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1449-61-2

Basic Information
CAS No.: 1449-61-2
Name: Androst-5-en-3-ol-7,17-dione acetate
Article Data: 50
Molecular Structure:
Molecular Structure of 1449-61-2 (Androst-5-en-3-ol-7,17-dione acetate)
Formula: C21H28O4
Molecular Weight: 344.451
Synonyms: Androst-5-ene-7,17-dione,3b-hydroxy-, acetate (6CI,7CI,8CI);3b-Acetoxy-5-androsten-7,17-dione;3b-Acetoxyandrost-5-ene-7,17-dione;3b-O-Acetyl-7-oxodehydroepiandrosterone;5-Androsten-3b-ol-7,17-dione acetate;7-Keto Naturalean;7-Oxodehydroepiandrosterone acetate;NSC 134911;
EINECS: 683-490-4
Density: 1.18 g/cm3
Melting Point: 184.5-187.5 °C
Boiling Point: 479.638 °C at 760 mmHg
Flash Point: 209.21 °C
PSA: 60.44000
LogP: 3.62900
Synthetic route
566-19-8

5-androstene-3β-ol-7,17-dione

108-24-7

acetic anhydride

1449-61-2

3-O-acetyl-7-oxo-dehydroepiandrosterone

Conditions
ConditionsYield
With toluene-4-sulfonic acid for 0.0333333h; microwave irradiation;96%
for 3h; Reflux;85%
853-23-6

prasterone acetate

1449-61-2

3-O-acetyl-7-oxo-dehydroepiandrosterone

Conditions
ConditionsYield
With N-hydroxyphthalimide; sodium dichromate; chromium(III) perchlorate In water; acetonitrile at 20℃; for 48h; Product distribution / selectivity;93%
With tert.-butylhydroperoxide; N-hydroxyphthalimide; cobalt(II) acetate In acetone at 20℃; for 5h; regioselective reaction;93.7%
Stage #1: prasterone acetate With tert.-butylhydroperoxide; 3 A molecular sieve In decane; ethyl acetate at 20℃; for 0.5h;
Stage #2: With manganese triacetate In decane; ethyl acetate at 20℃; for 30h;
91%
853-23-6

prasterone acetate

A

1449-61-2

3-O-acetyl-7-oxo-dehydroepiandrosterone

B

39933-10-3

3β,5-dihydroxy-5α-androstane-6,17-dione 3-acetate

C

6585-68-8

3β-acetoxy-5β,6β-epoxyandrostan-17-one

Conditions
ConditionsYield
With chromyl acetate In dichloromethane at -78℃; for 0.25h;A 30 mg
B 60 mg
C 77%
853-23-6

prasterone acetate

A

1449-61-2

3-O-acetyl-7-oxo-dehydroepiandrosterone

B

37976-94-6

7α-hydroxy-17-oxoandrost-5-ene-3β-yl acetate

Conditions
ConditionsYield
With tert.-butylhydroperoxide; manganese(IV) oxide In dichloromethane; water at -20℃; for 22h; Reflux; regioselective reaction;A 75%
B 13%
853-23-6

prasterone acetate

A

1449-61-2

3-O-acetyl-7-oxo-dehydroepiandrosterone

B

929270-02-0

(3S,6aR,6bS,9aS,11aS,11bR)-9a,11b-dimethyl-9-oxohexadecahydrocyclopenta[1,2]phenanthro[8a,9-b]oxiren-3-yl acetate

Conditions
ConditionsYield
With tert.-butylhydroperoxide; chromium(VI) oxide In dichloromethane for 24h; Ambient temperature;A 52%
B 8%
853-23-6

prasterone acetate

A

1449-61-2

3-O-acetyl-7-oxo-dehydroepiandrosterone

B

37976-94-6

7α-hydroxy-17-oxoandrost-5-ene-3β-yl acetate

C

6585-68-8

3β-acetoxy-5β,6β-epoxyandrostan-17-one

D

14545-93-8

5α,6α-epoxy-17-oxoandrostan-3β-yl acetate

Conditions
ConditionsYield
With ferric picolinate complexes; dihydrogen peroxide In acetonitrile for 3h; Ambient temperature;A 22%
B 39.3%
C 1.9%
D 0.7%
With ferric picolinate complexes; dihydrogen peroxide In acetonitrile for 3h; Ambient temperature;A 22%
B 39.3%
C 1.9%
D 0.7%
84412-82-8

