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7-(benzyloxy)-2-(4-(benzyloxy)phenyl)-5-hydroxy-6-methoxy-4H-chromen-4-one
hispidulin
Conditions | Yield |
---|---|
With palladium 10% on activated carbon; hydrogen In tetrahydrofuran; ethanol under 760.051 Torr; for 8h; Inert atmosphere; | 96% |
With palladium 10% on activated carbon; hydrogen In tetrahydrofuran; ethanol under 760.051 Torr; for 8h; | 96% |
With palladium 10% on activated carbon; hydrogen In tetrahydrofuran; ethanol for 8h; | 96.1% |
With palladium 10% on activated carbon; hydrogen In tetrahydrofuran; ethanol at 20℃; for 8h; | 96% |
hispidulin
Conditions | Yield |
---|---|
With hydrogenchloride In diethyl ether; dichloromethane at 0 - 25℃; for 1h; | 92% |
With hydrogenchloride In diethyl ether; dichloromethane; water at 0 - 25℃; for 1h; |
hispidulin
Conditions | Yield |
---|---|
With sulfuric acid In ethanol; water at 20 - 100℃; Solvent; Temperature; Reagent/catalyst; | 91% |
With sulfuric acid In ethanol; water at 100℃; Inert atmosphere; | 90% |
hispidulin
Conditions | Yield |
---|---|
With boron trichloride In dichloromethane at -78℃; for 1.33333h; | 85% |
With boron trichloride In dichloromethane at -78℃; for 1.33333h; | 85% |
hispidulin
Conditions | Yield |
---|---|
With boron trichloride In dichloromethane at -78 - 20℃; for 1h; Inert atmosphere; | 80% |
Conditions | Yield |
---|---|
With hydrolysis |
hispidulin
Conditions | Yield |
---|---|
With sulfuric acid for 8h; | 95 mg |
hispidulin
Conditions | Yield |
---|---|
With boron trichloride In dichloromethane at -65℃; for 1.5h; |
Conditions | Yield |
---|---|
Multi-step reaction with 8 steps 1: 60 percent / aluminium chloride / chlorobenzene / 1 h / Heating 2: 99 percent / K2CO3 / acetone / Heating 3: 29 percent / NaOH; K2S2O8; pyridine / H2O / 24 h / 20 °C 4: 59 percent / K2CO3 / acetone / Heating 5: pyridine / 3 h / 20 °C 6: KOH / pyridine / 4 h / 60 °C 7: sulfuric acid / acetic acid / 1.5 h / 60 °C 8: BCl3 / CH2Cl2 / 1.5 h / -65 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: pyridine / 3 h / 20 °C 2: KOH / pyridine / 4 h / 60 °C 3: sulfuric acid / acetic acid / 1.5 h / 60 °C 4: BCl3 / CH2Cl2 / 1.5 h / -65 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 9 steps 1: 92 percent / K2CO3 / acetone / 3 h / 65 °C 2: 60 percent / aluminium chloride / chlorobenzene / 1 h / Heating 3: 99 percent / K2CO3 / acetone / Heating 4: 29 percent / NaOH; K2S2O8; pyridine / H2O / 24 h / 20 °C 5: 59 percent / K2CO3 / acetone / Heating 6: pyridine / 3 h / 20 °C 7: KOH / pyridine / 4 h / 60 °C 8: sulfuric acid / acetic acid / 1.5 h / 60 °C 9: BCl3 / CH2Cl2 / 1.5 h / -65 °C View Scheme | |
Multi-step reaction with 9 steps 1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0 °C 2: silver trifluoroacetate; iodine / dichloromethane / 0 °C 3: potassium carbonate / N,N-dimethyl-formamide / 0 °C 4: potassium hydroxide; tris-(dibenzylideneacetone)dipalladium(0); tert-butyl XPhos / water; 1,4-dioxane / 90 °C 5: potassium carbonate / acetone / 5 h / 56 °C 6: potassium hydroxide / water; ethanol / 24.5 h / 0 - 20 °C 7: hydrogenchloride / methanol; tetrahydrofuran / 8 h / 0 - 20 °C 8: iodine / dimethyl sulfoxide / 2 h / 120 °C 9: boron trichloride / dichloromethane / 1.33 h / -78 °C View Scheme |
1-(4-(benzyloxy)-6-hydroxy-2,3-dimethoxyphenyl)ethan-1-one
hispidulin
