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CAS No.: | 1879-77-2 |
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Name: | doxibetasol |
Article Data: | 3 |
Molecular Structure: | |
Formula: | C22H29 F O4 |
Molecular Weight: | 376.468 |
Synonyms: | Pregna-1,4-diene-3,20-dione,9-fluoro-11b,17-dihydroxy-16b-methyl- (7CI,8CI); 21-Deoxybetamethasone;9-Fluoro-11b,17-dihydroxy-16b-methylpregna-1,4-diene-3,20-dione;Doxibetasol |
Density: | 1.25g/cm3 |
Melting Point: | 230 - 234 °C |
Boiling Point: | 527.1°Cat760mmHg |
Flash Point: | 272.6°C |
PSA: | 74.60000 |
LogP: | 2.92330 |
16β-methyl-9α-fluoro-11β,17α-dihydroxy-1,4-pregnadiene-3,20-dione
Conditions | Yield |
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With bismuth(III) oxide; N-ethyl-N,N-diisopropylamine; para-thiocresol In dichloromethane for 2h; Irradiation; | 92% |
16β-methyl-9β,11β-epoxy-17α-hydroxy-1,4-pregnadiene-3,20-dione
16β-methyl-9α-fluoro-11β,17α-dihydroxy-1,4-pregnadiene-3,20-dione
Conditions | Yield |
---|---|
With hydrogen fluoride In tetrahydrofuran; dichloromethane at -70 - 0℃; for 5h; | 80% |
16α,17α-epoxy-3β-hydroxy-5α-pregn-9(11)-en-20-one
16β-methyl-9α-fluoro-11β,17α-dihydroxy-1,4-pregnadiene-3,20-dione
Conditions | Yield |
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Multi-step reaction with 6 steps 1.1: 95 percent / pyridine / 20 °C 2.1: 70 percent / triethyl orthoformate; p-toluenesulfonic acid / CH2Cl2 / 20 h / 20 °C 3.1: 72 percent / tetrahydrofuran; diethyl ether / 72 h / 60 °C 4.1: m-iodoxybenzoic acid; diphenyl diselenide / toluene / 22 h / Heating 4.2: 50 percent / p-toluenesulfonic acid / CH2Cl2 / 4 h / 20 °C 5.1: perchloric acid; 1,3-dibromo-5,5-dimethylhydantoin / dimethylformamide / 3 h / cooling 5.2: 75.8 percent / sodium hydroxide / CH2Cl2; methanol; H2O / 2 h / cooling 6.1: 80 percent / hydrofluoric acid / tetrahydrofuran; CH2Cl2 / 5 h / -70 - 0 °C View Scheme |
16β-methyl-3β,17α-dihydroxy-20,20-ethylenedioxy-5α-pregn-9(11)-ene
16β-methyl-9α-fluoro-11β,17α-dihydroxy-1,4-pregnadiene-3,20-dione
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: m-iodoxybenzoic acid; diphenyl diselenide / toluene / 22 h / Heating 1.2: 50 percent / p-toluenesulfonic acid / CH2Cl2 / 4 h / 20 °C 2.1: perchloric acid; 1,3-dibromo-5,5-dimethylhydantoin / dimethylformamide / 3 h / cooling 2.2: 75.8 percent / sodium hydroxide / CH2Cl2; methanol; H2O / 2 h / cooling 3.1: 80 percent / hydrofluoric acid / tetrahydrofuran; CH2Cl2 / 5 h / -70 - 0 °C View Scheme |
3β-acetoxy-16α,17α-epoxy-20,20-ethylenedioxy-5α-pregn-9(11)-ene
16β-methyl-9α-fluoro-11β,17α-dihydroxy-1,4-pregnadiene-3,20-dione
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: 72 percent / tetrahydrofuran; diethyl ether / 72 h / 60 °C 2.1: m-iodoxybenzoic acid; diphenyl diselenide / toluene / 22 h / Heating 2.2: 50 percent / p-toluenesulfonic acid / CH2Cl2 / 4 h / 20 °C 3.1: perchloric acid; 1,3-dibromo-5,5-dimethylhydantoin / dimethylformamide / 3 h / cooling 3.2: 75.8 percent / sodium hydroxide / CH2Cl2; methanol; H2O / 2 h / cooling 4.1: 80 percent / hydrofluoric acid / tetrahydrofuran; CH2Cl2 / 5 h / -70 - 0 °C View Scheme |
16β-methyl-17α-hydroxy-pregna-1,4,9(11)-triene-3,20-dione
16β-methyl-9α-fluoro-11β,17α-dihydroxy-1,4-pregnadiene-3,20-dione
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: perchloric acid; 1,3-dibromo-5,5-dimethylhydantoin / dimethylformamide / 3 h / cooling 1.2: 75.8 percent / sodium hydroxide / CH2Cl2; methanol; H2O / 2 h / cooling 2.1: 80 percent / hydrofluoric acid / tetrahydrofuran; CH2Cl2 / 5 h / -70 - 0 °C View Scheme |
20-oxo-5α-pregna-9(11),16-dien-3β-yl acetate
16β-methyl-9α-fluoro-11β,17α-dihydroxy-1,4-pregnadiene-3,20-dione
