Conditions | Yield |
---|---|
Stage #1: methyl bromide With magnesium In tetrahydrofuran at 40 - 45℃; Stage #2: Androsta-1,4-diene-3,17-dione In toluene at 50 - 55℃; | 94.6% |
Stage #1: methyl bromide With magnesium In tetrahydrofuran at 40 - 45℃; Stage #2: Androsta-1,4-diene-3,17-dione In toluene at 50 - 55℃; | 94.6% |
Stage #1: methyl bromide With magnesium In tetrahydrofuran at 40 - 45℃; Stage #2: Androsta-1,4-diene-3,17-dione In toluene at 50 - 55℃; Stage #3: With hydrogenchloride In water at 50 - 55℃; pH=2 - 3; | 93.8% |
Conditions | Yield |
---|---|
Stage #1: methylene chloride With magnesium In tetrahydrofuran at 30 - 35℃; Stage #2: Androsta-1,4-diene-3,17-dione In tetrahydrofuran at 50 - 55℃; | 92.5% |
Stage #1: methylene chloride With magnesium In tetrahydrofuran at 30 - 35℃; Stage #2: Androsta-1,4-diene-3,17-dione In tetrahydrofuran at 50 - 55℃; | 92.5% |
Stage #1: methylene chloride With magnesium In tetrahydrofuran at 30 - 35℃; Stage #2: Androsta-1,4-diene-3,17-dione In tetrahydrofuran at 50 - 55℃; Stage #3: With hydrogenchloride In water at 50 - 55℃; pH=2 - 3; | 92.5% |
Conditions | Yield |
---|---|
Stage #1: methyl iodide With magnesium In diethyl ether at 30 - 35℃; Stage #2: Androsta-1,4-diene-3,17-dione In benzene at 50 - 55℃; | 90.8% |
Stage #1: methyl iodide With magnesium In diethyl ether at 30 - 35℃; Stage #2: Androsta-1,4-diene-3,17-dione In benzene at 50 - 55℃; | 90.8% |
Stage #1: methyl iodide With magnesium In diethyl ether at 30 - 35℃; Stage #2: Androsta-1,4-diene-3,17-dione In benzene at 50 - 55℃; Stage #3: With hydrogenchloride In water at 50 - 55℃; pH=2 - 3; | 90.8% |
Conditions | Yield |
---|---|
With tert-butyldimethylsilyl chloride; 2,3-dicyano-5,6-dichloro-p-benzoquinone In 1,4-dioxane at 0 - 20℃; for 48h; | 78% |
With selenium(IV) oxide | |
mit Hilfe von Didymella lycopersici; |
Conditions | Yield |
---|---|
With dmap; triethylamine In dichloromethane at 0 - 20℃; for 12h; Inert atmosphere; | 95% |
metandienone
(8S,9S,10R,13S,14S)-10,13,17-trimethyl-7,8,9,11,12,13,14,15-octahydro-6H-cyclopenta[a]phenanthren-3(10H)-one
Conditions | Yield |
---|---|
With Amberlyst-15 In dichloromethane at 20℃; for 6h; | 90% |
metandienone
B
6β,17β-dihydroxy-17α-methyl-1,4-androstadien-3-one
Conditions | Yield |
---|---|
With Penicillium notatum KCH 904 In water; acetone at 27℃; for 264h; Enzymatic reaction; | A 83% B 9% |
Conditions | Yield |
---|---|
With cerium(III) chloride; tetrabutyl-ammonium chloride In acetonitrile for 48h; Inert atmosphere; Irradiation; diastereoselective reaction; | 71% |
metandienone
17,17-dimethyl-18-norandrosta-1,4,13(14)-trien-3-one
Conditions | Yield |
---|---|
With hydrogenchloride at 60℃; for 0.5h; | 60% |
With hydrogenchloride In methanol; water for 16h; Reflux; |
metandienone
Conditions | Yield |
---|---|
Stage #1: metandienone With C19H26ClIrN3O(1+)*Cl(1-) In water; acetonitrile at 80℃; for 0.166667h; Green chemistry; Stage #2: With formic acid In water; acetonitrile at 80℃; for 4h; Green chemistry; | 35% |
Conditions | Yield |
---|---|
With thallium(III) nitrate trihydrate In diethylene glycol dimethyl ether for 24h; Ambient temperature; | 34% |
metandienone
UDP-glucuronic acid
A
17β-methyl-5β-androst-1-ene-17α-ol-3α-O-glucuronide
Conditions | Yield |
---|---|
With liver microsomes from Aroclor 1254-induced male Wistar rat In methanol; phosphate buffer at 37℃; pH=7.4; | A 25% B n/a |
metandienone
