flumetasone
Conditions | Yield |
---|---|
With monoperoxyphthalic acid In dichloromethane; ethyl acetate at 27℃; | 93% |
Conditions | Yield |
---|---|
With Curvularia lunata In water at 30℃; for 72h; Yield given; |
B
flumetasone
Conditions | Yield |
---|---|
With pyridine In propionic acid anhydride |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: potassium carbonate; water / methanol / 10 h 2: hydrogen fluoride / 5 h / -15 - -10 °C View Scheme |
flumetasone
Conditions | Yield |
---|---|
With hydrogen fluoride at -15 - -10℃; for 5h; |
flumetasone
6α,9α-difluoro-11β,17α-dihydroxy-16α-methyl-3-oxoandrosta-1,4-diene-17β-carboxylic acid
Conditions | Yield |
---|---|
With water; periodic acid In tetrahydrofuran at 20℃; for 1h; | 100% |
With periodic acid In tetrahydrofuran; water at 0 - 20℃; for 2h; | 99.12% |
With periodic acid In tetrahydrofuran; water at 0 - 20℃; for 5.75h; | 98% |
2-(triphenylmethylthio)ethanoic acid
flumetasone
Conditions | Yield |
---|---|
With dmap In dichloromethane at 20℃; | 98% |
flumetasone
Conditions | Yield |
---|---|
With pyridine; N-Bromosuccinimide; sulfur dioxide at 20℃; for 1h; | 97.3% |
flumetasone
6α,9-difluoro-11β,21-dihydroxy-16α-methylpregna-1,4-diene-3,20-dione
Conditions | Yield |
---|---|
With trimethylsilyl iodide In acetonitrile at -20℃; for 2h; Inert atmosphere; | 93% |
flumetasone
Triethyl orthopropionate
6α,9α-difluoro-11β,17,21-trihydroxy-16α-methylpregna-1,4-diene-3,20-dione cyclic 17,21-(ethyl orthopropionate)
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In N,N-dimethyl-formamide; toluene at 20℃; for 2h; | 90% |
flumetasone
6α,9α-difluoro-11β-hydroxy-16α-methylandrosta-1,4-diene-3,17-dione
Conditions | Yield |
---|---|
In acetonitrile for 1h; Irradiation; | 50 % Turnov. |
flumetasone
A
6α,9α-difluoro-11β-hydroxy-16α-methylandrosta-1,4-diene-3,17-dione
B
6α,9α-difluoro-11β,17α,21-trihydroxy-16α-methyl-1,5-cyclopregna-3-ene-2,20-dione
Conditions | Yield |
---|---|
In acetonitrile Quantum yield; Further Variations:; irradiation wavelength; UV-irradiation; | |
In acetonitrile Quantum yield; Further Variations:; irradiation wavelength; Irradiation; |
flumetasone
6α,9α-difluoro-11β,17α,21-trihydroxy-16α-methyl-1,5-cyclopregna-3-ene-2,20-dione
Conditions | Yield |
---|---|
In acetonitrile for 2.5h; Irradiation; | 60 % Turnov. |
flumetasone
6α,9α-difluoro-11β,21-dihydroxy-16α-methyl-17α-propionyloxypregna-1,4-diene-3,20-dione
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 90 percent / TsOH / dimethylformamide; toluene / 2 h / 20 °C 2: 96 percent / aq. AcOH / methanol / 0.5 h / Heating View Scheme |
flumetasone
6α,9α-difluoro-11β,21-dihydroxy-16α-methyl-17α-propionyloxypregn-4-ene-3,20-dione
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 90 percent / TsOH / dimethylformamide; toluene / 2 h / 20 °C 2: 96 percent / aq. AcOH / methanol / 0.5 h / Heating 3: 85 percent / H2 / (Ph3P)3RhCl / ethanol / 60 h / 760.05 Torr View Scheme |
flumetasone
6α,9α-difluoro-11β-hydroxy-21-methylsulfonyloxy-16α-methyl-17α-propionyloxypregna-1,4-diene-3,20-dione
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 90 percent / TsOH / dimethylformamide; toluene / 2 h / 20 °C 2: 96 percent / aq. AcOH / methanol / 0.5 h / Heating 3: 100 percent / pyridine / 2 h View Scheme |
