10448-96-1

Usage

Uses

Used in Medical Applications:
Almestrone is used as a therapeutic agent for treating conditions such as muscle wasting, osteoporosis, and hormonal imbalances. It is used for promoting the growth and development of muscle tissue, increasing bone density, and stimulating secondary sexual characteristics in men.
Used in Hormonal Imbalance Treatment:
Almestrone is used as a hormone replacement therapy for individuals suffering from hormonal imbalances. It helps in restoring normal hormonal levels and alleviating symptoms associated with hormonal deficiencies.
Used in Muscle Wasting Treatment:
Almestrone is used as an anabolic agent for treating muscle wasting conditions, where it promotes muscle growth and development, improving muscle mass and strength.
Used in Osteoporosis Treatment:
Almestrone is used as a bone density enhancer for treating osteoporosis, where it helps in increasing bone density and reducing the risk of fractures.
Used in Sports and Bodybuilding:
Almestrone is used as a performance-enhancing drug in sports and bodybuilding, where it is taken to increase muscle mass, strength, and endurance. However, its use in this context is illegal and can lead to serious health risks and legal consequences.

InChI:InChI=1/C19H24O2/c1-11-9-12-10-13(20)3-4-14(12)15-7-8-19(2)16(18(11)15)5-6-17(19)21/h3-4,10-11,15-16,18,20H,5-9H2,1-2H3

Synthetic route

4-estrene-7α-methyl-3,17-dione → 7α-Methylestrone (10448-96-1)

Conditions	Yield
With oxygen; copper(ll) bromide In acetonitrile at 40℃; for 1.5 - 26h; Quantum yield;	73%
With oxygen; copper dichloride In acetonitrile at 40℃; for 5h;	52%
With copper(ll) bromide In acetinitrile at 40℃; for 18h;

7α-Methylestrone (10448-96-1) + methyl iodide (74-88-4) → 4-methoxy 7α-methylestrone

Conditions	Yield
With potassium carbonate In dichloromethane; water; acetone	100%

trifluoromethylsulfonic anhydride (358-23-6) + 7α-Methylestrone (10448-96-1) → 7α-methyl-3-trifluoromethanesylfonyloxyestra-1,3,5(10)-trien-17-one (156078-51-2)

Conditions	Yield
With 2,6-dimethylpyridine In diethyl ether; dichloromethane at 0℃; for 0.666667h;	96%

Isopropenyl acetate (108-22-5) + 7α-Methylestrone (10448-96-1) → 7α-methylestrone acetate (36014-09-2) + 7α-methylestra-1,3,5(10),16-tetraene-3,17-diol diacetate (28838-19-9)

Conditions	Yield
With sulfuric acid for 2h; Heating;	A 23% B 54%

7α-Methylestrone (10448-96-1) → 16α-bromo-3-hydroxy-7α-methylestra-1,3,5(10)-trien-17-one (146016-30-0)

Conditions	Yield
With copper(ll) bromide In chloroform; ethyl acetate for 3h; Heating;
Multi-step reaction with 3 steps 1: 54 percent / H2SO4 / 2 h / Heating 2: 65 percent / acetate buffer, Br2 / acetic acid; diethyl ether / 0.25 h / 0 °C 3: 74.5 percent / conc. H2SO4 / ethanol / Ambient temperature View Scheme

7α-Methylestrone (10448-96-1) → 4-fluoro-7α-methylestrone (151160-22-4) + 2-fluoro-7α-methylestrone (151160-20-2)

Conditions	Yield
With N-fluoropyridinium triflate In 1,1,2-trichloroethane Heating; Title compound not separated from byproducts;

7α-Methylestrone (10448-96-1) → 16α-bromo-7α-methyl-3-trifluoromethanesulfonylestra-1,3,5(10)-trien-17-one (156078-53-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: 96 percent / 2,6-lutidine / CH2Cl2; diethyl ether / 0.67 h / 0 °C 2: 85 percent / conc. H2SO4 / 3.5 h / Heating 3: 77 percent / N-bromosuccinimide (NBS) / CCl4 / 21 h / Ambient temperature View Scheme

7α-Methylestrone (10448-96-1) → 7α-methyl-3-trifluoromethanesylfonyloxy-17-acetoxyestra-1,3,5(10),16-tetraene (156078-52-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: 96 percent / 2,6-lutidine / CH2Cl2; diethyl ether / 0.67 h / 0 °C 2: 85 percent / conc. H2SO4 / 3.5 h / Heating View Scheme

7α-Methylestrone (10448-96-1) → (7R,8R,9S,13S,14S,16R,17S)-16-Fluoro-7,13-dimethyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene-3,17-diol

Conditions

Yield

Multi-step reaction with 8 steps 1: 96 percent / 2,6-lutidine / CH2Cl2; diethyl ether / 0.67 h / 0 °C 2: 85 percent / conc. H2SO4 / 3.5 h / Heating 3: 77 percent / N-bromosuccinimide (NBS) / CCl4 / 21 h / Ambient temperature 4: 58 percent / 1 N aq. NaOH / tetrahydrofuran / 1.5 h / Ambient temperature 5: 95 percent / 2,6-lutidine / CH2Cl2 / 0.67 h / 0 °C 6: 81 percent / (n-Bu)4NF / tetrahydrofuran / 0.17 h / Ambient temperature 7: 29 percent / KOH / methanol / 5 h / Ambient temperature 8: 27 percent / LiAlH4 / diethyl ether / 0.25 h / -78 °C View Scheme

