3-Aethylendioxy-1-methylen-5α-androstanol-(17β)
17β-hydroxy-1-methyl-5α-androst-1-en-3-one
Conditions | Yield |
---|---|
(i) Zn-Cu, I2, CH2I2, Et2O, (ii) aq. H2SO4, MeOH; Multistep reaction; |
A
17β-hydroxy-1-methyl-5α-androst-1-en-3-one
F
1-methyl-5α-androst-1-ene-3,17-dione
Conditions | Yield |
---|---|
With Aspergillus niger In methanol at 26℃; for 288h; Microbiological reaction; |
17β-hydroxy-1-methyl-5α-androst-1-en-3-one
Conditions | Yield |
---|---|
With Cunninghamella blakesleeana In methanol at 26℃; for 288h; Microbiological reaction; |
17β-hydroxy-1-methyl-5α-androst-1-en-3-one
tert-butyldimethylsilyl chloride
17β-(tert.-butyldimethylsilyloxy)-1-methyl-5α-androsta-1-en-3-one
Conditions | Yield |
---|---|
With 1H-imidazole In N,N-dimethyl-formamide for 24h; Ambient temperature; | 96% |
17β-hydroxy-1-methyl-5α-androst-1-en-3-one
atamestane
Conditions | Yield |
---|---|
With diphenyl diselenide; iodosylbenzene In toluene at 80℃; for 9h; | 51% |
Conditions | Yield |
---|---|
With liver microsomes from Aroclor 1254-induced male Wistar rat In methanol; phosphate buffer at 37℃; pH=7.4; | A 24% B 28% |
17β-hydroxy-1-methyl-5α-androst-1-en-3-one
A
1β-Methyl-4,5α-dihydro-testosteron (17β-Hydroxy-1β-methyl-5α-androstan-3-on)
B
mesterolone
Conditions | Yield |
---|---|
With 2,2'-azobis(isobutyronitrile); tributylzinc hydride In tetrahydrofuran for 1h; Heating; Yield given. Yields of byproduct given; |
17β-hydroxy-1-methyl-5α-androst-1-en-3-one
(1S,5R,8R,9S,10S,13S,14S,17S)-1,10,13-Trimethyl-17-trimethylsilanyloxy-hexadecahydro-cyclopenta[a]phenanthren-3-one
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: Tributylzinnhydrid, Azobisisobutyronitril / tetrahydrofuran / 1 h / Heating 2: hexamethyldisilazane / pyridine / 0.25 h View Scheme |
17β-hydroxy-1-methyl-5α-androst-1-en-3-one
(1S,5S,8R,9S,10S,13S,14S,17S)-1,10,13-Trimethyl-17-trimethylsilanyloxy-hexadecahydro-cyclopenta[a]phenanthren-3-one
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: Tributylzinnhydrid, Azobisisobutyronitril / tetrahydrofuran / 1 h / Heating 2: hexamethyldisilazane / pyridine / 0.25 h View Scheme |
17β-hydroxy-1-methyl-5α-androst-1-en-3-one
1,4-dimethylandrosta-1,4-dien-3,17-dione
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1: 96 percent / imidazole / dimethylformamide / 24 h / Ambient temperature 2: 1.) lithium diisopropylamide / 1.) THF, 0 deg, 15 min; 2.) THF, -78 deg C, 3 h; 3.) THF, -78 deg C, 15 min; 4.) r.t., 30 min 3: 87 percent / acetic acid / tetrahydrofuran; H2O / 72 h / 50 - 60 °C 4: 95 percent / dimethylaminopyridine / pyridine / 4 h / Ambient temperature 5: 31 percent / iodoxybenzene, diphenyl diselenide / toluene / 7 h / 80 °C 6: 92 percent / 3 percent potassium hydroxide / methanol / 4 h / Ambient temperature 7: 83 percent / chromium trioxide, conc. sulfuric acid / H2O; acetone / 0.25 h / Ambient temperature View Scheme |
17β-hydroxy-1-methyl-5α-androst-1-en-3-one
17β-hydroxy-1,4α-dimethyl-5α-androst-1-en-3-one
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 96 percent / imidazole / dimethylformamide / 24 h / Ambient temperature 2: 1.) lithium diisopropylamide / 1.) THF, 0 deg, 15 min; 2.) THF, -78 deg C, 3 h; 3.) THF, -78 deg C, 15 min; 4.) r.t., 30 min 3: 87 percent / acetic acid / tetrahydrofuran; H2O / 72 h / 50 - 60 °C View Scheme |
17β-hydroxy-1-methyl-5α-androst-1-en-3-one
1,4α-dimethyl-5α-androst-1-en-3,17-dione
