Conditions | Yield |
---|---|
With pyridine; dmap at 20℃; for 24h; Inert atmosphere; | 100% |
With pyridine at 0 - 20℃; | 99% |
With copper(II) bis(trifluoromethanesulfonate) In dichloromethane at 20℃; for 3h; | 92% |
Conditions | Yield |
---|---|
With potassium fluoride on basic alumina In toluene for 2.5h; | 98% |
With pyridine; acetic anhydride for 4h; Reflux; | 96% |
With immobilized p-toluenesulfonic acid polymer bound macroporous In neat (no solvent) at 100℃; for 0.0416667h; Microwave irradiation; Sealed tube; Green chemistry; | 33% |
With pyridine; acetic anhydride for 4h; Reflux; |
Conditions | Yield |
---|---|
With palladium 10% on activated carbon; ammonium formate In ethanol at 75 - 77℃; for 9.5h; Inert atmosphere; | 97.6% |
A
testosterone acetate
Conditions | Yield |
---|---|
With 3,3-dimethyldioxirane In acetone at 20℃; for 1h; Yields of byproduct given; | A 95% B n/a |
Conditions | Yield |
---|---|
With Amberlyst 15; sodium iodide In acetone at 20℃; for 6h; deoxygenation; | 95% |
Conditions | Yield |
---|---|
Stage #1: acetic acid With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In chloroform at 20℃; for 0.5h; Inert atmosphere; Stage #2: testosterone With dmap In chloroform for 18h; Inert atmosphere; Reflux; | 95% |
Conditions | Yield |
---|---|
With C12F18O13Zn4 for 40h; Reflux; Inert atmosphere; | 93% |
Conditions | Yield |
---|---|
With tert.-butylhydroperoxide; cobalt(II) acetate In decane; acetonitrile at 55℃; for 3h; | 70% |
acetic anhydride
17β-<(t-butyldimethylsilyl)oxy>androst-4-en-3-one
testosterone acetate
Conditions | Yield |
---|---|
copper(II) bis(trifluoromethanesulfonate) In dichloromethane at 20℃; for 24h; | 67% |
Acetic acid (2S,8R,9S,10R,13S,14S,17S)-4-bromo-10,13-dimethyl-2-morpholin-4-yl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl ester
A
testosterone acetate
B
17β-acetoxy-4-bromo-4-androsten-3-one
Conditions | Yield |
---|---|
With zinc In acetic acid at 25℃; for 15h; | A 30% B 64% |
testosterone
acetic acid
A
di(4-methyl)phenylthiosulfonate
B
testosterone acetate
C
(9S,10R,13S,14S)-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 4-methylbenzenesulfinate
Conditions | Yield |
---|---|
With p-toluene sulfinic acid In dichloromethane for 24h; Ambient temperature; | A 20 mg B 60% C 10 mg |
A
testosterone acetate
B
17β-acetoxy-4,5-secoandrostane-3,5-dione
Conditions | Yield |
---|---|
With zinc In acetic acid for 12h; Heating; Yields of byproduct given; | A 44% B n/a |
With zinc In acetic acid for 12h; Heating; Yield given; | A 44% B n/a |
Conditions | Yield |
---|---|
With thallium(III) nitrate trihydrate In diethylene glycol dimethyl ether for 24h; Ambient temperature; | 34% |
17β-acetoxy-3-ethoxy-androsta-3,5-diene
testosterone acetate
Conditions | Yield |
---|---|
With hydrogenchloride; acetone | |
With hydrogenchloride; acetone |
17β-acetoxy-3β-formyloxy-androst-5-ene
testosterone acetate
testosterone acetate
3β.3'β-dihydroxy-17β.17β'-diacetoxy-[3.3']bi[androsten-(4)-yl]
testosterone acetate
Conditions | Yield |
---|---|
With chloroform; bromine Behandeln des Reaktionsprodukts mit CrO3 in wasserhaltiger Essigsaeure und Aether und Schuetteln des danach erhaltenen Reaktionsprodukts mit Zink-Pulver und wss.Essigsaeure; |
Conditions | Yield |
---|---|
With acetic acid at 180℃; |
Conditions | Yield |
---|---|
With aluminum tri-tert-butoxide; acetone; toluene | |