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: pyridine / 3 h / 20 °C 2: KOH / pyridine / 4 h / 60 °C 3: sulfuric acid / acetic acid / 1.5 h / 60 °C 4: BCl3 / CH2Cl2 / 1.5 h / -65 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1: 99 percent / K2CO3 / acetone / Heating 2: 29 percent / NaOH; K2S2O8; pyridine / H2O / 24 h / 20 °C 3: 59 percent / K2CO3 / acetone / Heating 4: pyridine / 3 h / 20 °C 5: KOH / pyridine / 4 h / 60 °C 6: sulfuric acid / acetic acid / 1.5 h / 60 °C 7: BCl3 / CH2Cl2 / 1.5 h / -65 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: oxalyl chloride / CH2Cl2 / 8 h / 20 °C 2: pyridine / 3 h / 20 °C 3: KOH / pyridine / 4 h / 60 °C 4: sulfuric acid / acetic acid / 1.5 h / 60 °C 5: BCl3 / CH2Cl2 / 1.5 h / -65 °C View Scheme |
1-(4-(benzyloxy)-3,6-dihydroxy-2-methoxyphenyl)ethan-1-one
hispidulin
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: 59 percent / K2CO3 / acetone / Heating 2: pyridine / 3 h / 20 °C 3: KOH / pyridine / 4 h / 60 °C 4: sulfuric acid / acetic acid / 1.5 h / 60 °C 5: BCl3 / CH2Cl2 / 1.5 h / -65 °C View Scheme |
1-(4-(benzyloxy)-2-hydroxy-6-methoxyphenyl)ethan-1-one
hispidulin
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: 29 percent / NaOH; K2S2O8; pyridine / H2O / 24 h / 20 °C 2: 59 percent / K2CO3 / acetone / Heating 3: pyridine / 3 h / 20 °C 4: KOH / pyridine / 4 h / 60 °C 5: sulfuric acid / acetic acid / 1.5 h / 60 °C 6: BCl3 / CH2Cl2 / 1.5 h / -65 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: KOH / H2O; ethanol / 6 h / Heating 2: oxalyl chloride / CH2Cl2 / 8 h / 20 °C 3: pyridine / 3 h / 20 °C 4: KOH / pyridine / 4 h / 60 °C 5: sulfuric acid / acetic acid / 1.5 h / 60 °C 6: BCl3 / CH2Cl2 / 1.5 h / -65 °C View Scheme |
hispidulin
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: KOH / pyridine / 4 h / 60 °C 2: sulfuric acid / acetic acid / 1.5 h / 60 °C 3: BCl3 / CH2Cl2 / 1.5 h / -65 °C View Scheme |
hispidulin
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: sulfuric acid / acetic acid / 1.5 h / 60 °C 2: BCl3 / CH2Cl2 / 1.5 h / -65 °C View Scheme |
scutellarin
hispidulin
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1: hydrogenchloride / ethanol; water / 36 h / Inert atmosphere; Reflux 2: diphenylether / 0.5 h / 175 °C / Inert atmosphere 3: potassium carbonate / N,N-dimethyl-formamide / 14 h / 0 - 25 °C 4: acetic acid / water / 1.5 h / Inert atmosphere; Reflux 5: potassium carbonate / N,N-dimethyl-formamide / 12 h / 0 - 25 °C / Inert atmosphere 6: potassium carbonate / N,N-dimethyl-formamide / 25 °C / Inert atmosphere 7: hydrogen; palladium 10% on activated carbon / ethanol; tetrahydrofuran / 8 h / 760.05 Torr / Inert atmosphere View Scheme | |
Multi-step reaction with 7 steps 1: hydrogenchloride / water; ethanol / 36 h / Inert atmosphere; Reflux 2: diphenylether / 0.5 h / 175 °C / Inert atmosphere 3: potassium carbonate / N,N-dimethyl-formamide / 0 - 25 °C / Inert atmosphere 4: acetic acid / water / 1.5 h / Inert atmosphere; Reflux 5: potassium carbonate / N,N-dimethyl-formamide / 0 - 25 °C / Inert atmosphere 6: potassium carbonate / N,N-dimethyl-formamide / 12 h / 25 °C / Inert atmosphere 7: hydrogen; palladium 10% on activated carbon / ethanol; tetrahydrofuran / 8 h / 760.05 Torr View Scheme | |
Multi-step reaction with 4 steps 1: hydrogenchloride / water; ethanol / 36 h / Inert atmosphere; Reflux 2: potassium carbonate / acetone / 6 h / Reflux 3: potassium carbonate / N,N-dimethyl-formamide / 12 h / 20 °C 4: palladium 10% on activated carbon; hydrogen / ethanol; tetrahydrofuran / 8 h View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: diphenylether / 0.5 h / 175 °C / Inert atmosphere 2: potassium carbonate / N,N-dimethyl-formamide / 14 h / 0 - 25 °C 3: acetic acid / water / 1.5 h / Inert atmosphere; Reflux 4: potassium carbonate / N,N-dimethyl-formamide / 12 h / 0 - 25 °C / Inert atmosphere 5: potassium carbonate / N,N-dimethyl-formamide / 25 °C / Inert atmosphere 6: hydrogen; palladium 10% on activated carbon / ethanol; tetrahydrofuran / 8 h / 760.05 Torr / Inert atmosphere View Scheme | |