7α-Methylestrone (10448-96-1) → (7R,8R,9S,13S,14S,16R,17R)-16-Fluoro-7,13-dimethyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene-3,17-diol

Conditions

Yield

Multi-step reaction with 8 steps 1: 96 percent / 2,6-lutidine / CH2Cl2; diethyl ether / 0.67 h / 0 °C 2: 85 percent / conc. H2SO4 / 3.5 h / Heating 3: 77 percent / N-bromosuccinimide (NBS) / CCl4 / 21 h / Ambient temperature 4: 58 percent / 1 N aq. NaOH / tetrahydrofuran / 1.5 h / Ambient temperature 5: 95 percent / 2,6-lutidine / CH2Cl2 / 0.67 h / 0 °C 6: 81 percent / (n-Bu)4NF / tetrahydrofuran / 0.17 h / Ambient temperature 7: 29 percent / KOH / methanol / 5 h / Ambient temperature 8: 66 percent / LiAlH4 / diethyl ether / 0.25 h / -78 °C View Scheme

7α-Methylestrone (10448-96-1) → [18F]-16beta-Fluoro-7alpha-methylestradiol

Conditions

Yield

Multi-step reaction with 7 steps 1: 96 percent / 2,6-lutidine / CH2Cl2; diethyl ether / 0.67 h / 0 °C 2: 85 percent / conc. H2SO4 / 3.5 h / Heating 3: 77 percent / N-bromosuccinimide (NBS) / CCl4 / 21 h / Ambient temperature 4: 58 percent / 1 N aq. NaOH / tetrahydrofuran / 1.5 h / Ambient temperature 5: 95 percent / 2,6-lutidine / CH2Cl2 / 0.67 h / 0 °C 6: 81 percent / (n-Bu)4NF / tetrahydrofuran / 0.17 h / Ambient temperature 7: 95 percent / LiAlH4 / tetrahydrofuran / 1.) -78 deg C, 15 min, 2.) from 0 deg C to RT, 25 min View Scheme

7α-Methylestrone (10448-96-1) → (7R,8R,9S,13S,14S,16R)-16-Fluoro-3-hydroxy-7,13-dimethyl-6,7,8,9,11,12,13,14,15,16-decahydro-cyclopenta[a]phenanthren-17-one (156078-59-0)

Conditions

Yield

Multi-step reaction with 7 steps 1: 96 percent / 2,6-lutidine / CH2Cl2; diethyl ether / 0.67 h / 0 °C 2: 85 percent / conc. H2SO4 / 3.5 h / Heating 3: 77 percent / N-bromosuccinimide (NBS) / CCl4 / 21 h / Ambient temperature 4: 58 percent / 1 N aq. NaOH / tetrahydrofuran / 1.5 h / Ambient temperature 5: 95 percent / 2,6-lutidine / CH2Cl2 / 0.67 h / 0 °C 6: 81 percent / (n-Bu)4NF / tetrahydrofuran / 0.17 h / Ambient temperature 7: 29 percent / KOH / methanol / 5 h / Ambient temperature View Scheme

7α-Methylestrone (10448-96-1) → (7R,8R,9S,13S,14S,16S)-16-Fluoro-3-hydroxy-7,13-dimethyl-6,7,8,9,11,12,13,14,15,16-decahydro-cyclopenta[a]phenanthren-17-one

Conditions

Yield

Multi-step reaction with 7 steps 1: 96 percent / 2,6-lutidine / CH2Cl2; diethyl ether / 0.67 h / 0 °C 2: 85 percent / conc. H2SO4 / 3.5 h / Heating 3: 77 percent / N-bromosuccinimide (NBS) / CCl4 / 21 h / Ambient temperature 4: 58 percent / 1 N aq. NaOH / tetrahydrofuran / 1.5 h / Ambient temperature 5: 95 percent / 2,6-lutidine / CH2Cl2 / 0.67 h / 0 °C 6: 81 percent / (n-Bu)4NF / tetrahydrofuran / 0.17 h / Ambient temperature 7: 30 percent / KOH / methanol / 5 h / Ambient temperature View Scheme

Relevant academic research and scientific papers

PROCESS FOR PRODUCTION OF STEROID COMPOUND

The present invention relates to a process for production of a steroid compound having a partial structure represented by Formula (2) by oxidizing a steroid compound having a partial structure represented by Formula (1), without the need of any special apparatus, in a safe and economical manner, with less adverse affect on environment, in a simple and high efficient manner. Specifically, the invention relates to a process for producing a steroid compound having a partial structure of ring A and ring B of the steroid skeleton represented by Formula (2): wherein R represents a hydrogen atom or C1-6 alkyl group, comprising the step of reacting a steroid compound having a partial structure of ring A and ring B of the steroid skeleton represented by Formula (1): wherein R is the same as above; with a catalytic amount of copper halide in the presence of oxygen.