Hubei CuiRan Biotechnology Co., Ltd is a leading company in the research, development, manufacture and marketing of High Quality Phytochemicals and Extracts(especially Active Ingredients from Traditional Chinese Medicine,Traditional Chinese Medicine)
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Content: 20%,40%, 90% Chemical name: (1,2,12,12a-tetrahidro-2 -iso-propeny-8, 9-dimethoxy-[1]-benzopyrane-[3,4-b] -furo-[2,3-h]-[1]-benzopyran-6-OH)
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(6aS,12aS,5'R)-rotenone enol acetate
rotenone
Conditions | Yield |
---|---|
With hydrogenchloride In methanol for 2h; Heating; | 83% |
diazomethane
(2R,6aS,12aS)-8-hydroxy-9-methoxy-2-(prop-1-en-2-yl)-1,2,12,12a- tetrahydrochromeno[3,4-b]furo[2,3-h]chromen-6(6aH)-one
rotenone
Conditions | Yield |
---|---|
In diethyl ether | 59% |
2-((2R,6aS,12aS)-8,9-dimethoxy-1,2,6,6a,12,12a-hexahydrochromeno[3,4-b]furo[2,3-h]chromen-2-yl)propan-2-ol
A
rotenone
B
Isorotenone
Conditions | Yield |
---|---|
With Burgess Reagent In toluene for 0.5h; Reflux; | A 50% B 13% |
With Burgess Reagent In toluene for 0.5h; Inert atmosphere; Reflux; | A 50% B 13% |
2-((2R,6aS,12aS)-8,9-dimethoxy-1,2,6,6a,12,12a-hexahydrochromeno[3,4-b]furo[2,3-h]chromen-2-yl)propan-2-ol
rotenone
Conditions | Yield |
---|---|
With pyridine; thionyl chloride at 0℃; for 0.5h; | 40% |
(6aS,12aR,5'R)-(trans)-(+)-rotenone
rotenone
Conditions | Yield |
---|---|
With hydrogenchloride In methanol; chloroform for 2h; |
(6aR,12aS,5'R)-rotenone
rotenone
Conditions | Yield |
---|---|
With hydrogenchloride In methanol; chloroform | |
With hydrogenchloride In methanol; chloroform epimerisation; |
Conditions | Yield |
---|---|
With acetic acid; zinc(II) chloride; zinc In water at 100℃; for 2.5h; | 20 mg |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 31 mg / diisobutyaluminium hydride / toluene; tetrahydrofuran / 1 h / -78 °C 2: aq. HCl / methanol; CHCl3 / 2 h View Scheme | |
Multi-step reaction with 2 steps 1: di-isobutylaluminium hydride 2: hydrogen chloride / methanol; CHCl3 / epimerisation View Scheme |
(6aS,12aS,5′R)-rotenone-6′-norketone
A
rotenone
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 50 percent / conc. H2SO4 / 3 h / Heating 2: 1.) n-BuLi / 1.) THF, 35 deg C, 5 min, 2.) THF, 1 h 3: 83 percent / conc. HCl / methanol / 2 h / Heating View Scheme |
rotenone 6'-norketone enol acetate
A
rotenone
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 1.) n-BuLi / 1.) THF, 35 deg C, 5 min, 2.) THF, 1 h 2: 83 percent / conc. HCl / methanol / 2 h / Heating View Scheme |
rotenone
Conditions | Yield |
---|---|
Multi-step reaction with 13 steps 1.1: sodium hydride / hexane; mineral oil; N,N-dimethyl-formamide / 0 - 20 °C 2.1: N-ethyl-N,N-diisopropylamine; tetra-(n-butyl)ammonium iodide / dichloromethane / 24 h / 20 °C 3.1: N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium / hexane; toluene; diethyl ether; cyclohexane / 1 h / -78 °C 3.2: 1.5 h / -78 - -30 °C 4.1: boron trifluoride diethyl etherate / dichloromethane / 0.25 h / 0 °C 5.1: sodium tetrahydroborate / ethanol / 0.5 h / 20 °C 6.1: pyridinium p-toluenesulfonate / dichloromethane / 4 h / 20 °C 7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C 8.1: bis(1,5-cyclooctadiene)nickel (0); tricyclohexylphosphine; potassium tert-butylate / toluene / 2 h / Reflux 9.1: aluminum (III) chloride; lithium aluminium tetrahydride / dichloromethane; toluene; diethyl ether / 0.33 h / 0 °C 10.1: sodium hydride; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; 15-crown-5 / toluene / 2 h / 80 °C 11.1: palladium 10% on activated carbon; hydrogen / tert-butyl alcohol; water / 15 h / 20 °C 12.1: Dess-Martin periodane / dichloromethane / 0.25 h / 20 °C 12.2: 1.5 h / 50 °C 13.1: pyridine; thionyl chloride / 0.5 h / 0 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 13 steps 1.1: sodium hydride / hexane; mineral oil; N,N-dimethyl-formamide / 0 - 20 °C 2.1: N-ethyl-N,N-diisopropylamine; tetra-(n-butyl)ammonium iodide / dichloromethane / 24 h / 20 °C 3.1: N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium / hexane; toluene; diethyl ether; cyclohexane / 1 h / -78 °C 3.2: 1.5 h / -78 - -30 °C 4.1: boron trifluoride diethyl etherate / dichloromethane / 0.25 h / 0 °C 5.1: sodium tetrahydroborate / ethanol / 0.5 h / 20 °C 6.1: pyridinium p-toluenesulfonate / dichloromethane / 4 h / 20 °C 7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C 8.1: bis(1,5-cyclooctadiene)nickel (0); tricyclohexylphosphine; potassium tert-butylate / toluene / 2 h / Reflux 9.1: aluminum (III) chloride; lithium aluminium tetrahydride / dichloromethane; toluene; diethyl ether / 0.33 h / 0 °C 10.1: sodium hydride; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; 15-crown-5 / toluene / 2 h / 80 °C 11.1: palladium 10% on activated carbon; hydrogen / tert-butyl alcohol; water / 15 h / 20 °C 12.1: Dess-Martin periodane / dichloromethane / 0.25 h / 20 °C 12.2: 1.5 h / 50 °C 13.1: Burgess Reagent / toluene / 0.5 h / Reflux View Scheme |
rotenone
Conditions | Yield |
---|---|
Multi-step reaction with 12 steps 1.1: N-ethyl-N,N-diisopropylamine; tetra-(n-butyl)ammonium iodide / dichloromethane / 24 h / 20 °C 2.1: N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium / hexane; toluene; diethyl ether; cyclohexane / 1 h / -78 °C 2.2: 1.5 h / -78 - -30 °C 3.1: boron trifluoride diethyl etherate / dichloromethane / 0.25 h / 0 °C 4.1: sodium tetrahydroborate / ethanol / 0.5 h / 20 °C 5.1: pyridinium p-toluenesulfonate / dichloromethane / 4 h / 20 °C 6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C 7.1: bis(1,5-cyclooctadiene)nickel (0); tricyclohexylphosphine; potassium tert-butylate / toluene / 2 h / Reflux 8.1: aluminum (III) chloride; lithium aluminium tetrahydride / dichloromethane; toluene; diethyl ether / 0.33 h / 0 °C 9.1: sodium hydride; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; 15-crown-5 / toluene / 2 h / 80 °C 10.1: palladium 10% on activated carbon; hydrogen / tert-butyl alcohol; water / 15 h / 20 °C 11.1: Dess-Martin periodane / dichloromethane / 0.25 h / 20 °C 11.2: 1.5 h / 50 °C 12.1: pyridine; thionyl chloride / 0.5 h / 0 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 12 steps 1.1: N-ethyl-N,N-diisopropylamine; tetra-(n-butyl)ammonium iodide / dichloromethane / 24 h / 20 °C 2.1: N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium / hexane; toluene; diethyl ether; cyclohexane / 1 h / -78 °C 2.2: 1.5 h / -78 - -30 °C 3.1: boron trifluoride diethyl etherate / dichloromethane / 0.25 h / 0 °C 4.1: sodium tetrahydroborate / ethanol / 0.5 h / 20 °C 5.1: pyridinium p-toluenesulfonate / dichloromethane / 4 h / 20 °C 6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C 7.1: bis(1,5-cyclooctadiene)nickel (0); tricyclohexylphosphine; potassium tert-butylate / toluene / 2 h / Reflux 8.1: aluminum (III) chloride; lithium aluminium tetrahydride / dichloromethane; toluene; diethyl ether / 0.33 h / 0 °C 9.1: sodium hydride; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; 15-crown-5 / toluene / 2 h / 80 °C 10.1: palladium 10% on activated carbon; hydrogen / tert-butyl alcohol; water / 15 h / 20 °C 11.1: Dess-Martin periodane / dichloromethane / 0.25 h / 20 °C 11.2: 1.5 h / 50 °C 12.1: Burgess Reagent / toluene / 0.5 h / Reflux View Scheme |
rotenone
Conditions | Yield |
---|---|
Multi-step reaction with 11 steps 1.1: N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium / hexane; toluene; diethyl ether; cyclohexane / 1 h / -78 °C 1.2: 1.5 h / -78 - -30 °C 2.1: boron trifluoride diethyl etherate / dichloromethane / 0.25 h / 0 °C 3.1: sodium tetrahydroborate / ethanol / 0.5 h / 20 °C 4.1: pyridinium p-toluenesulfonate / dichloromethane / 4 h / 20 °C 5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C 6.1: bis(1,5-cyclooctadiene)nickel (0); tricyclohexylphosphine; potassium tert-butylate / toluene / 2 h / Reflux 7.1: aluminum (III) chloride; lithium aluminium tetrahydride / dichloromethane; toluene; diethyl ether / 0.33 h / 0 °C 8.1: sodium hydride; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; 15-crown-5 / toluene / 2 h / 80 °C 9.1: palladium 10% on