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 96 percent / imidazole / dimethylformamide / 24 h / Ambient temperature 2: 1.) lithium diisopropylamide / 1.) THF, 0 deg, 15 min; 2.) THF, -78 deg C, 3 h; 3.) THF, -78 deg C, 15 min; 4.) r.t., 30 min 3: 87 percent / acetic acid / tetrahydrofuran; H2O / 72 h / 50 - 60 °C 4: 84 percent / chromium trioxide, conc. sulfuric acid / H2O; acetone / 0.25 h / Ambient temperature View Scheme |
17β-hydroxy-1-methyl-5α-androst-1-en-3-one
17β-hydroxy-1,2,4α-trimethyl-5α-androst-1-en-3-one
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1: 96 percent / imidazole / dimethylformamide / 24 h / Ambient temperature 2: 1.) lithium diisopropylamide / 1.) THF, 0 deg, 15 min; 2.) THF, -78 deg C, 3 h; 3.) THF, -78 deg C, 15 min; 4.) r.t., 30 min 3: 87 percent / acetic acid / tetrahydrofuran; H2O / 72 h / 50 - 60 °C 4: 95 percent / dimethylaminopyridine / pyridine / 4 h / Ambient temperature 5: 42 percent / various solvent(s); H2O; ethanol / 80 h / 110 °C 6: 70 percent / Raney nickel / acetone / 0.25 h / Heating 7: 90 percent / 3 percent potassium hydroxide / methanol / 4 h / Ambient temperature; 2 View Scheme |
17β-hydroxy-1-methyl-5α-androst-1-en-3-one
17β-hydroxy-1,4-dimethylandrosta-1,4-dien-3-one
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: 96 percent / imidazole / dimethylformamide / 24 h / Ambient temperature 2: 1.) lithium diisopropylamide / 1.) THF, 0 deg, 15 min; 2.) THF, -78 deg C, 3 h; 3.) THF, -78 deg C, 15 min; 4.) r.t., 30 min 3: 87 percent / acetic acid / tetrahydrofuran; H2O / 72 h / 50 - 60 °C 4: 95 percent / dimethylaminopyridine / pyridine / 4 h / Ambient temperature 5: 31 percent / iodoxybenzene, diphenyl diselenide / toluene / 7 h / 80 °C 6: 92 percent / 3 percent potassium hydroxide / methanol / 4 h / Ambient temperature View Scheme |
17β-hydroxy-1-methyl-5α-androst-1-en-3-one
1,2,4α-trimethyl-5α-androst-1-en-3,17-dione
Conditions | Yield |
---|---|
Multi-step reaction with 8 steps 1: 96 percent / imidazole / dimethylformamide / 24 h / Ambient temperature 2: 1.) lithium diisopropylamide / 1.) THF, 0 deg, 15 min; 2.) THF, -78 deg C, 3 h; 3.) THF, -78 deg C, 15 min; 4.) r.t., 30 min 3: 87 percent / acetic acid / tetrahydrofuran; H2O / 72 h / 50 - 60 °C 4: 95 percent / dimethylaminopyridine / pyridine / 4 h / Ambient temperature 5: 42 percent / various solvent(s); H2O; ethanol / 80 h / 110 °C 6: 70 percent / Raney nickel / acetone / 0.25 h / Heating 7: 90 percent / 3 percent potassium hydroxide / methanol / 4 h / Ambient temperature; 2 8: 83 percent / chromium trioxide, conc. sulfuric acid / H2O; acetone / 0.25 h / Ambient temperature View Scheme |
17β-hydroxy-1-methyl-5α-androst-1-en-3-one
17β-hydroxy-1,2,4-trimethylandrosta-1,4-dien-3-one
Conditions | Yield |
---|---|
Multi-step reaction with 8 steps 1: 96 percent / imidazole / dimethylformamide / 24 h / Ambient temperature 2: 1.) lithium diisopropylamide / 1.) THF, 0 deg, 15 min; 2.) THF, -78 deg C, 3 h; 3.) THF, -78 deg C, 15 min; 4.) r.t., 30 min 3: 87 percent / acetic acid / tetrahydrofuran; H2O / 72 h / 50 - 60 °C 4: 95 percent / dimethylaminopyridine / pyridine / 4 h / Ambient temperature 5: 42 percent / various solvent(s); H2O; ethanol / 80 h / 110 °C 6: 70 percent / Raney nickel / acetone / 0.25 h / Heating 7: 33 percent / iodoxybenzene, diphenyl diselenide / toluene / 80 °C 8: 90 percent / 3 percent potassium hydroxide / methanol / 4 h / Ambient temperature View Scheme |
17β-hydroxy-1-methyl-5α-androst-1-en-3-one