Multi-step reaction with 6 steps 1: diphenylether / 0.5 h / 175 °C / Inert atmosphere 2: potassium carbonate / N,N-dimethyl-formamide / 0 - 25 °C / Inert atmosphere 3: acetic acid / water / 1.5 h / Inert atmosphere; Reflux 4: potassium carbonate / N,N-dimethyl-formamide / 0 - 25 °C / Inert atmosphere 5: potassium carbonate / N,N-dimethyl-formamide / 12 h / 25 °C / Inert atmosphere 6: hydrogen; palladium 10% on activated carbon / ethanol; tetrahydrofuran / 8 h / 760.05 Torr View Scheme | |
Multi-step reaction with 3 steps 1: potassium carbonate / acetone / 6 h / Reflux 2: potassium carbonate / N,N-dimethyl-formamide / 12 h / 20 °C 3: palladium 10% on activated carbon; hydrogen / ethanol; tetrahydrofuran / 8 h View Scheme |
9-hydroxy-6-(4-hydroxyphenyl)-2,2-diphenyl-8H-1,3-dioxolo[4,5-g][1]benzopyran-8-one
hispidulin
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: potassium carbonate / N,N-dimethyl-formamide / 14 h / 0 - 25 °C 2: acetic acid / water / 1.5 h / Inert atmosphere; Reflux 3: potassium carbonate / N,N-dimethyl-formamide / 12 h / 0 - 25 °C / Inert atmosphere 4: potassium carbonate / N,N-dimethyl-formamide / 25 °C / Inert atmosphere 5: hydrogen; palladium 10% on activated carbon / ethanol; tetrahydrofuran / 8 h / 760.05 Torr / Inert atmosphere View Scheme | |
Multi-step reaction with 5 steps 1: potassium carbonate / N,N-dimethyl-formamide / 0 - 25 °C / Inert atmosphere 2: acetic acid / water / 1.5 h / Inert atmosphere; Reflux 3: potassium carbonate / N,N-dimethyl-formamide / 0 - 25 °C / Inert atmosphere 4: potassium carbonate / N,N-dimethyl-formamide / 12 h / 25 °C / Inert atmosphere 5: hydrogen; palladium 10% on activated carbon / ethanol; tetrahydrofuran / 8 h / 760.05 Torr View Scheme |
9-hydroxy-2,2-diphenyl-6-[4-(phenylmethoxy)phenyl]-8H-1,3-dioxolo[4,5-g][1]benzopyran-8-one
hispidulin
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: acetic acid / water / 1.5 h / Inert atmosphere; Reflux 2: potassium carbonate / N,N-dimethyl-formamide / 12 h / 0 - 25 °C / Inert atmosphere 3: potassium carbonate / N,N-dimethyl-formamide / 25 °C / Inert atmosphere 4: hydrogen; palladium 10% on activated carbon / ethanol; tetrahydrofuran / 8 h / 760.05 Torr / Inert atmosphere View Scheme | |
Multi-step reaction with 4 steps 1: acetic acid / water / 1.5 h / Inert atmosphere; Reflux 2: potassium carbonate / N,N-dimethyl-formamide / 0 - 25 °C / Inert atmosphere 3: potassium carbonate / N,N-dimethyl-formamide / 12 h / 25 °C / Inert atmosphere 4: hydrogen; palladium 10% on activated carbon / ethanol; tetrahydrofuran / 8 h / 760.05 Torr View Scheme |
5,6,7-trihydroxy-2-[4-(phenylmethoxy)phenyl]-4H-1-benzopyran-4-one
hispidulin
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: potassium carbonate / N,N-dimethyl-formamide / 12 h / 0 - 25 °C / Inert atmosphere 2: potassium carbonate / N,N-dimethyl-formamide / 25 °C / Inert atmosphere 3: hydrogen; palladium 10% on activated carbon / ethanol; tetrahydrofuran / 8 h / 760.05 Torr / Inert atmosphere View Scheme | |
Multi-step reaction with 3 steps 1: potassium carbonate / N,N-dimethyl-formamide / 0 - 25 °C / Inert atmosphere 2: potassium carbonate / N,N-dimethyl-formamide / 12 h / 25 °C / Inert atmosphere 3: hydrogen; palladium 10% on activated carbon / ethanol; tetrahydrofuran / 8 h / 760.05 Torr View Scheme |
7-(benzyloxy)-2-(4-(benzyloxy)phenyl)-5,6-dihydroxy-4H-chromen-4-one
hispidulin
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 12 h / 25 °C / Inert atmosphere 2: hydrogen; palladium 10% on activated carbon / ethanol; tetrahydrofuran / 8 h / 760.05 Torr View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: boron trifluoride diethyl etherate / 20 °C / Cooling with ice; Inert atmosphere 2.1: potassium carbonate / acetone / 56 °C / Inert atmosphere 2.2: 0 - 20 °C / Inert atmosphere 3.1: sodium acetate / water; ethanol / 78 °C / Inert atmosphere 4.1: pyridine; iodine / 3 h / 90 °C 5.1: boron trichloride / dichloromethane / 1 h / -78 - 20 °C / Inert atmosphere View Scheme |
2,4,6-trihydroxy-3-methoxyacetophenone
hispidulin
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: potassium carbonate / acetone / 56 °C / Inert atmosphere 1.2: 0 - 20 °C / Inert atmosphere 2.1: sodium acetate / water; ethanol / 78 °C / Inert atmosphere 3.1: pyridine; iodine / 3 h / 90 °C 4.1: boron trichloride / dichloromethane / 1 h / -78 - 20 °C / Inert atmosphere View Scheme |
hispidulin
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: sodium acetate / water; ethanol / 78 °C / Inert atmosphere 2: pyridine; iodine / 3 h / 90 °C 3: boron trichloride / dichloromethane / 1 h / -78 - 20 °C / Inert atmosphere View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 9 steps 1.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 20 °C / Cooling with ice 2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane; water / 20 °C 3.1: potassium carbonate / acetone / 56 °C / Inert atmosphere 4.1: hydrogenchloride / water; methanol / 20 °C 5.1: boron trifluoride diethyl etherate / 20 °C / Cooling with ice; Inert atmosphere 6.1: potassium carbonate / acetone / 56 °C / Inert atmosphere 6.2: 0 - 20 °C / Inert atmosphere 7.1: sodium acetate / water; ethanol / 78 °C / Inert atmosphere 8.1: pyridine; iodine / 3 h / 90 °C 9.1: boron trichloride / dichloromethane / 1 h / -78 - 20 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 10 steps 1.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.17 h / 0 °C / Inert atmosphere 1.2: 3 h / 0 - 20 °C / Inert atmosphere 2.1: silver trifluoroacetate; iodine / dichloromethane / 5 h / 0 - 20 °C 3.1: potassium carbonate / N,N-dimethyl-formamide / 3 h / 0 - 20 °C 4.1: bis-triphenylphosphine-palladium(II) chloride / toluene / 12 h / 100 °C 5.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 9 h / 0 - 20 °C 5.2: 1.5 h / 20 °C 6.1: potassium carbonate / acetone / 5 h / 56 °C 7.1: potassium hydroxide / water; ethanol / 24.5 h / 0 - 20 °C 8.1: hydrogenchloride / methanol; tetrahydrofuran / 8 h / 0 - 20 °C 9.1: iodine / dimethyl sulfoxide / 2 h / 120 °C 10.1: boron trichloride / dichloromethane / 1.33 h / -78 °C View Scheme | |
Multi-step reaction with 8 steps 1.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.17 h / Cooling with ice; Inert atmosphere 1.2: 3 h / 20 °C / Inert atmosphere 2.1: silver trifluoroacetate; iodine / dichloromethane / 3 h / 0 - 20 °C 2.2: 3 h / 0 - 20 °C 3.1: bis-triphenylphosphine-palladium(II) chloride / toluene / 12 h / 100 °C 4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 8 h / 0 - 20 °C 5.1: potassium carbonate / acetone / 5 h / 56 °C 6.1: potassium hydroxide / ethanol; water / 24.5 h / 0 - 20 °C 6.2: 8 h / 0 - 20 °C 7.1: iodine / dimethyl sulfoxide / 2 h / 120 °C 8.1: boron trichloride / dichloromethane / 1.33 h / -78 °C View Scheme |
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 25℃; for 6h; Inert atmosphere; | A 38% B 49% |
Conditions | Yield |
---|---|
With pyridine hydrochloride for 3h; |
hispidulin
acetic anhydride
5,7,4'-trihydroxy-6-methoxyflavone triacetate
Conditions | Yield |
---|---|
With pyridine |
Conditions | Yield |
---|---|
With pyridine Acetylation; |
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