activated carbon; hydrogen / tert-butyl alcohol; water / 15 h / 20 °C 10.1: Dess-Martin periodane / dichloromethane / 0.25 h / 20 °C 10.2: 1.5 h / 50 °C 11.1: pyridine; thionyl chloride / 0.5 h / 0 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 11 steps 1.1: N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium / hexane; toluene; diethyl ether; cyclohexane / 1 h / -78 °C 1.2: 1.5 h / -78 - -30 °C 2.1: boron trifluoride diethyl etherate / dichloromethane / 0.25 h / 0 °C 3.1: sodium tetrahydroborate / ethanol / 0.5 h / 20 °C 4.1: pyridinium p-toluenesulfonate / dichloromethane / 4 h / 20 °C 5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C 6.1: bis(1,5-cyclooctadiene)nickel (0); tricyclohexylphosphine; potassium tert-butylate / toluene / 2 h / Reflux 7.1: aluminum (III) chloride; lithium aluminium tetrahydride / dichloromethane; toluene; diethyl ether / 0.33 h / 0 °C 8.1: sodium hydride; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; 15-crown-5 / toluene / 2 h / 80 °C 9.1: palladium 10% on activated carbon; hydrogen / tert-butyl alcohol; water / 15 h / 20 °C 10.1: Dess-Martin periodane / dichloromethane / 0.25 h / 20 °C 10.2: 1.5 h / 50 °C 11.1: Burgess Reagent / toluene / 0.5 h / Reflux View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 15 steps 1.1: N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium / tetrahydrofuran; hexane / 1.42 h / -78 °C 1.2: 2 h / 20 °C 2.1: potassium osmate; potassium hexacyanoferrate(III); potassium carbonate; methanesulfonamide; (9S,9"S)-9,9"-[phthalazine-1,4-diylbis-(oxy)]bis[10,11-dihydro-6'-methoxycinchonane] / tert-butyl alcohol; water / 120 h / 0 - 20 °C 3.1: sodium hydride / hexane; mineral oil; N,N-dimethyl-formamide / 0 - 20 °C 4.1: N-ethyl-N,N-diisopropylamine; tetra-(n-butyl)ammonium iodide / dichloromethane / 24 h / 20 °C 5.1: N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium / hexane; toluene; diethyl ether; cyclohexane / 1 h / -78 °C 5.2: 1.5 h / -78 - -30 °C 6.1: boron trifluoride diethyl etherate / dichloromethane / 0.25 h / 0 °C 7.1: sodium tetrahydroborate / ethanol / 0.5 h / 20 °C 8.1: pyridinium p-toluenesulfonate / dichloromethane / 4 h / 20 °C 9.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C 10.1: bis(1,5-cyclooctadiene)nickel (0); tricyclohexylphosphine; potassium tert-butylate / toluene / 2 h / Reflux 11.1: aluminum (III) chloride; lithium aluminium tetrahydride / dichloromethane; toluene; diethyl ether / 0.33 h / 0 °C 12.1: sodium hydride; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; 15-crown-5 / toluene / 2 h / 80 °C 13.1: palladium 10% on activated carbon; hydrogen / tert-butyl alcohol; water / 15 h / 20 °C 14.1: Dess-Martin periodane / dichloromethane / 0.25 h / 20 °C 14.2: 1.5 h / 50 °C 15.1: pyridine; thionyl chloride / 0.5 h / 0 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 15 steps 1.1: N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium / tetrahydrofuran; hexane / 1.42 h / -78 °C 1.2: 2 h / 20 °C 2.1: potassium osmate; potassium hexacyanoferrate(III); potassium carbonate; methanesulfonamide; (9S,9"S)-9,9"-[phthalazine-1,4-diylbis-(oxy)]bis[10,11-dihydro-6'-methoxycinchonane] / tert-butyl alcohol; water / 120 h / 0 - 20 °C 3.1: sodium hydride / hexane; mineral oil; N,N-dimethyl-formamide / 0 - 20 °C 4.1: N-ethyl-N,N-diisopropylamine; tetra-(n-butyl)ammonium iodide / dichloromethane / 24 h / 20 °C 5.1: N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium / hexane; toluene; diethyl ether; cyclohexane / 1 h / -78 °C 5.2: 1.5 h / -78 - -30 °C 6.1: boron trifluoride diethyl etherate / dichloromethane / 0.25 h / 0 °C 7.1: sodium tetrahydroborate / ethanol / 0.5 h / 20 °C 8.1: pyridinium p-toluenesulfonate / dichloromethane / 4 h / 20 °C 9.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C 10.1: bis(1,5-cyclooctadiene)nickel (0); tricyclohexylphosphine; potassium tert-butylate / toluene / 2 h / Reflux 11.1: aluminum (III) chloride; lithium aluminium tetrahydride / dichloromethane; toluene; diethyl ether / 0.33 h / 0 °C 12.1: sodium hydride; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; 15-crown-5 / toluene / 2 h / 80 °C 13.1: palladium 10% on activated carbon; hydrogen / tert-butyl alcohol; water / 15 h / 20 °C 14.1: Dess-Martin periodane / dichloromethane / 0.25 h / 20 °C 14.2: 1.5 h / 50 °C 15.1: Burgess Reagent / toluene / 0.5 h / Reflux View Scheme |