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1.1: 91.7 percent / hydrogen peroxide; sodium hydroxide / methanol / 2 h / 20 °C 2.1: 95 percent / pyridine / 20 °C 3.1: 70 percent / triethyl orthoformate; p-toluenesulfonic acid / CH2Cl2 / 20 h / 20 °C 4.1: 72 percent / tetrahydrofuran; diethyl ether / 72 h / 60 °C 5.1: m-iodoxybenzoic acid; diphenyl diselenide / toluene / 22 h / Heating 5.2: 50 percent / p-toluenesulfonic acid / CH2Cl2 / 4 h / 20 °C 6.1: perchloric acid; 1,3-dibromo-5,5-dimethylhydantoin / dimethylformamide / 3 h / cooling 6.2: 75.8 percent / sodium hydroxide / CH2Cl2; methanol; H2O / 2 h / cooling 7.1: 80 percent / hydrofluoric acid / tetrahydrofuran; CH2Cl2 / 5 h / -70 - 0 °C View Scheme |
Δ9(11)22-isoallospirosten-3β-ol
16β-methyl-9α-fluoro-11β,17α-dihydroxy-1,4-pregnadiene-3,20-dione
Conditions | Yield |
---|---|
Multi-step reaction with 8 steps 1.1: pyridine; ammonium chloride / 125 - 135 °C 1.2: acetic acid; chromium trioxide / H2O; 1,2-dichloro-ethane / 1 h / 20 °C 1.3: 57 percent / aluminium oxide / benzene / 2 h 2.1: 91.7 percent / hydrogen peroxide; sodium hydroxide / methanol / 2 h / 20 °C 3.1: 95 percent / pyridine / 20 °C 4.1: 70 percent / triethyl orthoformate; p-toluenesulfonic acid / CH2Cl2 / 20 h / 20 °C 5.1: 72 percent / tetrahydrofuran; diethyl ether / 72 h / 60 °C 6.1: m-iodoxybenzoic acid; diphenyl diselenide / toluene / 22 h / Heating 6.2: 50 percent / p-toluenesulfonic acid / CH2Cl2 / 4 h / 20 °C 7.1: perchloric acid; 1,3-dibromo-5,5-dimethylhydantoin / dimethylformamide / 3 h / cooling 7.2: 75.8 percent / sodium hydroxide / CH2Cl2; methanol; H2O / 2 h / cooling 8.1: 80 percent / hydrofluoric acid / tetrahydrofuran; CH2Cl2 / 5 h / -70 - 0 °C View Scheme |
3β-acetoxy-16α,17α-epoxy-5α-pregn-9(11)-en-20-one
16β-methyl-9α-fluoro-11β,17α-dihydroxy-1,4-pregnadiene-3,20-dione
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: 70 percent / triethyl orthoformate; p-toluenesulfonic acid / CH2Cl2 / 20 h / 20 °C 2.1: 72 percent / tetrahydrofuran; diethyl ether / 72 h / 60 °C 3.1: m-iodoxybenzoic acid; diphenyl diselenide / toluene / 22 h / Heating 3.2: 50 percent / p-toluenesulfonic acid / CH2Cl2 / 4 h / 20 °C 4.1: perchloric acid; 1,3-dibromo-5,5-dimethylhydantoin / dimethylformamide / 3 h / cooling 4.2: 75.8 percent / sodium hydroxide / CH2Cl2; methanol; H2O / 2 h / cooling 5.1: 80 percent / hydrofluoric acid / tetrahydrofuran; CH2Cl2 / 5 h / -70 - 0 °C View Scheme |
Δ9(11)22-isoallospirosten-3β-ol-12-one-3-acetate
16β-methyl-9α-fluoro-11β,17α-dihydroxy-1,4-pregnadiene-3,20-dione
Conditions | Yield |
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Multi-step reaction with 9 steps 1.1: hydrazine hydrate / ethane-1,2-diol / 1 h / Heating 1.2: 95 percent / potassium hydroxide / ethane-1,2-diol; H2O / 5 h / 195 - 197 °C 2.1: pyridine; ammonium chloride / 125 - 135 °C 2.2: acetic acid; chromium trioxide / H2O; 1,2-dichloro-ethane / 1 h / 20 °C 2.3: 57 percent / aluminium oxide / benzene / 2 h 3.1: 91.7 percent / hydrogen peroxide; sodium hydroxide / methanol / 2 h / 20 °C 4.1: 95 percent / pyridine / 20 °C 5.1: 70 percent / triethyl orthoformate; p-toluenesulfonic acid / CH2Cl2 / 20 h / 20 °C 6.1: 72 percent / tetrahydrofuran; diethyl ether / 72 h / 60 °C 7.1: m-iodoxybenzoic acid; diphenyl diselenide / toluene / 22 h / Heating 7.2: 50 percent / p-toluenesulfonic acid / CH2Cl2 / 4 h / 20 °C 8.1: perchloric acid; 1,3-dibromo-5,5-dimethylhydantoin / dimethylformamide / 3 h / cooling 8.2: 75.8 percent / sodium hydroxide / CH2Cl2; methanol; H2O / 2 h / cooling 9.1: 80 percent / hydrofluoric acid / tetrahydrofuran; CH2Cl2 / 5 h / -70 - 0 °C View Scheme |