1,2,4-trimethylandrosta-1,4-dien-3,17-dione
Conditions | Yield |
---|---|
Multi-step reaction with 9 steps 1: 96 percent / imidazole / dimethylformamide / 24 h / Ambient temperature 2: 1.) lithium diisopropylamide / 1.) THF, 0 deg, 15 min; 2.) THF, -78 deg C, 3 h; 3.) THF, -78 deg C, 15 min; 4.) r.t., 30 min 3: 87 percent / acetic acid / tetrahydrofuran; H2O / 72 h / 50 - 60 °C 4: 95 percent / dimethylaminopyridine / pyridine / 4 h / Ambient temperature 5: 42 percent / various solvent(s); H2O; ethanol / 80 h / 110 °C 6: 70 percent / Raney nickel / acetone / 0.25 h / Heating 7: 33 percent / iodoxybenzene, diphenyl diselenide / toluene / 80 °C 8: 90 percent / 3 percent potassium hydroxide / methanol / 4 h / Ambient temperature 9: 82 percent / chromium trioxide, conc. sulfuric acid / H2O; acetone / 0.25 h / Ambient temperature View Scheme |
17β-hydroxy-1-methyl-5α-androst-1-en-3-one
17β-acetyloxy-1,4α-dimethyl-5α-androst-1-en-3-one
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 96 percent / imidazole / dimethylformamide / 24 h / Ambient temperature 2: 1.) lithium diisopropylamide / 1.) THF, 0 deg, 15 min; 2.) THF, -78 deg C, 3 h; 3.) THF, -78 deg C, 15 min; 4.) r.t., 30 min 3: 87 percent / acetic acid / tetrahydrofuran; H2O / 72 h / 50 - 60 °C 4: 95 percent / dimethylaminopyridine / pyridine / 4 h / Ambient temperature View Scheme |
17β-hydroxy-1-methyl-5α-androst-1-en-3-one
17β-acetyloxy-1,2,4α-trimethyl-5α-androst-1-en-3-one
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: 96 percent / imidazole / dimethylformamide / 24 h / Ambient temperature 2: 1.) lithium diisopropylamide / 1.) THF, 0 deg, 15 min; 2.) THF, -78 deg C, 3 h; 3.) THF, -78 deg C, 15 min; 4.) r.t., 30 min 3: 87 percent / acetic acid / tetrahydrofuran; H2O / 72 h / 50 - 60 °C 4: 95 percent / dimethylaminopyridine / pyridine / 4 h / Ambient temperature 5: 42 percent / various solvent(s); H2O; ethanol / 80 h / 110 °C 6: 70 percent / Raney nickel / acetone / 0.25 h / Heating View Scheme |
17β-hydroxy-1-methyl-5α-androst-1-en-3-one
17β-acetyloxy-1,4-dimethylandrosta-1,4-dien-3-one
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: 96 percent / imidazole / dimethylformamide / 24 h / Ambient temperature 2: 1.) lithium diisopropylamide / 1.) THF, 0 deg, 15 min; 2.) THF, -78 deg C, 3 h; 3.) THF, -78 deg C, 15 min; 4.) r.t., 30 min 3: 87 percent / acetic acid / tetrahydrofuran; H2O / 72 h / 50 - 60 °C 4: 95 percent / dimethylaminopyridine / pyridine / 4 h / Ambient temperature 5: 31 percent / iodoxybenzene, diphenyl diselenide / toluene / 7 h / 80 °C View Scheme |
17β-hydroxy-1-methyl-5α-androst-1-en-3-one
17β-acetyloxy-1,2,4-trimethylandrosta-1,4-dien-3-one
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1: 96 percent / imidazole / dimethylformamide / 24 h / Ambient temperature 2: 1.) lithium diisopropylamide / 1.) THF, 0 deg, 15 min; 2.) THF, -78 deg C, 3 h; 3.) THF, -78 deg C, 15 min; 4.) r.t., 30 min 3: 87 percent / acetic acid / tetrahydrofuran; H2O / 72 h / 50 - 60 °C 4: 95 percent / dimethylaminopyridine / pyridine / 4 h / Ambient temperature 5: 42 percent / various solvent(s); H2O; ethanol / 80 h / 110 °C 6: 70 percent / Raney nickel / acetone / 0.25 h / Heating 7: 33 percent / iodoxybenzene, diphenyl diselenide / toluene / 80 °C View Scheme |
17β-hydroxy-1-methyl-5α-androst-1-en-3-one
17β-(tert.-butyldimethylsilyloxy)-1,4α-dimethyl-5α-androsta-1-en-3-one
