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9-alpha-hydroxyandrost-4-ene-3,17-dione
androst-4,9(11)-dien-3,17-dione
Conditions | Yield |
---|---|
In water; benzene | 97.5% |
In water; benzene | 97.5% |
With sulfuric acid; acetic acid In dichloromethane; water Reflux; | 95% |
Anecortave
androst-4,9(11)-dien-3,17-dione
Conditions | Yield |
---|---|
With sodium bismuthate | 87% |
With manganese(IV) oxide In chloroform for 4h; Heating; | 72.6% |
Conditions | Yield |
---|---|
With concentrated aqueous hydrochloric acid; p-TSA; sodium hydrogencarbonate In pyridine; water; benzene | 83.7% |
androst-5,9(11)-dien-3,17-dione-3,17-di-ethylene ketal
androst-4,9(11)-dien-3,17-dione
Conditions | Yield |
---|---|
With acetic acid In water at 110℃; for 0.333333h; | 71% |
With acetic acid Heating; | 70% |
(8S,9S,10R,11S,13S,14S)-11-Hydroxy-10,13-dimethyl-1,6,7,8,9,10,11,12,13,14,15,16-dodecahydro-2H-cyclopenta[a]phenanthrene-3,17-dione
androst-4,9(11)-dien-3,17-dione
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid; orthoformic acid triethyl ester In benzene Heating; | 50% |
With N,N'-Thionyldiimidazole In tetrahydrofuran for 0.5h; Ambient temperature; | 45% |
With hydrogenchloride; diethyl ether; benzene |
(8S,9S,10R,11S,13S,14S)-11-Hydroxy-10,13-dimethyl-1,6,7,8,9,10,11,12,13,14,15,16-dodecahydro-2H-cyclopenta[a]phenanthrene-3,17-dione
A
androst-4,9(11)-dien-3,17-dione
B
6β-hydroxy-4,9(11)-androstadiene-3,17-dione
Conditions | Yield |
---|---|
With ethanol; oxygen; toluene-4-sulfonic acid; orthoformic acid triethyl ester Product distribution; Irradiation; | A 35% B 12% |
With ethanol; oxygen; toluene-4-sulfonic acid; orthoformic acid triethyl ester 1.) 1 h, reflux; 2.) irradiation, ethanol, 3 h; Yield given. Multistep reaction. Yields of byproduct given; | |
With ethanol; oxygen; toluene-4-sulfonic acid; orthoformic acid triethyl ester 1.) 1 h, reflux, benzene; 2.) irradiation in ethanol, 3 h.; Yield given. Multistep reaction. Yields of byproduct given; |
Conditions | Yield |
---|---|
With bithmuth(III) triflate hydrate In nitromethane at 100℃; | 34% |
Multi-step reaction with 3 steps 1: 52 percent / MnO2 2: 48 percent / p-TsOH, triethyl orthoformate / benzene / 8 h / Heating 3: 70 percent / aq. AcOH / Heating View Scheme |
Conditions | Yield |
---|---|
With chromium(VI) oxide; acetic acid Oxidation; |
9-alpha-hydroxyandrost-4-ene-3,17-dione
A
androst-4,9(11)-dien-3,17-dione
Conditions | Yield |
---|---|
With N,N'-Thionyldiimidazole In tetrahydrofuran for 1.5h; Ambient temperature; Yield given. Yields of byproduct given. Title compound not separated from byproducts; |
(5R,8S,10R,13S,14S)-5-Hydroxy-10,13-dimethyl-1,4,5,6,7,8,10,12,13,14,15,16-dodecahydro-2H-cyclopenta[a]phenanthrene-3,17-dione
androst-4,9(11)-dien-3,17-dione
Conditions | Yield |
---|---|
With hydrogenchloride In methanol Heating; |
(8S,9S,10R,11S,13S,14S,17R)-17-((R)-1,2-dihydroxyethyl)-11,17-dihydroxy-10,13-dimethyl-6,7,8, 9,10,11,12,13,14,15,16, 17-dodecahydro-1H-cyclopenta[a] phenanthrene-3 (2H)-one
androst-4,9(11)-dien-3,17-dione
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: NaIO4 / 24 h / Ambient temperature 2: p-TsOH / benzene / 24 h / Heating View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 5.33 g / potassium carbonate / methanol; H2O / 1 h, room t., 50 min, 40 deg C 2: 87 percent / sodium bismutate View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: aqueous HCl 2: CrO3; acetic acid / Oxidation View Scheme |
