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CAS No.: | 13209-41-1 |
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Name: | 17,21-dihydroxy-16alpha-methylpregna-1,4,9(11)-triene-3,20-dione |
Article Data: | 10 |
Molecular Structure: | |
Formula: | C22H28 O4 |
Molecular Weight: | 356.462 |
Synonyms: | Pregna-1,4,9(11)-triene-3,20-dione,17,21-dihydroxy-16a-methyl- (6CI,7CI,8CI); 17a,21-Dihydroxy-16a-methylpregna-1,4,9(11)-triene-3,20-dione |
Density: | 1.24g/cm3 |
Melting Point: | 228-231 °C(Solv: acetone (67-64-1); hexane (110-54-3)) |
Boiling Point: | 548.3°C at 760 mmHg |
Flash Point: | 299.4°C |
PSA: | 74.60000 |
LogP: | 2.75290 |
(8S,10S,13S,14S,16R,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-7,8,12,14,15,16-hexahydro-6H-cyclopenta[a]phenanthren-3-one
Conditions | Yield |
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With hydrogenchloride In pentan-1-ol | 80% |
(8S,10S,13S,14S,16R,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-7,8,12,14,15,16-hexahydro-6H-cyclopenta[a]phenanthren-3-one
Conditions | Yield |
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Multi-step reaction with 2 steps 1: potassium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0 °C 2: hydrogenchloride / pentan-1-ol View Scheme |
2-((10S,13S,14S)-10,13-dimethyl-3-oxo-6,7,8,10,12,13,14,15-octahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl acetate
(8S,10S,13S,14S,16R,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-7,8,12,14,15,16-hexahydro-6H-cyclopenta[a]phenanthren-3-one
Conditions | Yield |
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Multi-step reaction with 3 steps 1.1: dichloromethane; tetrahydrofuran / 3 h / 20 °C / Inert atmosphere 1.2: 3 h / 20 °C / Inert atmosphere 1.3: -50 °C / Inert atmosphere 2.1: acetic acid; peracetic acid / toluene / 0.5 h / -10 °C / Inert atmosphere 3.1: potassium carbonate; water / methanol / 0 - 20 °C View Scheme |
17α,21-dihydroxy-16α-methyl-1,4,9(11)-pregnatriene-3,20-dione 21-acetate
(8S,10S,13S,14S,16R,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-7,8,12,14,15,16-hexahydro-6H-cyclopenta[a]phenanthren-3-one
Conditions | Yield |
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With water; potassium carbonate In methanol at 0 - 20℃; |
methanesulfonyl chloride
(8S,10S,13S,14S,16R,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-7,8,12,14,15,16-hexahydro-6H-cyclopenta[a]phenanthren-3-one
Methanesulfonic acid 2-((8S,10S,13S,14S,16R,17R)-17-hydroxy-10,13,16-trimethyl-3-oxo-6,7,8,10,12,13,14,15,16,17-decahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxo-ethyl ester
Conditions | Yield |
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With pyridine at 0 - 2℃; for 1.5h; | 85% |
formaldehyd
(8S,10S,13S,14S,16R,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-7,8,12,14,15,16-hexahydro-6H-cyclopenta[a]phenanthren-3-one
16α-methyl-17α,20;20,21-bismethylenedioxypregn-1,4,9(11)-triene-3-one
Conditions | Yield |
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With hydrogenchloride In dichloromethane Ambient temperature; | 74% |
methanesulfonyl chloride
(8S,10S,13S,14S,16R,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-7,8,12,14,15,16-hexahydro-6H-cyclopenta[a]phenanthren-3-one
Conditions | Yield |
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With dmap In dichloromethane for 4h; Heating; | A 69% B 1.1% |
(8S,10S,13S,14S,16R,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-7,8,12,14,15,16-hexahydro-6H-cyclopenta[a]phenanthren-3-one
Conditions | Yield |
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With dmap; methanesulfonyl chloride In dichloromethane for 4h; Heating; | A 69% B 1.1% |
(8S,10S,13S,14S,16R,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-7,8,12,14,15,16-hexahydro-6H-cyclopenta[a]phenanthren-3-one
Conditions | Yield |
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With Vilsmeier reagent; water 1.) toluene, from -3 deg C to 2 deg C, 3 h, 2.) toluene, 5 deg C; Yield given. Multistep reaction; |
(8S,10S,13S,14S,16R,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-7,8,12,14,15,16-hexahydro-6H-cyclopenta[a]phenanthren-3-one
21-fluoro-17α-hydroxy-16α-methyl-1,4,9(11)-ppregnatriene-3,30-dione 17-(2'-furoate)
Conditions | Yield |
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Multi-step reaction with 3 steps 1: 85 percent / pyridine / 1.5 h / 0 - 2 °C 2: 70 percent / KF / dimethylformamide / 4 h / 124 °C 3: 23 percent / 4-DMAP / CH2Cl2 / 27 h / 40 °C View Scheme | |
Multi-step reaction with 3 steps 1: 85 percent / pyridine / 1.5 h / 0 - 2 °C 2: 70 percent / KF / dimethylformamide / 4 h / 124 °C 3: 58 percent / 4-DMAP / CH2Cl2 / 20 h / Ambient temperature View Scheme |