Conditions | Yield |
---|---|
With axenic culture of strain T76 Scenedesmus quadricauda | A 11% B 21% |
With axenic culture of strain T76 of Scenedesmus quadricauda | A 11% B 21% |
metandienone
Conditions | Yield |
---|---|
(i) MeNH2, MeOH, (ii) aq. Ca(OCl)2, NH3, NH4Cl; Multistep reaction; |
Conditions | Yield |
---|---|
With chlorosulfonic acid 1.) -5 deg C, 2.) RT, 3 h; Yield given. Multistep reaction; |
metandienone
metanedienone-17-sulfate
Conditions | Yield |
---|---|
With sulfur trioxide pyridine complex In N,N-dimethyl-formamide for 12h; Ambient temperature; | 3.8 g |
N-methyl-N-trimethylsilyl-2,2,2-trifluoroacetamide
metandienone
(8R,9S,10R,13S,14S,17S)-10,13,17-Trimethyl-3,17-bis-trimethylsilanyloxy-8,9,10,11,12,13,14,15,16,17-decahydro-7H-cyclopenta[a]phenanthrene
Conditions | Yield |
---|---|
With ammonium iodide In ethyl acetate for 1h; Heating; | 97 % Chromat. |
With ammonium iodide; 2-hydroxyethanethiol at 60℃; for 0.333333h; | |
With ammonium iodide; ethanethiol In acetonitrile at 80℃; for 0.5h; |
metandienone
3,5-Dioxo-17β-hydroxy-17α-methyl-10(5->4)-abeo-Δ1-androsten
Conditions | Yield |
---|---|
(i) PhCO3H, CHCl3, (ii) (UV-irradiation), dioxane; Multistep reaction; |
methanol
metandienone
1-Hydroxy-4.17.17-trimethyl-7.8.9.11.12.15.16.17-octahydro-6H-cyclopentaphenanthren
Conditions | Yield |
---|---|
With hydrogenchloride |
methanol
metandienone
13-Chlor-1-methoxy-4.17.17-trimethyl-13ξ-gonatrien-(A)
Conditions | Yield |
---|---|
With hydrogenchloride |
methanol
metandienone
17,17-dimethyl-18-norandrosta-1,4,13(14)-trien-3-one
Conditions | Yield |
---|---|
With hydrogenchloride |
Conditions | Yield |
---|---|
With potassium tert-butylate In dimethyl sulfoxide |
metandienone
Conditions | Yield |
---|---|
With water In 1,4-dioxane at 24℃; for 480h; Irradiation; green alga T76 Scenedesmus quadricauda; Yield given. Further byproducts given. Yields of byproduct given; |
metandienone
Conditions | Yield |
---|---|
In 1,4-dioxane at 24℃; for 480h; Irradiation; green alga T76 Scenedesmus quadricauda; Yield given. Further byproducts given. Yields of byproduct given; | |
With water In 1,4-dioxane at 24℃; for 480h; Irradiation; green alga T76 Scenedesmus quadricauda; Yield given. Further byproducts given. Yields of byproduct given; |
Conditions | Yield |
---|---|
With sodium tetrahydroborate In ethanol at 20℃; for 2h; |
metandienone
17α-17-hydroxy-17-methylandrosta-1,4-dien-3-one
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 3.8 g / sulfur trioxide pyridine complex / dimethylformamide / 12 h / Ambient temperature 2: H2O / 24 h View Scheme |
metandienone
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 3.8 g / sulfur trioxide pyridine complex / dimethylformamide / 12 h / Ambient temperature 2: H2O / 24 h 3: trimethylsilylimidazole / 0.17 h / 60 °C 4: trimethyliodosilane / 0.25 h / 60 °C View Scheme |
metandienone
(8R,9S,10R,13S,14S,17R)-10,13,17-Trimethyl-17-trimethylsilanyloxy-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-cyclopenta[a]phenanthren-3-one
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 3.8 g / sulfur trioxide pyridine complex / dimethylformamide / 12 h / Ambient temperature 2: H2O / 24 h 3: trimethylsilylimidazole / 0.17 h / 60 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: KOtBu / dimethylsulfoxide 2: NaBH4 / methanol View Scheme |
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