rotenone
Conditions | Yield |
---|---|
Multi-step reaction with 10 steps 1.1: boron trifluoride diethyl etherate / dichloromethane / 0.25 h / 0 °C 2.1: sodium tetrahydroborate / ethanol / 0.5 h / 20 °C 3.1: pyridinium p-toluenesulfonate / dichloromethane / 4 h / 20 °C 4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C 5.1: bis(1,5-cyclooctadiene)nickel (0); tricyclohexylphosphine; potassium tert-butylate / toluene / 2 h / Reflux 6.1: aluminum (III) chloride; lithium aluminium tetrahydride / dichloromethane; toluene; diethyl ether / 0.33 h / 0 °C 7.1: sodium hydride; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; 15-crown-5 / toluene / 2 h / 80 °C 8.1: palladium 10% on activated carbon; hydrogen / tert-butyl alcohol; water / 15 h / 20 °C 9.1: Dess-Martin periodane / dichloromethane / 0.25 h / 20 °C 9.2: 1.5 h / 50 °C 10.1: pyridine; thionyl chloride / 0.5 h / 0 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 10 steps 1.1: boron trifluoride diethyl etherate / dichloromethane / 0.25 h / 0 °C 2.1: sodium tetrahydroborate / ethanol / 0.5 h / 20 °C 3.1: pyridinium p-toluenesulfonate / dichloromethane / 4 h / 20 °C 4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C 5.1: bis(1,5-cyclooctadiene)nickel (0); tricyclohexylphosphine; potassium tert-butylate / toluene / 2 h / Reflux 6.1: aluminum (III) chloride; lithium aluminium tetrahydride / dichloromethane; toluene; diethyl ether / 0.33 h / 0 °C 7.1: sodium hydride; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; 15-crown-5 / toluene / 2 h / 80 °C 8.1: palladium 10% on activated carbon; hydrogen / tert-butyl alcohol; water / 15 h / 20 °C 9.1: Dess-Martin periodane / dichloromethane / 0.25 h / 20 °C 9.2: 1.5 h / 50 °C 10.1: Burgess Reagent / toluene / 0.5 h / Reflux View Scheme | |
Multi-step reaction with 10 steps 1.1: boron trifluoride diethyl etherate / dichloromethane / 0.25 h / 0 °C / Inert atmosphere 1.2: 0.5 h / 20 °C / Inert atmosphere 2.1: pyridinium p-toluenesulfonate / dichloromethane / 3 h / 20 °C / Inert atmosphere 3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere 4.1: potassium tert-butylate; bis(1,5-cyclooctadiene)nickel (0); tricyclohexylphosphine / toluene / 2 h / Inert atmosphere; Reflux 5.1: aluminum (III) chloride; lithium aluminium tetrahydride / diethyl ether; dichloromethane / 0.33 h / 0 °C / Inert atmosphere 6.1: sodium hydride; 15-crown-5; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone / toluene / 2 h / 80 °C / Inert atmosphere 7.1: 10 wt% Pd(OH)2 on carbon; hydrogen / tetrahydrofuran; tert-butyl alcohol; water / 3 h / 20 °C 8.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 20 °C / Inert atmosphere 9.1: hydrogenchloride / methanol / 1.5 h / 50 °C / Inert atmosphere 10.1: Burgess Reagent / toluene / 0.5 h / Inert atmosphere; Reflux View Scheme |
rotenone
Conditions | Yield |
---|---|
Multi-step reaction with 8 steps 1.1: pyridinium p-toluenesulfonate / dichloromethane / 4 h / 20 °C 2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C 3.1: bis(1,5-cyclooctadiene)nickel (0); tricyclohexylphosphine; potassium tert-butylate / toluene / 2 h / Reflux 4.1: aluminum (III) chloride; lithium aluminium tetrahydride / dichloromethane; toluene; diethyl ether / 0.33 h / 0 °C 5.1: sodium hydride; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; 15-crown-5 / toluene / 2 h / 80 °C 6.1: palladium 10% on activated carbon; hydrogen / tert-butyl alcohol; water / 15 h / 20 °C 7.1: Dess-Martin periodane / dichloromethane / 0.25 h / 20 °C 7.2: 1.5 h / 50 °C 8.1: pyridine; thionyl chloride / 0.5 h / 0 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 8 steps 1.1: pyridinium p-toluenesulfonate / dichloromethane / 4 h / 20 °C 2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C 3.1: bis(1,5-cyclooctadiene)nickel (0); tricyclohexylphosphine; potassium tert-butylate / toluene / 2 h / Reflux 4.1: aluminum (III) chloride; lithium aluminium tetrahydride / dichloromethane; toluene; diethyl ether / 0.33 h / 0 °C 5.1: sodium hydride; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; 15-crown-5 / toluene / 2 h / 80 °C 6.1: palladium 10% on activated carbon; hydrogen / tert-butyl alcohol; water / 15 h / 20 °C 7.1: Dess-Martin periodane / dichloromethane / 0.25 h / 20 °C 7.2: 1.5 h / 50 °C 8.1: Burgess Reagent / toluene / 0.5 h / Reflux View Scheme | |
