3-oxoandrost-4-en-17α-yl benzoate
epitestosterone
Conditions | Yield |
---|---|
With potassium hydroxide In methanol at 65℃; for 4h; | 80% |
With potassium hydroxide |
17-epitestosterone 2-(prenyloxymethyl)benzoate
A
3,3-dimethyl acrylaldehyde
B
epitestosterone
C
17-methyl-18-norandrosta-4,13(17)-dien-3-one
Conditions | Yield |
---|---|
Stage #1: 17-epitestosterone 2-(prenyloxymethyl)benzoate With 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane; water at 20℃; for 6h; Stage #2: In dichloromethane at 20℃; for 24h; Further stages.; | A n/a B 30% C n/a D n/a |
Conditions | Yield |
---|---|
With sodium acetate at 60℃; Reduktion an Blei-Kathoden; |
Conditions | Yield |
---|---|
mit Hilfe von Actinomyces viridochromogenes; |
Androstene oxide
epitestosterone
Conditions | Yield |
---|---|
With manganese(IV) oxide; lithium aluminium tetrahydride |
Conditions | Yield |
---|---|
With potassium hydroxide In methanol Heating; Yield given; |
epitestosterone
Conditions | Yield |
---|---|
With potassium hydroxide |
epitestosterone
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: Yb(OTf)3*H2O / CH2Cl2 / 7 h / 20 °C 2.1: 85 percent / triphenylphosphine; diisopropyl azodicarboxylate / tetrahydrofuran / 1 h / 65 °C 3.1: DDQ / CH2Cl2; H2O / 6 h / 20 °C 3.2: 30 percent / Yb(ONf)3*xH2O / CH2Cl2 / 24 h / 20 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: 85 percent / triphenylphosphine; diisopropyl azodicarboxylate / tetrahydrofuran / 1 h / 65 °C 2.1: DDQ / CH2Cl2; H2O / 6 h / 20 °C 2.2: 30 percent / Yb(ONf)3*xH2O / CH2Cl2 / 24 h / 20 °C View Scheme |
testosterone 2-(prenyloxymethyl)benzoate
epitestosterone
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: DDQ / CH2Cl2; H2O / 6 h / 20 °C 2.1: Yb(OTf)3*H2O / CH2Cl2 / 7 h / 20 °C 3.1: 85 percent / triphenylphosphine; diisopropyl azodicarboxylate / tetrahydrofuran / 1 h / 65 °C 4.1: DDQ / CH2Cl2; H2O / 6 h / 20 °C 4.2: 30 percent / Yb(ONf)3*xH2O / CH2Cl2 / 24 h / 20 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 100 percent / pyridine / 0.25 h / 0 - 20 °C 2: 76 percent / 18-crown-6 / benzene / 72 h / Heating 3: 5percent KOH / methanol / Heating View Scheme | |
Multi-step reaction with 3 steps 1: 100 percent / pyridine / 0.25 h / 0 - 20 °C 2: 76 percent / CsOAc, 18-crow-6 / benzene / 72 h / Heating 3: 5percent KOH / methanol / Heating View Scheme |
Chloro-methanesulfonic acid (8R,9S,10R,13S,14S,17S)-10,13-dimethyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl ester
epitestosterone
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 76 percent / 18-crown-6 / benzene / 72 h / Heating 2: 5percent KOH / methanol / Heating View Scheme | |
Multi-step reaction with 2 steps 1: 76 percent / CsOAc, 18-crow-6 / benzene / 72 h / Heating 2: 5percent KOH / methanol / Heating View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: 44 percent / NaNO2 / dimethylsulfoxide / 1 h / 135 °C 2: 64 percent / pyridine / 20 h / Ambient temperature 3: 90 percent / conc. HCl / CHCl3; methanol / 64 h / Ambient temperature 4: 89 percent / aluminium isopropoxide / toluene; cyclohexanone / 0.75 h / Heating 5: 80 percent / 5percent KOH / methanol / 4 h / 65 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1: 99 percent / NaBH4 / methanol; ethyl acetate; CH2Cl2 / 1 h 2: pyridine / 72 h / 30 °C 3: 44 percent / NaNO2 / dimethylsulfoxide / 1 h / 135 °C 4: 64 percent / pyridine / 20 h / Ambient temperature 5: 90 percent / conc. HCl / CHCl3; methanol / 64 h / Ambient temperature 6: 89 percent / aluminium isopropoxide / toluene; cyclohexanone / 0.75 h / Heating 7: 80 percent / 5percent KOH / methanol / 4 h / 65 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: pyridine / 72 h / 30 °C 2: 44 percent / NaNO2 / dimethylsulfoxide / 1 h / 135 °C 3: 64 percent / pyridine / 20 h / Ambient temperature 4: 90 percent / conc. HCl / CHCl3; methanol / 64 h / Ambient temperature 5: 89 percent / aluminium isopropoxide / toluene; cyclohexanone / 0.75 h / Heating 6: 80 percent / 5percent KOH / methanol / 4 h / 65 °C View Scheme |
androst-5-ene-3β,17α-diyl 3-acetate 17-benzoate
epitestosterone
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 90 percent / conc. HCl / CHCl3; methanol / 64 h / Ambient temperature 2: 89 percent / aluminium isopropoxide / toluene; cyclohexanone / 0.75 h / Heating 3: 80 percent / 5percent KOH / methanol / 4 h / 65 °C View Scheme |
3β-hydroxyandrost-5-en-17α-yl benzoate
epitestosterone
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 89 percent / aluminium isopropoxide / toluene; cyclohexanone / 0.75 h / Heating 2: 80 percent / 5percent KOH / methanol / 4 h / 65 °C View Scheme |
17α-hydroxyandrost-5-en-3β-yl 3-acetate
epitestosterone
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 64 percent / pyridine / 20 h / Ambient temperature 2: 90 percent / conc. HCl / CHCl3; methanol / 64 h / Ambient temperature 3: 89 percent / aluminium isopropoxide / toluene; cyclohexanone / 0.75 h / Heating 4: 80 percent / 5percent KOH / methanol / 4 h / 65 °C View Scheme |
Conditions | Yield |
---|---|
With unidentified fungal species isolated from grinded corn In water at 37℃; for 1h; pH=7; aq. phosphate buffer; Microbiological reaction; Enzymatic reaction; |
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: unidentified fungal species isolated from grinded corn / water / 1 h / 37 °C / pH 7 / aq. phosphate buffer; Microbiological reaction; Enzymatic reaction 2: unidentified fungal species isolated from grinded corn / water / 1 h / 37 °C / pH 7 / aq. phosphate buffer; Microbiological reaction; Enzymatic reaction 3: unidentified fungal species isolated from grinded corn / water / 1 h / 37 °C / pH 7 / aq. phosphate buffer; Microbiological reaction; Enzymatic reaction View Scheme | |
Multi-step reaction with 4 steps 1: unidentified fungal species isolated from grinded corn / water / 1 h / 37 °C / pH 7 / aq. phosphate buffer; Microbiological reaction; Enzymatic reaction 2: unidentified fungal species isolated from grinded corn / water / 1 h / 37 °C / pH 7 / aq. phosphate buffer; Microbiological reaction; Enzymatic reaction 3: unidentified fungal species isolated from grinded corn / water / 1 h / 37 °C / pH 7 / aq. phosphate buffer; Microbiological reaction; Enzymatic reaction 4: unidentified fungal species isolated from grinded corn / water / 1 h / 37 °C / pH 7 / aq. phosphate buffer; Microbiological reaction; Enzymatic reaction View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: unidentified fungal species isolated from grinded corn / water / 1 h / 37 °C / pH 7 / aq. phosphate buffer; Microbiological reaction; Enzymatic reaction 2: unidentified fungal species isolated from grinded corn / water / 1 h / 37 °C / pH 7 / aq. phosphate buffer; Microbiological reaction; Enzymatic reaction View Scheme | |
Multi-step reaction with 3 steps 1: unidentified fungal species isolated from grinded corn / water / 1 h / 37 °C / pH 7 / aq. phosphate buffer; Microbiological reaction; Enzymatic reaction 2: unidentified fungal species isolated from grinded corn / water / 1 h / 37 °C / pH 7 / aq. phosphate buffer; Microbiological reaction; Enzymatic reaction 3: unidentified fungal species isolated from grinded corn / water / 1 h / 37 °C / pH 7 / aq. phosphate buffer; Microbiological reaction; Enzymatic reaction View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: unidentified fungal species isolated from grinded corn / water / 1 h / 37 °C / pH 7 / aq. phosphate buffer; Microbiological reaction; Enzymatic reaction 2: unidentified fungal species isolated from grinded corn / water / 1 h / 37 °C / pH 7 / aq. phosphate buffer; Microbiological reaction; Enzymatic reaction View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: unidentified fungal species isolated from grinded corn / water / 1 h / 37 °C / pH 7 / aq. phosphate buffer; Microbiological reaction; Enzymatic reaction 2: unidentified fungal species isolated from grinded corn / water / 1 h / 37 °C / pH 7 / aq. phosphate buffer; Microbiological reaction; Enzymatic reaction 3: unidentified fungal species isolated from grinded corn / water / 1 h / 37 °C / pH 7 / aq. phosphate buffer; Microbiological reaction; Enzymatic reaction View Scheme |
trimethylsilyl iodide
epitestosterone
Conditions | Yield |
---|---|
With 1,4-dithio-erythritol; N-methyl-N-trimethylsilyl-2,2,2-trifluoroacetamide at 60℃; for 0.25h; | 99% |
Conditions | Yield |
---|---|
In acetonitrile for 5h; Substitution; Heating; | 95% |
Conditions | Yield |
---|---|
With pyridine Ambient temperature; | 91% |
Conditions | Yield |
---|---|
With pyridine; acetic anhydride Ambient temperature; | 90% |
n-dodecanoyl chloride
epitestosterone
3-oxoandrost-4-en-17α-yl dodecanoate
Conditions | Yield |
---|---|
With pyridine Ambient temperature; | 89% |
epitestosterone
Conditions | Yield |
---|---|
With potassium dihydrogenphosphate; cytochrome P450 monooxygenase Lg-23 mutant at 25℃; for 20h; Enzymatic reaction; regioselective reaction; | 82% |
epitestosterone
tetradecanoyl chloride
3-oxoandrost-4-en-17α-yl tetradecanoate
Conditions | Yield |
---|---|
With pyridine Ambient temperature; | 80% |
Conditions | Yield |
---|---|
With di-isopropyl azodicarboxylate; triphenylphosphine In toluene at 80℃; for 1h; | 72% |
epitestosterone
Stearoyl chloride
3-oxoandrost-4-en-17α-yl octadecanoate
Conditions | Yield |
---|---|
With pyridine Ambient temperature; | 71% |
epitestosterone
A
5alpha-Androstane-17alpha-ol-3-one
B
5beta-Androstane-17alpha-ol-3-one
Conditions | Yield |
---|---|
With hydrogen; palladium on activated charcoal In ethanol | A 13% B 67% |
With hydrogen; Lindlar's catalyst In tetrahydrofuran for 2h; | A 11% B 66% |
With hydrogen; palladium on activated charcoal In methanol | A 22 % Chromat. B 76 % Chromat. |
Conditions | Yield |
---|---|
With pyridine Ambient temperature; | 62% |
Conditions | Yield |
---|---|
With pyridine Ambient temperature; | 57% |
Conditions | Yield |
---|---|
With pyridine for 6h; Ambient temperature; | 55% |
epitestosterone
(trifluoromethyl)trimethylsilane
Conditions | Yield |
---|---|
With potassium fluoride; 2-fluoropyridine; silver trifluoromethanesulfonate; Selectfluor In ethyl acetate at 20℃; for 12h; Glovebox; Inert atmosphere; | 54% |
epitestosterone
Heptanoic acid chloride
3-oxoandrost-4-en-17α-yl heptanoate
Conditions | Yield |
---|---|
With pyridine Ambient temperature; | 53% |
Conditions | Yield |
---|---|
With pyridine at 20℃; | 41% |
Conditions | Yield |
---|---|
With sodium In pentan-1-ol for 0.666667h; Heating; | 7% |
Multi-step reaction with 2 steps 1: 13 percent / hydrogen / 10percent Pd/C / ethanol 2: 20 percent / hydrogen / platinum / acetic acid View Scheme |
epitestosterone
p-toluenesulfonyl chloride
17α-(toluene-4-sulfonyloxy)-androst-4-en-3-one
Conditions | Yield |
---|---|
In tetrahydrofuran |
epitestosterone
Conditions | Yield |
---|---|
With N-(2-chloro-1,1,2-trifluoroethyl)diethylamine In tetrahydrofuran | |
Multi-step reaction with 2 steps 1: pyridine / 0 °C 2: Zn(OAc)2 / dioxane / 8 h / 90 °C View Scheme | |
Multi-step reaction with 2 steps 1: pyridine / 0 °C 2: Zn(OAc)2 / dioxane / 24 h / 90 °C View Scheme |
epitestosterone
Conditions | Yield |
---|---|
With N-(2-chloro-1,1,2-trifluoroethyl)diethylamine In tetrahydrofuran |
Conditions | Yield |
---|---|
reaction with green cell suspension culture of Marchantia polymorpha; |
Conditions | Yield |
---|---|
With propylene glycol; human adrenal hydroxysteroid sulfotransferase (EC 2.8.2.2); PAPS for 0.166667h; Kinetics; |
epitestosterone
tert-butyldimethylsilyl chloride
(8R,9S,10R,13S,14S,17R)-17-(tert-Butyl-dimethyl-silanyloxy)-10,13-dimethyl-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-3-one
Conditions | Yield |
---|---|
With 1H-imidazole In N,N-dimethyl-formamide Ambient temperature; |
epitestosterone
Conditions | Yield |
---|---|
With potassium tert-butylate; tert-butyl alcohol |
Molecular Structure of Epitestosterone (CAS NO.481-30-1):
Molecular Formula: C19H28O2
Molecular Weight: 288.4244
IUPAC Name: (8R,9S,10R,13S,14S,17R)-17-Hydroxy-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
Synonyms of Epitestosterone (CAS NO.481-30-1): (17-alpha)-17-Hydroxyandrost-4-en-3-one ; 17-Epitestosterone ; 17-alpha-Hydroxyandrost-4-en-3-one ; 17-alpha-Testosterone ; 17alpha-Hydroxyandrost-4-en-3-one ; 17alpha-Testosterone ; BRN 1915396 ; Isotestosterone ; NSC 26499 ; cis-Testosterone ; Androst-4-en-3-one, 17-alpha-hydroxy- ; Androst-4-en-3-one, 17-hydroxy-, (17-alpha)- (9CI) ; Androst-4-en-3-one, 17-hydroxy-, (17alpha)- ; Androst-4-en-3-one, 17alpha-hydroxy- (8CI)
CAS NO: 481-30-1
Classification Code: Hormone ; Reproductive Effect
Polar Surface Area: 26.3 Å2
Index of Refraction: 1.56
Molar Refractivity: 83.11 cm3
Molar Volume: 256.9 cm3
Surface Tension: 44.4 dyne/cm
Density of Epitestosterone (CAS NO.481-30-1): 1.12 g/cm3
Flash Point: 184.7 °C
Enthalpy of Vaporization: 79.52 kJ/mol
Boiling Point: 432.9 °C at 760 mmHg
Vapour Pressure: 2.6E-09 mmHg at 25°C
Hazard Codes of Epitestosterone (CAS NO.481-30-1): Xn
Risk Statements: 68
R68: Possible risk of irreversible effects.
Safety Statements: 22-36
S22: Do not breathe dust.
S36: Wear suitable protective clothing.
WGK Germany: 3
RTECS: BV8395600
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