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Basic Information
CAS No.: 640-87-9
Name: REICHSTEIN'S SUBSTANCE S 21-ACETATE
Molecular Structure:
Molecular Structure of 640-87-9 (REICHSTEIN'S SUBSTANCE S 21-ACETATE)
Formula: C23H32 O5
Molecular Weight: 388.504
Synonyms: Corticosterone,11-deoxy-17-hydroxy-, 21-acetate (6CI); Pregn-4-ene-3,20-dione,17,21-dihydroxy-, 21-acetate (8CI); 11-Deoxycortisol 21-acetate;17,21-Dihydroxypregn-4-ene-3,20-dione 21-acetate;17-Hydroxy-21-acetoxyprogesterone; 17a-Hydroxy-11-deoxycorticosterone-21-acetate;21-Acetoxy-17-hydroxypregn-4-ene-3,20-dione; 21-Acetoxy-17a-hydroxyprogesterone; 4-Pregnene-17a,21-diol-3,20-dione 21-acetate;Cortexolone 21-acetate; Cortodoxon 21-acetate; NSC 81196; Reichstein substanceS 21-acetate; Reichstein-S-acetate; Reichstein's substance S 21-acetate;Reichstein's substance S acetate
Density: 1.4 g/cm3
Melting Point: 233-235°C
Boiling Point: 537.9±50.0 °C(Predicted)
Flash Point: 181.8oC
PSA: 80.67000
LogP: 3.38160
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Synthetic route
152-58-9

Cortexolone

108-24-7

acetic anhydride

640-87-9

cortexolone 21-acetate

Conditions
ConditionsYield
With pyridine at 20℃; for 0.5h;100%
With pyridine
68-96-2

17-hydroxyprogesterone

108-24-7

acetic anhydride

640-87-9

cortexolone 21-acetate

Conditions
ConditionsYield
Stage #1: 17-hydroxyprogesterone With calcium chloride; calcium oxide In methanol; chloroform for 2h;
Stage #2: acetic anhydride With potassium carbonate; acetic acid In methanol; chloroform; N,N-dimethyl-formamide at 100℃; for 1h;		98%
68-96-2

17-hydroxyprogesterone

127-08-2

potassium acetate

640-87-9

cortexolone 21-acetate

Conditions
ConditionsYield
Stage #1: 17-hydroxyprogesterone With pyrrolidine In ethanol at 0 - 50℃;
Stage #2: potassium acetate With acetic acid; potassium iodide In ethanol; acetone at 20 - 60℃;		98%
4470-79-5

21-Iodo-17α-hydroxypregn-4-en-3,20-dione

64-19-7

acetic acid

640-87-9

cortexolone 21-acetate

Conditions
ConditionsYield
With triethylamine In acetone for 5h; Heating; Inert atmosphere;97%
108-22-5

Isopropenyl acetate

152-58-9

Cortexolone

640-87-9

cortexolone 21-acetate

Conditions
ConditionsYield
With Rhizopus oryzae lipase immobilized on Lewatit 1600 resin In di-isopropyl ether at 55℃; for 48h; regioselective reaction;91%
20380-16-9

17α-hydroxy-21-chloro-4-pregnene-3,20-dione

127-08-2

potassium acetate

640-87-9

cortexolone 21-acetate

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 80℃; for 0.5h;90%
20380-17-0

21-bromo-17α-hydroxy-4-pregnene-3,20-dione

127-08-2

potassium acetate

640-87-9

cortexolone 21-acetate

Conditions
ConditionsYield
In acetone at 50℃; for 1h;86%
Yield given;
1474-10-8

3β,17α,21-trihydroxypregn-5-en-20-one 21-acetate

A

640-87-9

cortexolone 21-acetate

B

Acetic acid 2-((8R,9S,10R,13S,14S,17R)-17-hydroxy-10,13-dimethyl-3-oxo-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-2-oxo-ethyl ester

Conditions
ConditionsYield
With <(C4Ph4COHOCC4Ph4)(μ-H)><(CO)4Ru2>; acetone at 56℃; for 24h;A 67%
B 28%
19357-45-0

17α,21-dihydroxy-4-pregnene-3,20-dione 17-acetate

640-87-9

cortexolone 21-acetate

Conditions
ConditionsYield
With potassium acetate In N,N-dimethyl-formamide at 105℃; for 6h;51%
88261-15-8

21-acetoxy-20-cyanopregna-4,17(20)-dien-3-one

640-87-9

cortexolone 21-acetate

Conditions
ConditionsYield
With potassium permanganate; N-benzyl-N,N,N-triethylammonium chloride In dichloromethane Ambient temperature;28%
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