Multi-step reaction with 9 steps 1: pyridinium p-toluenesulfonate / dichloromethane / 3 h / 20 °C / Inert atmosphere 2: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere 3: potassium tert-butylate; bis(1,5-cyclooctadiene)nickel (0); tricyclohexylphosphine / toluene / 2 h / Inert atmosphere; Reflux 4: aluminum (III) chloride; lithium aluminium tetrahydride / diethyl ether; dichloromethane / 0.33 h / 0 °C / Inert atmosphere 5: sodium hydride; 15-crown-5; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone / toluene / 2 h / 80 °C / Inert atmosphere 6: 10 wt% Pd(OH)2 on carbon; hydrogen / tetrahydrofuran; tert-butyl alcohol; water / 3 h / 20 °C 7: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 20 °C / Inert atmosphere 8: hydrogenchloride / methanol / 1.5 h / 50 °C / Inert atmosphere 9: Burgess Reagent / toluene / 0.5 h / Inert atmosphere; Reflux View Scheme |
rotenone
Conditions | Yield |
---|---|
Multi-step reaction with 9 steps 1.1: sodium tetrahydroborate / ethanol / 0.5 h / 20 °C 2.1: pyridinium p-toluenesulfonate / dichloromethane / 4 h / 20 °C 3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C 4.1: bis(1,5-cyclooctadiene)nickel (0); tricyclohexylphosphine; potassium tert-butylate / toluene / 2 h / Reflux 5.1: aluminum (III) chloride; lithium aluminium tetrahydride / dichloromethane; toluene; diethyl ether / 0.33 h / 0 °C 6.1: sodium hydride; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; 15-crown-5 / toluene / 2 h / 80 °C 7.1: palladium 10% on activated carbon; hydrogen / tert-butyl alcohol; water / 15 h / 20 °C 8.1: Dess-Martin periodane / dichloromethane / 0.25 h / 20 °C 8.2: 1.5 h / 50 °C 9.1: pyridine; thionyl chloride / 0.5 h / 0 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 9 steps 1.1: sodium tetrahydroborate / ethanol / 0.5 h / 20 °C 2.1: pyridinium p-toluenesulfonate / dichloromethane / 4 h / 20 °C 3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C 4.1: bis(1,5-cyclooctadiene)nickel (0); tricyclohexylphosphine; potassium tert-butylate / toluene / 2 h / Reflux 5.1: aluminum (III) chloride; lithium aluminium tetrahydride / dichloromethane; toluene; diethyl ether / 0.33 h / 0 °C 6.1: sodium hydride; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; 15-crown-5 / toluene / 2 h / 80 °C 7.1: palladium 10% on activated carbon; hydrogen / tert-butyl alcohol; water / 15 h / 20 °C 8.1: Dess-Martin periodane / dichloromethane / 0.25 h / 20 °C 8.2: 1.5 h / 50 °C 9.1: Burgess Reagent / toluene / 0.5 h / Reflux View Scheme |
rotenone
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C 2.1: bis(1,5-cyclooctadiene)nickel (0); tricyclohexylphosphine; potassium tert-butylate / toluene / 2 h / Reflux 3.1: aluminum (III) chloride; lithium aluminium tetrahydride / dichloromethane; toluene; diethyl ether / 0.33 h / 0 °C 4.1: sodium hydride; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; 15-crown-5 / toluene / 2 h / 80 °C 5.1: palladium 10% on activated carbon; hydrogen / tert-butyl alcohol; water / 15 h / 20 °C 6.1: Dess-Martin periodane / dichloromethane / 0.25 h / 20 °C 6.2: 1.5 h / 50 °C 7.1: pyridine; thionyl chloride / 0.5 h / 0 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C 2.1: bis(1,5-cyclooctadiene)nickel (0); tricyclohexylphosphine; potassium tert-butylate / toluene / 2 h / Reflux 3.1: aluminum (III) chloride; lithium aluminium tetrahydride / dichloromethane; toluene; diethyl ether / 0.33 h / 0 °C 4.1: sodium hydride; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; 15-crown-5 / toluene / 2 h / 80 °C 5.1: palladium 10% on activated carbon; hydrogen / tert-butyl alcohol; water / 15 h / 20 °C 6.1: Dess-Martin periodane / dichloromethane / 0.25 h / 20 °C 6.2: 1.5 h / 50 °C 7.1: Burgess Reagent / toluene / 0.5 h / Reflux View Scheme | |
