, CH3), 1.1-2.1 (22H, m, CH2), 2.4 (8H, m, CH2CO), 4.0-4.4 (4H,m, CH2O), 5.1-5.4 (1H, br.t, CHO), 9.6 (1H, br.s, CO2H)ppm. Mass spectrum (major diagnostic peaks based on M=458, using chemical ionisation techniques): m/e 476 (M+NH4), 360 (M +NH4 --HO2C.(CH2)3.CO2H) This mixture was heated under reflux until The cooled reaction mixture was washed with 1M hydrochloric acid (2×20 ml.) with water (2×20 ml.), dried (MgSO4) evaporated

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

实验步骤: A solution of 2-hydroxy-3-octanoyloxypropyl octanoate (5.0 g.) in ether (30 ml.) was stirred with triethylamine (2.04 ml.) and glutaric anhydride (1.66 g.) for 3.5 hours. Further glutaric anhydride (0.8 g.) was then added together with triethylamine (1.0 ml.). This mixture was heated under reflux until no further starting octanoate could be detected by thin layer chromatography (silica: methylene chloride). The cooled reaction mixture was washed with 1M hydrochloric acid (2×20 ml.), then with water (2×20 ml.), dried (MgSO4) and evaporated to give 2-octanoyloxy-1-(octanoyloxymethyl)ethyl hydrogen glutarate as an oil (6.62 g.); NMR (CDCl3): 0.9 (6H, t, CH3), 1.1-2.1 (22H, m, CH2), 2.4 (8H, m, CH2CO), 4.0-4.4 (4H,m, CH2O), 5.1-5.4 (1H, br.t, CHO), 9.6 (1H, br.s, CO2H)ppm. Mass spectrum (major diagnostic peaks based on M=458, using chemical ionisation techniques): m/e 476 (M+NH4), 360 (M +NH4 --HO2C.(CH2)3.CO2H) This mixture was heated under reflux until The cooled reaction mixture was washed with 1M hydrochloric acid (2×20 ml.) with water (2×20 ml.), dried (MgSO4) evaporated

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

实验步骤: Using a similar procedure to that described in Example 6, but using 5-chloro-2-(2,4-dichlorophenoxy)phenol, adipoyl dichloride and 2-hydroxy-3-octanoyloxypropyl octanoate as starting materials, there was obtained 5-chloro-2-(2,4-dichlorophenoxy)phenyl 2-octanoyloxy-1-(octanoyloxymethyl)ethyl adipate as an oil in 33% yield; NMR (CDCL3): 0.85 (6H, br.s, CH3), 1.25+1.65 (24H, br.s, CH2), 2.3 (8H, m, COCH2), 4.2 (4H, m, OCH2), 5.25 (1H, m, CH), 6.6-7.5 (6H, complex, aromatic H)ppm.

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

实验步骤: Using a similar procedure to that described in Example 6, but using 5-chloro-2-(2,4-dichlorophenoxy)phenol, adipoyl dichloride and 2-hydroxy-3-octanoyloxypropyl octanoate as starting materials, there was obtained 5-chloro-2-(2,4-dichlorophenoxy)phenyl 2-octanoyloxy-1-(octanoyloxymethyl)ethyl adipate as an oil in 33% yield; NMR (CDCL3): 0.85 (6H, br.s, CH3), 1.25+1.65 (24H, br.s, CH2), 2.3 (8H, m, COCH2), 4.2 (4H, m, OCH2), 5.25 (1H, m, CH), 6.6-7.5 (6H, complex, aromatic H)ppm.

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

实验步骤: A solution of 2-hydroxy-3-octanoyloxy-propyl octanoate (7.0 g.) and pyridine (1.5 g.) in chloroform (100 ml.) was treated dropwise at 0°-5° C. with a solution of 5-chloro-2-(2,4-dichlorophenoxy)phenyl 4-chloroformylbutyrate (A) (8.4 g.). The reaction mixture was then stirred at ambient temperature for 1 hour and diluted with ether (300 ml.) and water (200 ml). The organic phase was separated, washed successively with 2M hydrochloric acid (50 ml.), saturated sodium bicarbonate solution (3×50 ml.), and then dried (MgSO4) and evaporated. The residual oil was purified by chromatography on silica gel (50 g.) using a mixture of petrol 60-80 and ether (70:30 v/v) as eluant to give 5-chloro-2-(2,4-dichlorophenoxy)phenyl 2-octanoyloxy-1-(octanoyloxymethyl)ethyl glutarate as an oil.(9.1 g.); NMR (CDCl3): 0.9 (6H, t J=4.0 Hz, CH3), 1.1-7 (20H, complex m, CH2 ), 1.98 (2H,m, CH2), 2.2-2.7 (8H, complex, CO.CH2), 4.0-4.5 (4H,complex, CH2O), 5.25 (1H, br.t J=4.5 Hz, CH), 6.75-7.55 (6H,complex, aromatic H)ppm; mass spectrum (major diagnostic peaks): m/e 585 (16%) [M-0.CO(CH2)6CH3 ], 441. (21%), 385 (12%), 327 (100%), 288 (10%), 201 (10%), 127 (46%). The organic phase was separated washed successively with 2M hydrochloric acid (50 ml.), saturated sodium bicarbonate solution (3×50 ml.) dried (MgSO4) evaporated The residual oil was purified by chromatography on silica gel (50 g.) a mixture of petrol 60-80 and ether (70:30 v/v) as eluant

