7-乙基-10-羟基喜树碱合成路线 (共 84 条)
反应条件
1: 77 percent / conc. H2SO4, 30percent H2O2, FeSO4*7H2O / H2O / 3 h / Ambient temperature 2: 78 percent / 30percent H2O2 / acetic acid / 3.5 h / 70 - 80 °C 3: 49 percent / 1 N H2SO4 / dioxane / 0.5 h / Irradiation View Scheme
参考文献
Chemical and Pharmaceutical Bulletin, , vol. 39, # 6 p. 1446 - 1454
反应条件
1: 1.) OsO4, (DHQD)2-Pyr, 2.) I2, CaCO3 2: 47 percent / ICl 3: 72 percent / aq. HI 4: NaH, LiBr / 1,2-dimethoxy-ethane; dimethylformamide 5: Me3SnSnMe3 / benzene / 70 °C / Irradiation View Scheme
参考文献
Angewandte Chemie, , vol. 107, # 23/24 p. 2948 - 2950
反应条件
1: 47 percent / ICl 2: 72 percent / aq. HI 3: NaH, LiBr / 1,2-dimethoxy-ethane; dimethylformamide 4: Me3SnSnMe3 / benzene / 70 °C / Irradiation View Scheme
参考文献
Angewandte Chemie, , vol. 107, # 23/24 p. 2948 - 2950
反应条件
1.1: boron trifluoride diethyl etherate / dichloromethane / 0.67 h / -78 °C / Inert atmosphere 1.2: -78 °C / Inert atmosphere 2.1: 1,3,5-trimethyl-benzene / 6 h / 160 - 170 °C / Sealed tube; Inert atmosphere 3.1: acetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone / 1,4-dioxane / 0.5 h / 20 °C / Inert atmosphere 3.2: 1 h / 20 °C / Inert atmosphere 4.1: K2OsO4*2H2O; (DHQD)2-PYR; methanesulfonamide; potassium carbonate; potassium hexacyanoferrate(III) / water; tert-butyl alcohol / 48 h / 0 °C / Inert atmosphere 5.1: iodine; calcium carbonate / methanol; water / 15 h / 40 °C / Inert atmosphere 6.1: hydrogen bromide / water / 5 h / 110 °C / Sealed tube; Inert atmosphere View Scheme
参考文献
Chemistry - A European Journal, , vol. 17, # 37 p. 10462 - 10469
反应条件
1.1: 4-(N,N-dimethlyamino)pyridine; triethylamine / dichloromethane / 0.5 h / 20 °C / Inert atmosphere 2.1: boron trifluoride diethyl etherate / dichloromethane / 0.67 h / -78 °C / Inert atmosphere 2.2: -78 °C / Inert atmosphere 3.1: 1,3,5-trimethyl-benzene / 6 h / 160 - 170 °C / Sealed tube; Inert atmosphere 4.1: acetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone / 1,4-dioxane / 0.5 h / 20 °C / Inert atmosphere 4.2: 1 h / 20 °C / Inert atmosphere 5.1: K2OsO4*2H2O; (DHQD)2-PYR; methanesulfonamide; potassium carbonate; potassium hexacyanoferrate(III) / water; tert-butyl alcohol / 48 h / 0 °C / Inert atmosphere 6.1: iodine; calcium carbonate / methanol; water / 15 h / 40 °C / Inert atmosphere 7.1: hydrogen bromide / water / 5 h / 110 °C / Sealed tube; Inert atmosphere View Scheme
参考文献
Chemistry - A European Journal, , vol. 17, # 37 p. 10462 - 10469
反应条件
1: K2OsO4*2H2O; (DHQD)2-PYR; methanesulfonamide; potassium carbonate; potassium hexacyanoferrate(III) / water; tert-butyl alcohol / 48 h / 0 °C / Inert atmosphere 2: iodine; calcium carbonate / methanol; water / 15 h / 40 °C / Inert atmosphere 3: hydrogen bromide / water / 5 h / 110 °C / Sealed tube; Inert atmosphere View Scheme
参考文献
Chemistry - A European Journal, , vol. 17, # 37 p. 10462 - 10469
反应条件
1.1: lithium aluminium tetrahydride / diethyl ether / 0.5 h / 0 °C / Inert atmosphere 2.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 20 °C / Inert atmosphere 3.1: hydroxylamine hydrochloride; sodium hydrogencarbonate / ethanol / 1 h / 20 °C / Inert atmosphere 4.1: hydrogenchloride; Pearlman's catalyst; hydrogen / methanol; water / 12 h / 30 °C / 760.05 Torr 5.1: triethylamine / N,N-dimethyl-formamide / 1 h / 0 °C / Inert atmosphere 6.1: manganese(IV) oxide / dichloromethane / 20 °C / Inert atmosphere 7.1: 4-(N,N-dimethlyamino)pyridine; triethylamine / dichloromethane / 0.5 h / 20 °C / Inert atmosphere 8.1: boron trifluoride diethyl etherate / dichloromethane / 0.67 h / -78 °C / Inert atmosphere 8.2: -78 °C / Inert atmosphere 9.1: 1,3,5-trimethyl-benzene / 6 h / 160 - 170 °C / Sealed tube; Inert atmosphere 10.1: acetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone / 1,4-dioxane / 0.5 h / 20 °C / Inert atmosphere 10.2: 1 h / 20 °C / Inert atmosphere 11.1: K2OsO4*2H2O; (DHQD)2-PYR; methanesulfonamide; potassium carbonate; potassium hexacyanoferrate(III) / water; tert-butyl alcohol / 48 h / 0 °C / Inert atmosphere 12.1: iodine; calcium carbonate / methanol; water / 15 h / 40 °C / Inert atmosphere 13.1: hydrogen bromide / water / 5 h / 110 °C / Sealed tube; Inert atmosphere View Scheme