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 96 percent / imidazole / dimethylformamide / 24 h / Ambient temperature 2: 1.) lithium diisopropylamide / 1.) THF, 0 deg, 15 min; 2.) THF, -78 deg C, 3 h; 3.) THF, -78 deg C, 15 min; 4.) r.t., 30 min View Scheme |
17β-hydroxy-1-methyl-5α-androst-1-en-3-one
17β-acetyloxy-1,4α-dimethyl-2-<(phenylthio)methyl>-5α-androst-1-en-3-one
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: 96 percent / imidazole / dimethylformamide / 24 h / Ambient temperature 2: 1.) lithium diisopropylamide / 1.) THF, 0 deg, 15 min; 2.) THF, -78 deg C, 3 h; 3.) THF, -78 deg C, 15 min; 4.) r.t., 30 min 3: 87 percent / acetic acid / tetrahydrofuran; H2O / 72 h / 50 - 60 °C 4: 95 percent / dimethylaminopyridine / pyridine / 4 h / Ambient temperature 5: 42 percent / various solvent(s); H2O; ethanol / 80 h / 110 °C View Scheme |
N-methyl-N-trimethylsilyl-2,2,2-trifluoroacetamide
17β-hydroxy-1-methyl-5α-androst-1-en-3-one
C26H46O2Si2
Conditions | Yield |
---|---|
With ammonium iodide; 2-hydroxyethanethiol at 60℃; for 0.333333h; | |
With ammonium iodide; ethanethiol In acetonitrile at 80℃; for 0.5h; |
1. Introduction of Methenolone
Methenolone is one kind of white or almost white crystalline powder. The IUPAC Name of this chemical is (5S,8R,9S,10S,13S,14S,17S)-17-hydroxy-1,10,13-trimethyl-4,5,6,7,8,9,11,
12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one. Besides, Methenolone belongs to Steroids; Steroid and Hormone; Finished Steroid and Hormone. What's more, its systematic name is (5α,17β)-17-Hydroxy-1-methylandrost-1-en-3-one. Its classification codes are: (1)Anabolic Agents; (2)Hormones; (3)Hormones, Hormone Substitutes, and Hormone Antagonists.
This chemical is a synthetic steroid that has been used for its anabolic action. It is supplied as the acetate ester for oral administration and as the enanthate ester for intramuscular injection.
2. Properties of Methenolone
Physical properties about Methenolone are:
(1)ACD/LogP: 3.717; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 3.72; (4)ACD/LogD (pH 7.4): 3.72; (5)ACD/BCF (pH 5.5): 393.28; (6)ACD/BCF (pH 7.4): 393.28; (7)ACD/KOC (pH 5.5): 2505.49; (8)ACD/KOC (pH 7.4): 2505.49; (9)#H bond acceptors: 2; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 1; (12)Polar Surface Area: 37.3 Å2; (13)Index of Refraction: 1.542; (14)Molar Refractivity: 87.803 cm3; (15)Molar Volume: 278.897 cm3; (16)Polarizability: 34.808×10-24cm3; (17)Surface Tension: 40.06 dyne/cm; (18)Density: 1.084 g/cm3; (19)Flash Point: 183.597 °C; (20)Enthalpy of Vaporization: 79.187 kJ/mol; (21)Boiling Point: 430.381 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25°C.
3. Structure Descriptors of Methenolone
You can still convert the following datas into molecular structure:
(1)SMILES: O=C2\C=C(\C)[C@@]3([C@H]1CC[C@@]4([C@@H](O)CC[C@H]4[C@@H]1CC[C@H]3C2)C)C
(2)Std. InChI: InChI=1S/C20H30O2/c1-12-10-14(21)11-13-4-5-15-16-6-7-18(22)19(16,2)9-8-17(15)20(12,13)3/h10,13,15-18,22H,4-9,11H2,1-3H3/t13-,15-,16-,17-,18-,19-,20-/m0/s1
(3)Std. InChIKey: ANJQEDFWRSLVBR-VHUDCFPWSA-N
(4)Canonical SMILES : CC1=CC(=O)CC2C1(C3CCC4(C(C3CC2)CCC4O)C)C
(5)Isomeric SMILES: CC1=CC(=O)C[C@H]2[C@]1([C@H]3CC[C@]4([C@H]([C@@H]3CC2)CC[C@@H]4O)C)C
4. Physical Properties of Methenolone
Physical Property | Value | Units | Temp (deg C) | Source |
---|---|---|---|---|
log P (octanol-water) | 3.690 | (none) | EST | |
Atmospheric OH Rate Constant | 1.15E-10 | cm3/molecule-sec | 25 | EST |
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