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

实验步骤: A solution of 2-hydroxy-3-octanoyloxy-propyl octanoate (7.0 g.) and pyridine (1.5 g.) in chloroform (100 ml.) was treated dropwise at 0°-5° C. with a solution of 5-chloro-2-(2,4-dichlorophenoxy)phenyl 4-chloroformylbutyrate (A) (8.4 g.). The reaction mixture was then stirred at ambient temperature for 1 hour and diluted with ether (300 ml.) and water (200 ml). The organic phase was separated, washed successively with 2M hydrochloric acid (50 ml.), saturated sodium bicarbonate solution (3×50 ml.), and then dried (MgSO4) and evaporated. The residual oil was purified by chromatography on silica gel (50 g.) using a mixture of petrol 60-80 and ether (70:30 v/v) as eluant to give 5-chloro-2-(2,4-dichlorophenoxy)phenyl 2-octanoyloxy-1-(octanoyloxymethyl)ethyl glutarate as an oil.(9.1 g.); NMR (CDCl3): 0.9 (6H, t J=4.0 Hz, CH3), 1.1-7 (20H, complex m, CH2 ), 1.98 (2H,m, CH2), 2.2-2.7 (8H, complex, CO.CH2), 4.0-4.5 (4H,complex, CH2O), 5.25 (1H, br.t J=4.5 Hz, CH), 6.75-7.55 (6H,complex, aromatic H)ppm; mass spectrum (major diagnostic peaks): m/e 585 (16%) [M-0.CO(CH2)6CH3 ], 441. (21%), 385 (12%), 327 (100%), 288 (10%), 201 (10%), 127 (46%). The organic phase was separated washed successively with 2M hydrochloric acid (50 ml.), saturated sodium bicarbonate solution (3×50 ml.) dried (MgSO4) evaporated The residual oil was purified by chromatography on silica gel (50 g.) a mixture of petrol 60-80 and ether (70:30 v/v) as eluant

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

实验步骤: A solution of 2-hydroxy-3-octanoyloxypropyl octanoate (5.0 g.) in ether (30 ml.) was stirred with triethylamine (2.04 ml.) and glutaric anhydride (1.66 g.) for 3.5 hours. Further glutaric anhydride (0.8 g.) was then added together with triethylamine (1.0 ml.). This mixture was heated under reflux until no further starting octanoate could be detected by thin layer chromatography (silica: methylene chloride). The cooled reaction mixture was washed with 1M hydrochloric acid (2×20 ml.), then with water (2×20 ml.), dried (MgSO4) and evaporated to give 2-octanoyloxy-1-(octanoyloxymethyl)ethyl hydrogen glutarate as an oil (6.62 g.); NMR (CDCl3): 0.9 (6H, t, CH3), 1.1-2.1 (22H, m, CH2), 2.4 (8H, m, CH2CO), 4.0-4.4 (4H,m, CH2O), 5.1-5.4 (1H, br.t, CHO), 9.6 (1H, br.s, CO2H)ppm. Mass spectrum (major diagnostic peaks based on M=458, using chemical ionisation techniques): m/e 476 (M+NH4), 360 (M +NH4 --HO2C.(CH2)3.CO2H) This mixture was heated under reflux until The cooled reaction mixture was washed with 1M hydrochloric acid (2×20 ml.) with water (2×20 ml.), dried (MgSO4) evaporated

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

实验步骤: Using a similar procedure to that described in Example 6, but using 5-chloro-2-(2,4-dichlorophenoxy)phenol, adipoyl dichloride and 2-hydroxy-3-octanoyloxypropyl octanoate as starting materials, there was obtained 5-chloro-2-(2,4-dichlorophenoxy)phenyl 2-octanoyloxy-1-(octanoyloxymethyl)ethyl adipate as an oil in 33% yield; NMR (CDCL3): 0.85 (6H, br.s, CH3), 1.25+1.65 (24H, br.s, CH2), 2.3 (8H, m, COCH2), 4.2 (4H, m, OCH2), 5.25 (1H, m, CH), 6.6-7.5 (6H, complex, aromatic H)ppm.

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

实验步骤: A solution of 2-hydroxy-3-octanoyloxy-propyl octanoate (7.0 g.) and pyridine (1.5 g.) in chloroform (100 ml.) was treated dropwise at 0°-5° C. with a solution of 5-chloro-2-(2,4-dichlorophenoxy)phenyl 4-chloroformylbutyrate (A) (8.4 g.). The reaction mixture was then stirred at ambient temperature for 1 hour and diluted with ether (300 ml.) and water (200 ml). The organic phase was separated, washed successively with 2M hydrochloric acid (50 ml.), saturated sodium bicarbonate solution (3×50 ml.), and then dried (MgSO4) and evaporated. The residual oil was purified by chromatography on silica gel (50 g.) using a mixture of petrol 60-80 and ether (70:30 v/v) as eluant to give 5-chloro-2-(2,4-dichlorophenoxy)phenyl 2-octanoyloxy-1-(octanoyloxymethyl)ethyl glutarate as an oil.(9.1 g.); NMR (CDCl3): 0.9 (6H, t J=4.0 Hz, CH3), 1.1-7 (20H, complex m, CH2 ), 1.98 (2H,m, CH2), 2.2-2.7 (8H, complex, CO.CH2), 4.0-4.5 (4H,complex, CH2O), 5.25 (1H, br.t J=4.5 Hz, CH), 6.75-7.55 (6H,complex, aromatic H)ppm; mass spectrum (major diagnostic peaks): m/e 585 (16%) [M-0.CO(CH2)6CH3 ], 441. (21%), 385 (12%), 327 (100%), 288 (10%), 201 (10%), 127 (46%). The organic phase was separated washed successively with 2M hydrochloric acid (50 ml.), saturated sodium bicarbonate solution (3×50 ml.) dried (MgSO4) evaporated The residual oil was purified by chromatography on silica gel (50 g.) a mixture of petrol 60-80 and ether (70:30 v/v) as eluant

反应条件: temp:0.00; pressure:0.00; stir: