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1343403-10-0

Basic Information
CAS No.: 1343403-10-0
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:
Molecular Structure of 1343403-10-0 ((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)
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
Synthetic route

micheliolide

1343403-10-0

(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
ConditionsYield
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 dichloromethane75%

micheliolide

A

1343403-10-0

(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

B

(3aS,5S,9R,9aS,9bS)-5,9-dihydroxy-6,9-dimethyl-3-methylene-3a,4,5,7,8,9,9a,9b-octahydroazuleno[4,5-b]furan-2(3H)-one

C

(3aS,6R,9R,9aS,9bS)-6,9-dihydroxy-6,9-dimethyl-3-methylene-3a,4,5,6,8,9,9a,9b-octahydroazuleno[4,5-b]furan-2(3H)-one

Conditions
ConditionsYield
With tert.-butylhydroperoxide; selenium(IV) oxide In dichloromethane; water for 3h;A 14%
B 53%
C 7%
503551-53-9

parthenolide

1343403-10-0

(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
ConditionsYield
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

5β-epoxy-germacra-1-(10),11-(13)-dien-12,6α-olide

1343403-10-0

(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
ConditionsYield
Multi-step reaction with 2 steps
1: toluene-4-sulfonic acid / dichloromethane
2: 3-chloro-benzenecarboperoxoic acid / dichloromethane
View Scheme
503551-53-9

parthenolide

A

1343403-10-0

(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

B

(3aS,5S,9R,9aS,9bS)-5,9-dihydroxy-6,9-dimethyl-3-methylene-3a,4,5,7,8,9,9a,9b-octahydroazuleno[4,5-b]furan-2(3H)-one

C

(3aS,6R,9R,9aS,9bS)-6,9-dihydroxy-6,9-dimethyl-3-methylene-3a,4,5,6,8,9,9a,9b-octahydroazuleno[4,5-b]furan-2(3H)-one

Conditions
ConditionsYield
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
1343403-10-0

(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

124-40-3

dimethyl amine

C17H27NO4

Conditions
ConditionsYield
With potassium carbonate In tetrahydrofuran; water at 20℃;96%
1343403-10-0

(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

53170-19-7

d6-dimethylamine hydrochloride

C17H21(2)H6NO4

Conditions
ConditionsYield
With potassium carbonate In tetrahydrofuran at 20℃;90%
1343403-10-0

(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

137624-14-7, 84692-91-1

1β,10β-Epoxyguaia-3,11(13)-dien-12,6α-olide

Conditions
ConditionsYield
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%
1343403-10-0

(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

C17H19(2)H6NO3

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: pyridine; trichlorophosphate / 2 h / 0 °C
2: potassium carbonate / tetrahydrofuran / 20 °C
View Scheme
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