With bromine; acetic acid nachfolgendes Erwaermen mit CrO3 in Essigsaeure und Erwaermen des Reaktionsprodukts mit Zink-Pulver und Essigsaeure; | |
With bromine; acetic acid nachfolgendes Erwaermen mit CrO3 in Essigsaeure und Erwaermen des Reaktionsprodukts mit NaI in Aethanol; |
17-chloroandrost-4-en-3-one
potassium acetate
acetic acid
testosterone acetate
Conditions | Yield |
---|---|
at 150 - 180℃; |
androstenediol-17-acetate
aluminum tri-tert-butoxide
acetone
toluene
testosterone acetate
androstenediol-17-acetate
aluminum tri-tert-butoxide
acetone
benzene
testosterone acetate
Conditions | Yield |
---|---|
With potassium phosphate; 1,2-dilauroylphosphatidylcholine; NADPH; magnesium chloride Mechanism; microsomes from pig tests, CYP-17, cytochrome P450 reductase; |
17β-acetoxy-4-oxa-androst-5-en-3-one
acetic acid
dimethyl methane phosphonate
A
testosterone
B
testosterone acetate
Conditions | Yield |
---|---|
Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts; |
17β-acetoxy-4-oxa-androst-5-en-3-one
dimethyl methane phosphonate
A
testosterone
B
testosterone acetate
Conditions | Yield |
---|---|
Yield given. Multistep reaction. Yields of byproduct given; |
Progesterone
A
testosterone acetate
B
6β,11α-dihydroxyprogesterone
C
12β,17α-dihydroxyprogesterone
Conditions | Yield |
---|---|
With Cephalosporium aphidicola In ethanol for 168h; | A 33 mg B 1.1 g C 39 mg D 41 mg |
Progesterone
A
testosterone
B
pregna-1,4-diene-3,20-dione
C
Androstenedione
D
testosterone acetate
E
11-alpha-hydroxyprogesterone
F
1-dehydrotestosterone
Conditions | Yield |
---|---|
With immobilized spores of Aspergillus ochraceus; Tris-maleate buffer at 30℃; for 48h; Product distribution; Mechanism; various water activity of the biocatalysts; |
17β-acetoxy-3α,4α-epoxy-5α-hydroxyandrostane
A
testosterone acetate
B
17β-acetoxy-4-methylestra-1,3,5(10)-triene
C
17β-acetyloxy-5α-androst-2-en-4-one
Conditions | Yield |
---|---|
With hydrogen bromide; acetic acid for 0.25h; Rearrangement; Heating; | A 15 mg B 29 mg C 10 mg |
Conditions | Yield |
---|---|
With sodium tetrahydroborate; acetic acid; trifluoroacetic acid In dichloromethane; acetonitrile at 20℃; for 3.5h; Inert atmosphere; | 99% |
With sodium tetrahydroborate; acetic acid; trifluoroacetic acid In dichloromethane; acetonitrile at 0℃; for 10h; | 80% |
(i) EtSH, HCl, Et2O, (ii) Raney-Ni, dioxane; Multistep reaction; | |
With sodium tetrahydroborate; acetic acid; trifluoroacetic acid In dichloromethane; acetonitrile for 1h; Ambient temperature; | 2.2 g |
testosterone acetate
(3β,17β)-3-hydroxyandrost-4-en-17-yl acetate
Conditions | Yield |
---|---|
With methanol; sodium tetrahydroborate In tetrahydrofuran at 0℃; | 97.3% |
With sodium tetrahydroborate In methanol at 0℃; for 2h; | 74% |
With sodium tetrahydroborate In methanol at 0℃; for 2h; | |
With lithium tri-(tert-butoxy)aluminum hydride In tetrahydrofuran for 3.5h; Inert atmosphere; Reflux; |
Conditions | Yield |
---|---|
With hydrogen; palladium In pyridine for 16h; | 97% |
Multi-step reaction with 2 steps 1: H2 / PtO2 / acetic acid / 1 h / Ambient temperature 2: Jones reagent / acetone / 0.08 h View Scheme |
testosterone acetate
17β-acetoxy-4-bromo-4-androsten-3-one
Conditions | Yield |
---|---|
Stage #1: testosterone acetate With 3,3-dimethyldioxirane In acetone at 20℃; for 8h; Epoxidation; Stage #2: With Amberlyst 15; sodium bromide In acetone at 20℃; for 12h; Bromination; | 97% |
Conditions | Yield |
---|---|
With copper dichloride In methanol; water for 20h; Heating; | 95% |
With bis(tri-n-butyltin)oxide In toluene at 110℃; for 27h; | 59% |
With potassium hydroxide |
pyrrolidine
testosterone acetate
3-(1-pyrrolidinyl)-17β-acetoxyandrosta-3,5-diene
Conditions | Yield |
---|---|
92% | |
In methanol Heating; | 84% |
Conditions | Yield |
---|---|
Stage #1: testosterone acetate With 3,3-dimethyldioxirane In acetone at 20℃; for 8h; Epoxidation; Stage #2: With Amberlyst 15; sodium chloride In acetone at 20℃; for 12h; Chlorination; | 89% |
With pyridine; sulfuryl dichloride for 1h; Product distribution; Ambient temperature; other steroids; | |
With pyridine; sulfuryl dichloride for 1h; Ambient temperature; | |
Multi-step reaction with 2 steps 1: N-chloro-succinimide, HN3 / CHCl3; 2-methyl-propan-2-ol 2: SiO2 / benzene View Scheme | |
Multi-step reaction with 2 steps 1: N-chloro-succinimide, HN3 / CHCl3; 2-methyl-propan-2-ol 2: SiO2 / benzene View Scheme |
testosterone acetate
3-((3S,3aS,5aS,6R,9aS,9bS)-3-acetoxy-3a,6-dimethyl-7-oxododecahydro-1H-cyclopenta[a]naphthalen-6-yl)propanoic acid
Conditions | Yield |
---|---|
With potassium permanganate; sodium periodate; sodium carbonate In water; tert-butyl alcohol at 70℃; for 0.333333h; Inert atmosphere; | 88% |
With potassium permanganate; potassium metaperiodate; potassium carbonate In water; tert-butyl alcohol for 2h; | 76% |
With potassium permanganate; sodium periodate; sodium carbonate In water; isopropyl alcohol for 1h; Heating; |
testosterone acetate
Acetic acid (8R,9S,10R,13S,14S,17S)-10,13-dimethyl-3-[(2-phenyl-quinoline-5-carbonyl)-hydrazono]-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl ester
Conditions | Yield |
---|---|
With pyridine In ethanol for 40h; Heating; | 87% |
isoniazid
testosterone acetate
Acetic acid (8R,9S,10R,13S,14S,17S)-10,13-dimethyl-3-[(pyridine-4-carbonyl)-hydrazono]-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl ester
Conditions | Yield |
---|---|
With pyridine In ethanol for 25h; Heating; | 86% |
testosterone acetate
ethylenediamine
17β-acetoxy-4'-dehydro-androst-4-eno[3,4-e]piperazin-6-one
Conditions | Yield |
---|---|
With aluminum oxide at 120℃; microwave irradiation; | 85% |
testosterone acetate
Δ4-Androsten-2,17-diol-3-on-diacetat
Conditions | Yield |
---|---|
In benzene at 80℃; for 25h; | 83% |
testosterone acetate
Nα-<1,2-bis(p-methoxyphenyl)butyl>-α-aminoacetohydrazide
Acetic acid (8R,9S,10R,13S,14S,17S)-3-({2-[1,2-bis-(4-methoxy-phenyl)-butylamino]-acetyl}-hydrazono)-10,13-dimethyl-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl ester
Conditions | Yield |
---|---|
With acetic acid In ethanol Heating; | 80% |
Conditions | Yield |
---|---|
In tetrahydrofuran; diethyl ether Grignard reaction; | 76% |
morpholine
testosterone acetate
3-morpholinoandrosta-2,5-dein-17β-yl acetate
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In toluene for 16h; Heating; | 75% |
methanol
testosterone acetate
A-nor-2α-methoxycarbonyl-3-androsten-17β-yl acetate
Conditions | Yield |
---|---|
With thallium(III) nitrate; trimethyl orthoformate for 0.5h; | 75% |
testosterone acetate
trimethyl orthoformate
A-nor-2α-methoxycarbonyl-3-androsten-17β-yl acetate
Conditions | Yield |
---|---|
With thallium(III) nitrate In methanol at 0℃; for 0.5h; | 75% |
testosterone acetate
17β-acetoxy-3-hydroximinoandrost-4-ene
Conditions | Yield |
---|---|
With pyridine; hydroxylamine hydrochloride for 6h; Reflux; | 74% |
Conditions | Yield |
---|---|
With potassium hydroxide; sodium hydrogencarbonate; acetic acid In 1,2-dimethoxyethane for 15h; Ambient temperature; | 70% |
testosterone acetate
4-aminobenzohydrazide
Acetic acid (8R,9S,10R,13S,14S,17S)-3-[(4-amino-benzoyl)-hydrazono]-10,13-dimethyl-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl ester
Conditions | Yield |
---|---|
With pyridine In ethanol for 25h; Heating; | 70% |
Conditions | Yield |
---|---|
With potato dextrose broth medium In ethanol at 24 - 26℃; for 96h; Penicillium decumbens ATCC 10436; | 68% |
Multi-step reaction with 2 steps 1: H2 / PtO2 / acetic acid / 1 h / Ambient temperature 2: Jones reagent / acetone / 0.08 h View Scheme |
testosterone acetate
17beta-Acetoxyandrost-4-ene-3,6-dione
Conditions | Yield |
---|---|
With tert.-butylhydroperoxide; Rh2(cap)4 In water at 40℃; for 16h; Product distribution / selectivity; Allylic oxidation; | 68% |
With tert.-butylhydroperoxide; [Rh2(cap)4*2CH3CN] In water at 40℃; for 48h; | 68% |
With tert.-butylhydroperoxide; Rh2(cap)4 In 1,2-dichloro-ethane at 40℃; for 16h; Product distribution / selectivity; Allylic oxidation; | 50% |
With tert.-butylhydroperoxide; Clorox bleach | |
Multi-step reaction with 2 steps 1: TsOH / dioxane 2: (tBuO)2CrO2 / CCl4 View Scheme |
The Testosterone acetate is an organic compound with the formula C21H30O3. The IUPAC name of this chemical is [(8R,9S,10R,13S,14S,17S)-10,13-dimethyl-3-oxo-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl] acetate. With the CAS registry number 1045-69-8, it is also named as (17β)-3-Oxoandrost-4-en-17-yl acetate. The product's category is Steroids.
Physical properties about Testosterone acetate are: (1)ACD/LogP: 4.14; (2)ACD/LogD (pH 5.5): 4.144; (3)ACD/LogD (pH 7.4): 4.144; (4)ACD/BCF (pH 5.5): 831.141; (5)ACD/BCF (pH 7.4): 831.141; (6)ACD/KOC (pH 5.5): 4280.594; (7)ACD/KOC (pH 7.4): 4280.594; (8)#H bond acceptors: 3; (9)#Freely Rotating Bonds: 2; (10)Polar Surface Area: 43.37 Å2; (11)Index of Refraction: 1.541; (12)Molar Refractivity: 92.697 cm3; (13)Molar Volume: 295.028 cm3; (14)Polarizability: 36.748×10-24cm3; (15)Surface Tension: 42.273 dyne/cm; (16)Density: 1.12 g/cm3; (17)Flash Point: 191.472 °C; (18)Enthalpy of Vaporization: 69.917 kJ/mol; (19)Boiling Point: 441.803 °C at 760 mmHg.
When you are using this chemical, please be cautious about it as the following:
It is harmful if swallowed and may cause cancer. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. Besides, this chemical is Possible risk of harm to the unborn child. When you are using it, wear suitable protective clothing, do not breathe dust and avoid exposure - obtain special instructions before use.
You can still convert the following datas into molecular structure:
(1)SMILES: CC(=O)O[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CCC4=CC(=O)CC[C@]34C)C
(2)InChI: InChI=1/C21H30O3/c1-13(22)24-19-7-6-17-16-5-4-14-12-15(23)8-10-20(14,2)18(16)9-11-21(17,19)3/h12,16-19H,4-11H2,1-3H3/t16-,17-,18-,19-,20-,21-/m0/s1
(3)InChIKey: DJPZSBANTAQNFN-PXQJOHHUBX
(4)Std. InChI: InChI=1S/C21H30O3/c1-13(22)24-19-7-6-17-16-5-4-14-12-15(23)8-10-20(14,2)18(16)9-11-21(17,19)3/h12,16-19H,4-11H2,1-3H3/t16-,17-,18-,19-,20-,21-/m0/s1
(5)Std. InChIKey: DJPZSBANTAQNFN-PXQJOHHUSA-N
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