(3R,5R,8S,10R,13S,14S,17S)-10,13-Dimethyl-1,2,3,4,6,7,8,10,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthrene-3,5,17-triol
androst-4,9(11)-dien-3,17-dione
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: CrO3, aq. H2SO4 / acetone 2: aq. HCl / methanol / Heating View Scheme |
(3S,5R,8S,10R,13S,14S,17S)-10,13-Dimethyl-1,2,3,4,6,7,8,10,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthrene-3,5,17-triol
androst-4,9(11)-dien-3,17-dione
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: CrO3, aq. H2SO4 / acetone 2: aq. HCl / methanol / Heating View Scheme |
(5R,8S,10R,13S,14S,17S)-5,17-Dihydroxy-10,13-dimethyl-1,2,4,5,6,7,8,10,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-3-one
androst-4,9(11)-dien-3,17-dione
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: CrO3, aq. H2SO4 / acetone 2: aq. HCl / methanol / Heating View Scheme |
androst-4,9(11)-dien-3,17-dione
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: aq. AcOH / Ambient temperature 2: CrO3, aq. H2SO4 / acetone 3: aq. HCl / methanol / Heating View Scheme |
androst-4,9(11)-dien-3,17-dione
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: (i) THF, (ii) aq. NH4Cl 2: CrO3, aq. H2SO4 / acetone 3: aq. HCl / methanol / Heating View Scheme |
androst-4,9(11)-dien-3,17-dione
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: (i) THF, (ii) aq. NH4Cl 2: CrO3, aq. H2SO4 / acetone 3: aq. HCl / methanol / Heating View Scheme |
9-alpha-hydroxyandrost-4-ene-3,17-dione
pyrographite
sodium sulfate
androst-4,9(11)-dien-3,17-dione
Conditions | Yield |
---|---|
With antimonypentachloride In dichloromethane; water | |
With antimonypentachloride In dichloromethane; water |
9α-hydroxy-3-methoxy-3,5-androstenedione-17-one
androst-4,9(11)-dien-3,17-dione
Conditions | Yield |
---|---|
In water; ethyl acetate; benzene | |
In water; ethyl acetate; benzene |
Conditions | Yield |
---|---|
With pyridine; p-TSA In chloroform; water; ethyl acetate |
androst-4,9(11)-dien-3,17-dione
Conditions | Yield |
---|---|
With hydrogenchloride; sodium hydrogencarbonate In pyridine; water; benzene | |
In ethyl acetate |
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In ethanol at 40℃; for 4h; Inert atmosphere; | 96% |
With toluene-4-sulfonic acid In tetrahydrofuran at 40℃; | 9 g |
androst-4,9(11)-dien-3,17-dione
2-hydroxy-2-methylpropanenitrile
17β-Cyano-17α-hydroxyandrosta-4,9(11)-dien-3-one
Conditions | Yield |
---|---|
In methanol at 40℃; for 2h; Solvent; Temperature; Time; | 92% |
In methanol; water | |
With potassium hydroxide In methanol; water Reagent/catalyst; Solvent; | 10.3 g |
Stage #1: androst-4,9(11)-dien-3,17-dione; 2-hydroxy-2-methylpropanenitrile With sodium hydroxide In methanol; water at 36 - 40℃; for 3h; Stage #2: In methanol; water at 20℃; for 2h; |
androst-4,9(11)-dien-3,17-dione
methyllithium
pregna-4,9(11)-diene-3,20-dione-17-hydroxy-21-methyl
Conditions | Yield |
---|---|
In acetone at 20℃; for 0.5h; | 90.6% |
Conditions | Yield |
---|---|
With acetic acid In ethanol for 4h; Heating; | 90% |
Conditions | Yield |
---|---|
With acetic acid In ethanol for 2.5h; Heating; | 90% |