Multi-step reaction with 8 steps 1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere 2: potassium tert-butylate; bis(1,5-cyclooctadiene)nickel (0); tricyclohexylphosphine / toluene / 2 h / Inert atmosphere; Reflux 3: aluminum (III) chloride; lithium aluminium tetrahydride / diethyl ether; dichloromethane / 0.33 h / 0 °C / Inert atmosphere 4: sodium hydride; 15-crown-5; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone / toluene / 2 h / 80 °C / Inert atmosphere 5: 10 wt% Pd(OH)2 on carbon; hydrogen / tetrahydrofuran; tert-butyl alcohol; water / 3 h / 20 °C 6: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 20 °C / Inert atmosphere 7: hydrogenchloride / methanol / 1.5 h / 50 °C / Inert atmosphere 8: Burgess Reagent / toluene / 0.5 h / Inert atmosphere; Reflux View Scheme |
rotenone
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1.1: bis(1,5-cyclooctadiene)nickel (0); tricyclohexylphosphine; potassium tert-butylate / toluene / 2 h / Reflux 2.1: aluminum (III) chloride; lithium aluminium tetrahydride / dichloromethane; toluene; diethyl ether / 0.33 h / 0 °C 3.1: sodium hydride; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; 15-crown-5 / toluene / 2 h / 80 °C 4.1: palladium 10% on activated carbon; hydrogen / tert-butyl alcohol; water / 15 h / 20 °C 5.1: Dess-Martin periodane / dichloromethane / 0.25 h / 20 °C 5.2: 1.5 h / 50 °C 6.1: pyridine; thionyl chloride / 0.5 h / 0 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1.1: bis(1,5-cyclooctadiene)nickel (0); tricyclohexylphosphine; potassium tert-butylate / toluene / 2 h / Reflux 2.1: aluminum (III) chloride; lithium aluminium tetrahydride / dichloromethane; toluene; diethyl ether / 0.33 h / 0 °C 3.1: sodium hydride; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; 15-crown-5 / toluene / 2 h / 80 °C 4.1: palladium 10% on activated carbon; hydrogen / tert-butyl alcohol; water / 15 h / 20 °C 5.1: Dess-Martin periodane / dichloromethane / 0.25 h / 20 °C 5.2: 1.5 h / 50 °C 6.1: Burgess Reagent / toluene / 0.5 h / Reflux View Scheme | |
Multi-step reaction with 7 steps 1: potassium tert-butylate; bis(1,5-cyclooctadiene)nickel (0); tricyclohexylphosphine / toluene / 2 h / Inert atmosphere; Reflux 2: aluminum (III) chloride; lithium aluminium tetrahydride / diethyl ether; dichloromethane / 0.33 h / 0 °C / Inert atmosphere 3: sodium hydride; 15-crown-5; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone / toluene / 2 h / 80 °C / Inert atmosphere 4: 10 wt% Pd(OH)2 on carbon; hydrogen / tetrahydrofuran; tert-butyl alcohol; water / 3 h / 20 °C 5: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 20 °C / Inert atmosphere 6: hydrogenchloride / methanol / 1.5 h / 50 °C / Inert atmosphere 7: Burgess Reagent / toluene / 0.5 h / Inert atmosphere; Reflux View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 15 steps 1.1: N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium / tetrahydrofuran; hexane / 1.42 h / -78 °C 1.2: 2 h / 20 °C 2.1: potassium osmate; potassium hexacyanoferrate(III); potassium carbonate; methanesulfonamide; (9S,9"S)-9,9"-[phthalazine-1,4-diylbis-(oxy)]bis[10,11-dihydro-6'-methoxycinchonane] / tert-butyl alcohol; water / 120 h / 0 - 20 °C 3.1: sodium hydride / hexane; mineral oil; N,N-dimethyl-formamide / 0 - 20 °C 4.1: N-ethyl-N,N-diisopropylamine; tetra-(n-butyl)ammonium iodide / dichloromethane / 24 h / 20 °C 5.1: N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium / hexane; toluene; diethyl ether; cyclohexane / 1 h / -78 °C 5.2: 1.5 h / -78 - -30 °C 6.1: boron trifluoride diethyl etherate / dichloromethane / 0.25 h / 0 °C 7.1: sodium tetrahydroborate / ethanol / 0.5 h / 20 °C 8.1: pyridinium p-toluenesulfonate / dichloromethane / 4 h / 20 °C 9.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C 10.1: bis(1,5-cyclooctadiene)nickel (0); tricyclohexylphosphine; potassium tert-butylate / toluene / 2 h / Reflux 11.1: aluminum (III) chloride; lithium aluminium tetrahydride / dichloromethane; toluene; diethyl ether / 0.33 h / 0 °C 12.1: sodium hydride; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; 15-crown-5 / toluene / 2 h / 80 °C 13.1: palladium 10% on activated carbon; hydrogen / tert-butyl alcohol; water / 15 h / 20 °C 14.1: Dess-Martin periodane / dichloromethane / 0.25 h / 20 °C 14.2: 1.5 h / 50 °C 15.1: pyridine; thionyl chloride / 0.5 h / 0 °C View Scheme |