flumetasone
6α,9α-difluoro-11β-hydroxy-21-methylsulfonyloxy-16α-methyl-17α-propionyloxypregn-4-ene-3,20-dione
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 90 percent / TsOH / dimethylformamide; toluene / 2 h / 20 °C 2: 96 percent / aq. AcOH / methanol / 0.5 h / Heating 3: 85 percent / H2 / (Ph3P)3RhCl / ethanol / 60 h / 760.05 Torr 4: 100 percent / pyridine / 2 h View Scheme |
flumetasone
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: 90 percent / TsOH / dimethylformamide; toluene / 2 h / 20 °C 2.1: 96 percent / aq. AcOH / methanol / 0.5 h / Heating 3.1: 100 percent / pyridine / 2 h 4.1: NaH / tetrahydrofuran / 0.5 h / 0 °C 4.2: 17 percent / tetrahydrofuran / 22 h / 0 - 21 °C View Scheme |
flumetasone
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: 90 percent / TsOH / dimethylformamide; toluene / 2 h / 20 °C 2.1: 96 percent / aq. AcOH / methanol / 0.5 h / Heating 3.1: 85 percent / H2 / (Ph3P)3RhCl / ethanol / 60 h / 760.05 Torr 4.1: 100 percent / pyridine / 2 h 5.1: NaH / tetrahydrofuran / 0.5 h / 0 °C 5.2: 43 percent / tetrahydrofuran / 22 h / 0 - 21 °C View Scheme |
Conditions | Yield |
---|---|
toluene-4-sulfonic acid In N,N-dimethyl-formamide at 20℃; for 72h; |
methanesulfonyl chloride
flumetasone
2-[(1R,2S,8S,10S,11S,13R,14R,15S,17S)-1,8-difluoro-14,17-dihydroxy-2,13,15-trimethyl-5-oxotetracyclo[8.7.0.02'7.011,15]heptadeca-3,6-dien-14-yl]-2-oxoethyl methanesulfonate
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; | |
With pyridine at 0℃; for 2h; |
flumetasone
C29H31F2NO4S2
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0 - 20 °C 2: potassium carbonate / acetone / Reflux View Scheme |
flumetasone
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: periodic acid / 1,4-dioxane; water / 2 h / 20 °C 2: triethylamine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 18 h / 0 - 20 °C / Inert atmosphere View Scheme |
flumetasone
C53H87F2N3O13
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: periodic acid / 1,4-dioxane; water / 2 h / 20 °C 2: triethylamine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 18 h / 0 - 20 °C / Inert atmosphere View Scheme |
Conditions | Yield |
---|---|
With acetic acid In ethanol; water at 70℃; for 0.5h; |
flumetasone
6α,9α-difluoro-11β-hydroxy-16α-methyl-3-oxo-17α-(propionyloxy)androsta-1,4-diene-17β-carboxylic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: sodium periodate / water; tetrahydrofuran / 2 h / 25 - 30 °C 2.1: triethylamine / acetone / 3 h / 0 - 5 °C 2.2: 2.5 h / 40 - 45 °C View Scheme | |
Multi-step reaction with 2 steps 1.1: periodic acid / water; tetrahydrofuran / 2 h / 0 - 10 °C 2.1: triethylamine / acetone / 1 h / 0 - 10 °C 2.2: 2 h View Scheme |
flumetasone
17β-[(N,N-dimethylcarbamoyl)thio]formyl-6α,9α-difluoro-11β-hydroxy-16α-methyl-17α-propionyloxy-3-one androstone-1,4-diene
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: sodium periodate / water; tetrahydrofuran / 2 h / 25 - 30 °C 2.1: triethylamine / acetone / 3 h / 0 - 5 °C 2.2: 2.5 h / 40 - 45 °C 3.1: sodium iodide; triethylamine / tetrahydrofuran / 4 h / 70 - 75 °C View Scheme | |
