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1879-77-2

Basic Information
CAS No.: 1879-77-2
Name: doxibetasol
Article Data: 3
Molecular Structure:
Molecular Structure of 1879-77-2 (doxibetasol)
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
Synthetic route

C22H28FIO4

1879-77-2

16β-methyl-9α-fluoro-11β,17α-dihydroxy-1,4-pregnadiene-3,20-dione

Conditions
ConditionsYield
With bismuth(III) oxide; N-ethyl-N,N-diisopropylamine; para-thiocresol In dichloromethane for 2h; Irradiation;92%
37413-99-3

16β-methyl-9β,11β-epoxy-17α-hydroxy-1,4-pregnadiene-3,20-dione

1879-77-2

16β-methyl-9α-fluoro-11β,17α-dihydroxy-1,4-pregnadiene-3,20-dione

Conditions
ConditionsYield
With hydrogen fluoride In tetrahydrofuran; dichloromethane at -70 - 0℃; for 5h;80%
884488-47-5

16α,17α-epoxy-3β-hydroxy-5α-pregn-9(11)-en-20-one

1879-77-2

16β-methyl-9α-fluoro-11β,17α-dihydroxy-1,4-pregnadiene-3,20-dione

Conditions
ConditionsYield
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
884488-49-7

16β-methyl-3β,17α-dihydroxy-20,20-ethylenedioxy-5α-pregn-9(11)-ene

1879-77-2

16β-methyl-9α-fluoro-11β,17α-dihydroxy-1,4-pregnadiene-3,20-dione

Conditions
ConditionsYield
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
884488-48-6

3β-acetoxy-16α,17α-epoxy-20,20-ethylenedioxy-5α-pregn-9(11)-ene

1879-77-2

16β-methyl-9α-fluoro-11β,17α-dihydroxy-1,4-pregnadiene-3,20-dione

Conditions
ConditionsYield
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
14135-32-1

16β-methyl-17α-hydroxy-pregna-1,4,9(11)-triene-3,20-dione

1879-77-2

16β-methyl-9α-fluoro-11β,17α-dihydroxy-1,4-pregnadiene-3,20-dione

Conditions
ConditionsYield
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
21650-83-9

20-oxo-5α-pregna-9(11),16-dien-3β-yl acetate

1879-77-2

16β-methyl-9α-fluoro-11β,17α-dihydroxy-1,4-pregnadiene-3,20-dione

Conditions
ConditionsYield
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
1106-20-3

Δ9(11)22-isoallospirosten-3β-ol

1879-77-2

16β-methyl-9α-fluoro-11β,17α-dihydroxy-1,4-pregnadiene-3,20-dione

Conditions
ConditionsYield
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
113926-56-0

3β-acetoxy-16α,17α-epoxy-5α-pregn-9(11)-en-20-one

1879-77-2

16β-methyl-9α-fluoro-11β,17α-dihydroxy-1,4-pregnadiene-3,20-dione

Conditions
ConditionsYield
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
989-73-1

Δ9(11)22-isoallospirosten-3β-ol-12-one-3-acetate

1879-77-2

16β-methyl-9α-fluoro-11β,17α-dihydroxy-1,4-pregnadiene-3,20-dione

Conditions
ConditionsYield
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
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    1879-77-2

    Pregna-1,4-diene-3,20-dione,9-fluoro-11,17-dihydroxy-16-methyl-, (11b,16b)-

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