参考文献
Chemistry - A European Journal, , vol. 17, # 37 p. 10462 - 10469
反应条件
1.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 20 °C / Inert atmosphere 2.1: hydroxylamine hydrochloride; sodium hydrogencarbonate / ethanol / 1 h / 20 °C / Inert atmosphere 3.1: hydrogenchloride; Pearlman's catalyst; hydrogen / methanol; water / 12 h / 30 °C / 760.05 Torr 4.1: triethylamine / N,N-dimethyl-formamide / 1 h / 0 °C / Inert atmosphere 5.1: manganese(IV) oxide / dichloromethane / 20 °C / Inert atmosphere 6.1: 4-(N,N-dimethlyamino)pyridine; triethylamine / dichloromethane / 0.5 h / 20 °C / Inert atmosphere 7.1: boron trifluoride diethyl etherate / dichloromethane / 0.67 h / -78 °C / Inert atmosphere 7.2: -78 °C / Inert atmosphere 8.1: 1,3,5-trimethyl-benzene / 6 h / 160 - 170 °C / Sealed tube; Inert atmosphere 9.1: acetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone / 1,4-dioxane / 0.5 h / 20 °C / Inert atmosphere 9.2: 1 h / 20 °C / Inert atmosphere 10.1: K2OsO4*2H2O; (DHQD)2-PYR; methanesulfonamide; potassium carbonate; potassium hexacyanoferrate(III) / water; tert-butyl alcohol / 48 h / 0 °C / Inert atmosphere 11.1: iodine; calcium carbonate / methanol; water / 15 h / 40 °C / Inert atmosphere 12.1: hydrogen bromide / water / 5 h / 110 °C / Sealed tube; Inert atmosphere View Scheme
参考文献
Chemistry - A European Journal, , vol. 17, # 37 p. 10462 - 10469
反应条件
1.1: hydroxylamine hydrochloride; sodium hydrogencarbonate / ethanol / 1 h / 20 °C / Inert atmosphere 2.1: hydrogenchloride; Pearlman's catalyst; hydrogen / methanol; water / 12 h / 30 °C / 760.05 Torr 3.1: triethylamine / N,N-dimethyl-formamide / 1 h / 0 °C / Inert atmosphere 4.1: manganese(IV) oxide / dichloromethane / 20 °C / Inert atmosphere 5.1: 4-(N,N-dimethlyamino)pyridine; triethylamine / dichloromethane / 0.5 h / 20 °C / Inert atmosphere 6.1: boron trifluoride diethyl etherate / dichloromethane / 0.67 h / -78 °C / Inert atmosphere 6.2: -78 °C / Inert atmosphere 7.1: 1,3,5-trimethyl-benzene / 6 h / 160 - 170 °C / Sealed tube; Inert atmosphere 8.1: acetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone / 1,4-dioxane / 0.5 h / 20 °C / Inert atmosphere 8.2: 1 h / 20 °C / Inert atmosphere 9.1: K2OsO4*2H2O; (DHQD)2-PYR; methanesulfonamide; potassium carbonate; potassium hexacyanoferrate(III) / water; tert-butyl alcohol / 48 h / 0 °C / Inert atmosphere 10.1: iodine; calcium carbonate / methanol; water / 15 h / 40 °C / Inert atmosphere 11.1: hydrogen bromide / water / 5 h / 110 °C / Sealed tube; Inert atmosphere View Scheme
参考文献
Chemistry - A European Journal, , vol. 17, # 37 p. 10462 - 10469
反应条件
1.1: hydrogenchloride; Pearlman's catalyst; hydrogen / methanol; water / 12 h / 30 °C / 760.05 Torr 2.1: triethylamine / N,N-dimethyl-formamide / 1 h / 0 °C / Inert atmosphere 3.1: manganese(IV) oxide / dichloromethane / 20 °C / Inert atmosphere 4.1: 4-(N,N-dimethlyamino)pyridine; triethylamine / dichloromethane / 0.5 h / 20 °C / Inert atmosphere 5.1: boron trifluoride diethyl etherate / dichloromethane / 0.67 h / -78 °C / Inert atmosphere 5.2: -78 °C / Inert atmosphere 6.1: 1,3,5-trimethyl-benzene / 6 h / 160 - 170 °C / Sealed tube; Inert atmosphere 7.1: acetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone / 1,4-dioxane / 0.5 h / 20 °C / Inert atmosphere 7.2: 1 h / 20 °C / Inert atmosphere 8.1: K2OsO4*2H2O; (DHQD)2-PYR; methanesulfonamide; potassium carbonate; potassium hexacyanoferrate(III) / water; tert-butyl alcohol / 48 h / 0 °C / Inert atmosphere 9.1: iodine; calcium carbonate / methanol; water / 15 h / 40 °C / Inert atmosphere 10.1: hydrogen bromide / water / 5 h / 110 °C / Sealed tube; Inert atmosphere View Scheme
参考文献
Chemistry - A European Journal, , vol. 17, # 37 p. 10462 - 10469