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In toluene for 2h; Reflux; | 85% |
With toluene-4-sulfonic acid In toluene for 2h; Reflux; | 85% |
androst-4,9(11)-dien-3,17-dione
trimethyl orthoformate
3-methoxy-3,5,9(11)-androstatriene-17-dione
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In tetrahydrofuran at 20℃; for 2.5h; | 83% |
With pyridine; toluene-4-sulfonic acid; triethylamine In 1,4-dioxane; ethyl acetate | |
With toluene-4-sulfonic acid In 1,4-dioxane at 0 - 15℃; for 4.25h; Inert atmosphere; | 101 g |
With pyridine hydrochloride In methanol at 20℃; | 9.2 g |
androst-4,9(11)-dien-3,17-dione
9α,11α-epoxy-4-androstene-3,17-dione
Conditions | Yield |
---|---|
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at -20 - 0℃; for 24h; | 80% |
androst-4,9(11)-dien-3,17-dione
hydrazine carboxamide
Conditions | Yield |
---|---|
In ethanol Reflux; | A 76% B n/a C n/a |
Conditions | Yield |
---|---|
With sodium tetrahydroborate In pyridine; methanol | 71% |
With zygowilliopsis sp. WY7905 In aq. phosphate buffer at 30℃; for 24h; pH=8; Enzymatic reaction; stereoselective reaction; | 52% |
With lithium tri-t-butoxyaluminum hydride In tetrahydrofuran at 0℃; for 0.5h; | 0.695 g |
androst-4,9(11)-dien-3,17-dione
ethane-1,2-dithiol
4,9(11)-Androstadien-3,17-dion-3-ethylendithioacetal
Conditions | Yield |
---|---|
With boron trifluoride diethyl etherate In methanol for 0.25h; Ambient temperature; | 66% |
androst-4,9(11)-dien-3,17-dione
A
4,5α-9α,11-diepoxy-androstan-3,17-dione
B
9a,11-Epoxy-androst-4-ene-3,12,17-trione
Conditions | Yield |
---|---|
With C16H16F6FeN4O6S2; dihydrogen peroxide; acetic acid In acetonitrile at 20℃; for 0.5h; stereoselective reaction; | A 50% B 25% |
androst-4,9(11)-dien-3,17-dione
A
9α,11α-epoxy-4-androstene-3,17-dione
Conditions | Yield |
---|---|
With [Fe(tris(2-pyridyl)amine)(triflate)2]; dihydrogen peroxide In acetonitrile at 20℃; for 0.166667h; Catalytic behavior; stereoselective reaction; | A 28% B 20% |
androst-4,9(11)-dien-3,17-dione
A
9α,11α-epoxy-4-androstene-3,17-dione
B
4,5-epoxyandrost-9(11)-ene-3,17-dione
Conditions | Yield |
---|---|
With C16H16F6FeN4O6S2; dihydrogen peroxide; acetic acid In acetonitrile at 20℃; for 0.166667h; stereoselective reaction; | A 25% B 25% C 25% |
pyrrolidine
androst-4,9(11)-dien-3,17-dione
3-pyrrolidino-androsta-3,5,9(11)-trien-17-one
Conditions | Yield |
---|---|
With methanol |
androst-4,9(11)-dien-3,17-dione
N-bromoacetamide
9-bromo-11β-hydroxy-androst-4-ene-3,17-dione
androst-4,9(11)-dien-3,17-dione
potassium cyanide
17β-Cyano-17α-hydroxyandrosta-4,9(11)-dien-3-one
Conditions | Yield |
---|---|
With acetic acid In methanol at 25℃; |
androst-4,9(11)-dien-3,17-dione
potassium acetylide
A
17α-ethynyl-17β-hydroxy-4,9(11)-trieneandrostan-3-one
B
Pregna-4,9-dien-17α-ol-3-on-20-yne
Conditions | Yield |
---|---|
With acetylene In ethylenediamine at 20℃; for 2h; | A 0.03 g B 0.06 g |
androst-4,9(11)-dien-3,17-dione
(5α)-androst-9(11)-ene-3,17-dione
Conditions | Yield |
---|---|
With chromium(VI) oxide; lithium; ethylamine; tert-butyl alcohol 1.) THF, -70 deg C, 30 min, 2.) acetone; Multistep reaction; |
androst-4,9(11)-dien-3,17-dione
9-bromo-11β-hydroxy-androst-4-ene-3,17-dione
Conditions | Yield |
---|---|
With N-bromoacetamide |
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