rotenone
2R,6aS,12aS-2-isopropyl-8,9-dimethoxy-1,2,12,12a-tetrahydrochromeno[3,4-b]furo[2,3-h]chromen-6(6aH)-one
Conditions | Yield |
---|---|
With palladium 10% on activated carbon; hydrogen In dichloromethane at 20℃; | 98% |
With hydrogen; palladium on activated charcoal In ethyl acetate Ambient temperature; | 94% |
With hydrogen; palladium on activated charcoal In acetone | 90% |
rotenone
Conditions | Yield |
---|---|
With sodium tetrahydroborate In methanol at 50℃; for 2h; | 98% |
With sodium tetrahydroborate In methanol at 0℃; for 3h; | 95% |
Multi-step reaction with 2 steps 1: two-dimensional iron(II) coordination polymer based on a divergent 4'-(4-diphenylamino)phenyl-4,2';6',4''-terpyridine ligand; potassium tert-butylate / tetrahydrofuran / 4 h / 20 °C / Green chemistry 2: silica gel / ethyl acetate; hexane / 20 °C View Scheme | |
With sodium tetrahydroborate In methanol at 0 - 20℃; for 2h; |
Conditions | Yield |
---|---|
With caesium carbonate; Benzene-1,2-dithiol In 1,4-dioxane at 10℃; for 7h; Inert atmosphere; Glovebox; | 96% |
rotenone
(6aS,12S,12aR,5′R)-12-deoxo-12-hydroxyrotenone
Conditions | Yield |
---|---|
With sodium tetrahydroborate In methanol at 20℃; for 2h; Inert atmosphere; | 92% |
With sodium tetrahydroborate In methanol | 85% |
With lithium aluminium tetrahydride Reduction; | |
With lithium aluminium tetrahydride In tetrahydrofuran for 3h; Reduction; Heating; |
Conditions | Yield |
---|---|
With dipotassium hydrogenphosphate; tris(1,10-phenanthroline)ruthenium(II) dichloride In dichloromethane at 25℃; for 15h; Inert atmosphere; Irradiation; regioselective reaction; | 92% |
With dipotassium hydrogenphosphate; tris(1,10-phenanthroline)ruthenium(II) dichloride In dichloromethane at 25℃; for 15h; Photolysis; regioselective reaction; | 92% |
With 2,4,6-trimethyl-pyridine; [Hf6(μ3-O)4(mu3-OH)4(formato)5.9(eosinato Y)0.1(4'-(4-carboxylatophenyl)[2,2':6',2''-terpyridine]-5,5''-dicarboxylato-Fe(OTf)2)2] In acetonitrile at 20℃; for 2h; Catalytic behavior; Inert atmosphere; Schlenk technique; Irradiation; | 70% |
rotenone
(2R,6aR,12aS)-8,9-dimethoxy-2-(prop-1-en-2-yl)-1,2,12,12a-tetrahydrochromeno[3,4-b]furo[2,3-h]chromen-6(6aH)-one oxime
Conditions | Yield |
---|---|
With hydroxylamine hydrochloride; sodium acetate In ethanol for 10h; Reflux; | 91% |
With hydroxylamine hydrochloride; sodium acetate In ethanol for 18h; Reflux; | 74% |
With pyridine; hydroxylamine hydrochloride | 70% |
With hydroxylamine |
rotenone
Conditions | Yield |
---|---|
With sodium acetate; hydrazine hydrate In ethanol at 80℃; for 5h; | 91% |
Conditions | Yield |
---|---|
With Rh2(esp)2 In dichloromethane at 22℃; for 4h; Inert atmosphere; diastereoselective reaction; | 88% |
rotenone
Conditions | Yield |
---|---|
With potassium hydroxide; hydrazine In ethanol Heating; | 87% |
With hydrazine hydrate In ethanol |
rotenone
(6aS,12aS,5’R)-rotenone hydrobromide
Conditions | Yield |
---|---|
With hydrogen bromide; acetic acid at 20℃; for 0.5h; | 87% |
Conditions | Yield |
---|---|
Stage #1: rotenone With copper diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In tetrahydrofuran for 0.0833333h; Inert atmosphere; Stage #2: 1,2-propanediene With (dimethoxy)methylsilane In tetrahydrofuran at 20℃; for 12h; Inert atmosphere; diastereoselective reaction; | 86% |
Conditions | Yield |
---|---|
With potassium hydroxide In ethanol Heating; | 85% |
rotenone
2-((2R,6aS,12aS)-8,9-dimethoxy-1,2,6,6a,12,12a-hexahydrochromeno[3,4-b]furo[2,3-h]chromen-2-yl)propan-2-ol
