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CAS No.: | 1343403-10-0 |
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Name: | (3R,3As,3Bs,6As,8As,9Ar)-Octahydro-3-Hydroxy-3,8A-DiMethyl-6-Methylene-1H-Oxireno[8,8A]Azuleno[4,5-B]Furan-5(6H)-One |
Article Data: | 8 |
Molecular Structure: | |
Formula: | C15H20O4 |
Molecular Weight: | 264.321 |
Synonyms: | (3R,3As,3Bs,6As,8As,9Ar)-Octahydro-3-Hydroxy-3,8A-DiMethyl-6-Methylene-1H-Oxireno[8,8A]Azuleno[4,5-B]Furan-5(6H)-One;Epoxymicheliolide |
Density: | 1.28±0.1 g/cm3(Predicted) |
Boiling Point: | 451.6±45.0 °C(Predicted) |
PSA: | 59.06000 |
LogP: | 1.56670 |
(1R,3aR,4aS,6aS,9aS,9bS)-1-hydroxy-1,4a-dimethyl-7-methyleneoctahydro-1H-oxireno[2',3':8,8a]azuleno[4,5-b]furan-8(4aH)-one
Conditions | Yield |
---|---|
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 20℃; for 6h; | 91% |
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 20℃; Solvent; Reagent/catalyst; Temperature; | 85% |
With 3-chloro-benzenecarboperoxoic acid In dichloromethane | 75% |
A
(1R,3aR,4aS,6aS,9aS,9bS)-1-hydroxy-1,4a-dimethyl-7-methyleneoctahydro-1H-oxireno[2',3':8,8a]azuleno[4,5-b]furan-8(4aH)-one
Conditions | Yield |
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With tert.-butylhydroperoxide; selenium(IV) oxide In dichloromethane; water for 3h; | A 14% B 53% C 7% |
parthenolide
(1R,3aR,4aS,6aS,9aS,9bS)-1-hydroxy-1,4a-dimethyl-7-methyleneoctahydro-1H-oxireno[2',3':8,8a]azuleno[4,5-b]furan-8(4aH)-one
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: toluene-4-sulfonic acid / dichloromethane / 23 h / 20 °C / Large scale reaction 2: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 20 °C View Scheme | |
Multi-step reaction with 2 steps 1: toluene-4-sulfonic acid / dichloromethane 2: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 20 °C View Scheme | |
Multi-step reaction with 2 steps 1: toluene-4-sulfonic acid / dichloromethane / 20 °C 2: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 20 °C View Scheme |
(1R,3aR,4aS,6aS,9aS,9bS)-1-hydroxy-1,4a-dimethyl-7-methyleneoctahydro-1H-oxireno[2',3':8,8a]azuleno[4,5-b]furan-8(4aH)-one
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: toluene-4-sulfonic acid / dichloromethane 2: 3-chloro-benzenecarboperoxoic acid / dichloromethane View Scheme |
parthenolide
A
(1R,3aR,4aS,6aS,9aS,9bS)-1-hydroxy-1,4a-dimethyl-7-methyleneoctahydro-1H-oxireno[2',3':8,8a]azuleno[4,5-b]furan-8(4aH)-one
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: toluene-4-sulfonic acid / dichloromethane / 20 °C 2: selenium(IV) oxide; tert.-butylhydroperoxide / water; dichloromethane / 3 h View Scheme |
(1R,3aR,4aS,6aS,9aS,9bS)-1-hydroxy-1,4a-dimethyl-7-methyleneoctahydro-1H-oxireno[2',3':8,8a]azuleno[4,5-b]furan-8(4aH)-one
dimethyl amine
Conditions | Yield |
---|---|
With potassium carbonate In tetrahydrofuran; water at 20℃; | 96% |
(1R,3aR,4aS,6aS,9aS,9bS)-1-hydroxy-1,4a-dimethyl-7-methyleneoctahydro-1H-oxireno[2',3':8,8a]azuleno[4,5-b]furan-8(4aH)-one
d6-dimethylamine hydrochloride
Conditions | Yield |
---|---|
With potassium carbonate In tetrahydrofuran at 20℃; | 90% |
(1R,3aR,4aS,6aS,9aS,9bS)-1-hydroxy-1,4a-dimethyl-7-methyleneoctahydro-1H-oxireno[2',3':8,8a]azuleno[4,5-b]furan-8(4aH)-one
1β,10β-Epoxyguaia-3,11(13)-dien-12,6α-olide
Conditions | Yield |
---|---|
With Martins sulfurane In dichloromethane at 20℃; for 24h; Inert atmosphere; | 67% |
With Martins sulfurane In dichloromethane for 24h; Solvent; Reagent/catalyst; Inert atmosphere; | 65% |
With pyridine; trichlorophosphate at 0℃; for 2h; | 45% |
(1R,3aR,4aS,6aS,9aS,9bS)-1-hydroxy-1,4a-dimethyl-7-methyleneoctahydro-1H-oxireno[2',3':8,8a]azuleno[4,5-b]furan-8(4aH)-one
Conditions | Yield |
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Multi-step reaction with 2 steps 1: pyridine; trichlorophosphate / 2 h / 0 °C 2: potassium carbonate / tetrahydrofuran / 20 °C View Scheme |