Multi-step reaction with 3 steps 1.1: periodic acid / water; tetrahydrofuran / 2 h / 0 - 10 °C 2.1: triethylamine / acetone / 1 h / 0 - 10 °C 2.2: 2 h 3.1: sodium iodide; triethylamine / tetrahydrofuran / 16 h / 20 °C View Scheme |
flumetasone
17-propionate carbothioic acid
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: sodium periodate / water; tetrahydrofuran / 2 h / 25 - 30 °C 2.1: triethylamine / acetone / 3 h / 0 - 5 °C 2.2: 2.5 h / 40 - 45 °C 3.1: sodium iodide; triethylamine / tetrahydrofuran / 4 h / 70 - 75 °C 4.1: morpholine / 3 h / 20 °C View Scheme | |
Multi-step reaction with 4 steps 1.1: periodic acid / water; tetrahydrofuran / 2 h / 0 - 10 °C 2.1: triethylamine / acetone / 1 h / 0 - 10 °C 2.2: 2 h 3.1: sodium iodide; triethylamine / tetrahydrofuran / 16 h / 20 °C 4.1: calcium hydroxide / methanol / 24 h / 25 - 30 °C View Scheme |
flumetasone
flixotide
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: sodium periodate / water; tetrahydrofuran / 2 h / 25 - 30 °C 2.1: triethylamine / acetone / 3 h / 0 - 5 °C 2.2: 2.5 h / 40 - 45 °C 3.1: sodium iodide; triethylamine / tetrahydrofuran / 4 h / 70 - 75 °C 4.1: morpholine / 3 h / 20 °C 5.1: potassium carbonate / acetone / 0.5 h / 20 °C 5.2: 0 - 5 °C View Scheme |
1. Introduction of Flumethasone
Flumethasone is an odorless, white to creamy white, crystalline powder. The IUPAC name is (6S,8S,9R,10S,11S,13S,14S,16R,17R)-6,9-difluoro-11,17-dihydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-3-one.
2. Properties of Flumethasone
H bond acceptors: 5
H bond donors: 3
Freely Rotating Bonds: 5
Polar Surface Area: 61.83 Å2
Index of Refraction: 1.579
Molar Refractivity: 100.33 cm3
Molar Volume: 301.7 cm3
Surface Tension: 54.3 dyne/cm
Density: 1.36 g/cm3
Flash Point: 298.4 °C
Enthalpy of Vaporization: 98.19 kJ/mol
Boiling Point: 569.8 °C at 760 mmHg
Vapour Pressure: 2.33E-15 mmHg at 25°C
Storage temp.: 2-8°C
3. Structure Descriptors of Flumethasone
SMILES: O=C(CO)[C@]3(O)[C@]2(C[C@H](O)[C@]4(F)[C@@]/1(\C(=C/C(=O)\C=C\1)[C@@H](F)C[C@H]4[C@@H]2C[C@H]3C)C)C
InChI: InChI=1/C22H28F2O5/c1-11-6-13-14-8-16(23)15-7-12(26)4-5-19(15,2)21(14,24)17(27)9-20(13,3)22(11,29)18(28)10-25/h4-5,7,11,13-14,16-17,25,27,29H,6,8-10H2,1-3H3/t11-,13+,14+,16+,17+,19+,20+,21+,22+/m1/s1 Copy
InChIKey: WXURHACBFYSXBI-GQKYHHCABT
Std. InChI: InChI=1S/C22H28F2O5/c1-11-6-13-14-8-16(23)15-7-12(26)4-5-19(15,2)21(14,24)17(27)9-20(13,3)22(11,29)18(28)10-25/h4-5,7,11,13-14,16-17,25,27,29H,6,8-10H2,1-3H3/t11-,13+,14+,16+,17+,19+,20+,21+,22+/m1/s1
Std. InChIKey: WXURHACBFYSXBI-GQKYHHCASA-N
4. Safety Information of Flumethasone
Hazard Codes: Xn
Risk Statements: 40
40: Limited evidence of a carcinogenic effect
Safety Statements: 22-36
22: Do not breathe dust
36: Wear suitable protective clothing
WGK Germany: 3
RTECS: TU3832000
Experimental reproductive effects. When heated to decomposition it emits toxic fumes of F−.
5. Use of Flumethasone
Flumethasone is a glucocorticoid. It is an anti-inflammatory and a corticosteroid for topical use. Besides, flumethasone is also used for the treatment of otitis externa and otomycosis.
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