Conditions | Yield |
---|---|
With iron(III)-acetylacetonate; methyl 4-nitrobenzenesulfonate; phenylsilane; sodium hydrogencarbonate In methanol at 0 - 20℃; for 12h; Schlenk technique; Inert atmosphere; regioselective reaction; | 85% |
Stage #1: rotenone With mercury(II) diacetate In tetrahydrofuran; water at 20℃; for 18h; Stage #2: With sodium tetrahydroborate; sodium hydrogencarbonate In tetrahydrofuran; water | 48% |
With sodium tetrahydroborate; mercury(II) diacetate 1) H2O, THF, 20 deg C, 10 h, 2) 30 s; Yield given. Multistep reaction; | |
Multi-step reaction with 3 steps 1: 1) H2, pyridine / 1) 5percent Pd-BaSO4 2: 0.37 g / m-chloroperbenzoic acid, NaHCO3 / CH2Cl2; H2O / 0.75 h / 19 °C 3: 66 percent / activated Zn-dust / methanol / Ambient temperature View Scheme |
rotenone
6aS,12aS-8,9-dimethoxy-2-(2-methyloxiran-2-yl)-1,2,12,12a-tetrahydrochromeno[3,4-b]furo[2,3-h]chromen-6(6aH)-one
Conditions | Yield |
---|---|
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 20℃; for 2h; | 85% |
Conditions | Yield |
---|---|
With potassium hydroxide In ethanol Heating; | 84% |
rotenone
(6aS,12aS,5′R)-rotenone-6′-norketone
Conditions | Yield |
---|---|
With sodium periodate; osmium(VIII) oxide In tetrahydrofuran; water; tert-butyl alcohol | 82% |
With sodium periodate; osmium(VIII) oxide | 46% |
Conditions | Yield |
---|---|
With potassium dichromate; acetic acid In water at 20 - 60℃; for 18.5h; | 82% |
With dichromate anion; acetic acid | 51% |
rotenone
(2R,6S,6aS,12aS,2'R,6'S,6'aS,12'aS)-2,2'-Diisopropenyl-8,9,8',9'-tetramethoxy-1,2,12,12a,1',2',12',12'a-octahydro-6aH,6'aH-[6,6']bi[chromeno[3,4-b]furo[2,3-h]chromenyl]-6,6'-diol
Conditions | Yield |
---|---|
In acetic acid; acetonitrile electrochemical reduction; | 80% |
In acetic acid; acetonitrile Product distribution; Mechanism; electrochemical reduction; variation of solvent; | 80 % Chromat. |
rotenone
Conditions | Yield |
---|---|
Stage #1: rotenone With dimethylsulfide borane complex In tetrahydrofuran at 0 - 20℃; for 1.5h; Inert atmosphere; Stage #2: With dihydrogen peroxide; sodium hydroxide In tetrahydrofuran; water at 0 - 20℃; for 18h; | 80% |
Stage #1: rotenone With borane In tetrahydrofuran Reduction; hydroboration; Stage #2: With sodium hydroxide; dihydrogen peroxide Oxidation; |
Conditions | Yield |
---|---|
In water; acetonitrile electrochemical reduction; | 75% |
With sodium hydroxide In ethanol Mechanism; Electrochemical reduction; tetrabutylammonium perchlorate, aqueous or aprotic medium; | 70% |
With sodium hydroxide In ethanol controlled potential electrolysis, tetrabutylammonium perchlorate; other solvent DMF; | 70% |
Conditions | Yield |
---|---|
In ethanol Product distribution; Heating; other amines, also with nitrenonone; | 73% |
In ethanol Heating; | 73% |
Conditions | Yield |
---|---|
With potassium hydroxide In ethanol Heating; | 71% |
Conditions | Yield |
---|---|
In tetrahydrofuran 1.) room temperature, 10 min, 2.) 45-55 deg C, 50 min; | 71% |
(Difluoromethyl)triphenylphosphonium bromide
rotenone
Conditions | Yield |
---|---|
With tris[2-phenylpyridinato-C2,N]iridium(III); copper(ll) bromide In N,N-dimethyl-formamide at 20℃; for 10h; Schlenk technique; Inert atmosphere; Irradiation; | 71% |
Conditions | Yield |
---|---|
With potassium hydroxide In ethanol Heating; | 70% |
methyl iodide
rotenone
(6aS,12aR,5'R)-/(6aR,12aS,5'R)-12a-methylrotenone
Conditions | Yield |
---|---|
With sodium hydride In N,N-dimethyl-formamide at 20℃; for 6h; | 66% |
rotenone
Conditions | Yield |
---|---|
With potassium hydroxide; hydroxylamine hydrochloride In ethanol for 3.5h; Heating; | 66% |
Conditions | Yield |
---|---|
Stage #1: dibromodifluoromethane; rotenone With tetrahydrofuran; eosin at 20℃; for 5h; Irradiation; Inert atmosphere; Schlenk technique; Stage #2: With potassium hydrogencarbonate for 5h; Inert atmosphere; Irradiation; Cooling with ice; Schlenk technique; | 65% |
Conditions | Yield |
---|---|
With eosin y In tetrahydrofuran at 20℃; for 10h; Inert atmosphere; | 65% |
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