3β-acetoxy-17-picolinylidene-androst-5-ene

1449-61-2

3-O-acetyl-7-oxo-dehydroepiandrosterone

Conditions
ConditionsYield
With chromium(VI) oxide In acetic anhydride; acetic acid at 90 - 95℃; for 1h;10.6%
84412-82-8

3β-acetoxy-17-picolinylidene-androst-5-ene

A

1449-61-2

3-O-acetyl-7-oxo-dehydroepiandrosterone

B

83830-40-4

3β-acetoxy-17-picolinylidene-5-androstene-7-one

Conditions
ConditionsYield
With chromium(VI) oxide In water; acetic acid at 90 - 95℃; for 1h;A 9.8%
B 8.9%
853-23-6

prasterone acetate

A

1449-61-2

3-O-acetyl-7-oxo-dehydroepiandrosterone

B

6585-68-8

3β-acetoxy-5β,6β-epoxyandrostan-17-one

C

14545-93-8

5α,6α-epoxy-17-oxoandrostan-3β-yl acetate

Conditions
ConditionsYield
With Mn(OTf)2(dMMpdp); dihydrogen peroxide; trimethylpyruvic acid In water; ethyl acetate; acetonitrile at 20℃; for 1h; Reagent/catalyst; diastereoselective reaction;A 8%
B n/a
C n/a
With Fe(OTf)2(dMMpdp); dihydrogen peroxide; trimethylpyruvic acid In water; ethyl acetate; acetonitrile at 20℃; for 1h; diastereoselective reaction;A 2%
B n/a
C n/a
853-23-6

prasterone acetate

A

1449-61-2

3-O-acetyl-7-oxo-dehydroepiandrosterone

B

98128-97-3

3β-acetoxy-5,20-dioxo-5,6-secoandrostan-6-oic acid

Conditions
ConditionsYield
With chromium(VI) oxide; acetic acid
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Specification

The Androst-5-en-3-ol-7,17-dione acetate, with CAS registry number 1449-61-2, belongs to the following product category: Pharmaceutical Raw Materials. It has the systematic name of 7,17-dioxoandrost-5-en-3-yl acetate. And its IUPAC name is (10,13-dimethyl-7,17-dioxo-2,3,4,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-3-yl) acetate. And the chemical formula of this chemical is C21H28O4.

Physical properties of Androst-5-en-3-ol-7,17-dione acetate: (1)ACD/LogP: 2.49; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.49; (4)ACD/LogD (pH 7.4): 2.49; (5)ACD/BCF (pH 5.5): 45.56; (6)ACD/BCF (pH 7.4): 45.56; (7)ACD/KOC (pH 5.5): 535.61; (8)ACD/KOC (pH 7.4): 535.61; (9)#H bond acceptors: 4; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 2; (12)Polar Surface Area: 60.44 Å2; (13)Index of Refraction: 1.548; (14)Molar Refractivity: 92.81 cm3; (15)Molar Volume: 291.9 cm3; (16)Polarizability: 36.79×10-24cm3; (17)Surface Tension: 45.3 dyne/cm; (18)Enthalpy of Vaporization: 74.4 kJ/mol; (19)Vapour Pressure: 2.32E-09 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: CC(=O)OC4CC[C@@]1(C)C(=C\C(=O)[C@H]2[C@@H]3CCC(=O)[C@@]3(C)CC[C@H]12)/C4
(2)InChI: InChI=1/C21H28O4/c1-12(22)25-14-6-8-20(2)13(10-14)11-17(23)19-15-4-5-18(24)21(15,3)9-7-16(19)20/h11,14-16,19H,4-10H2,1-3H3/t14?,15-,16-,19-,20-,21-/m0/s1
(3)InChIKey: VVSMJVQHDZUPIL-FQAVLMBTBQ
(4)Std. InChI: InChI=1S/C21H28O4/c1-12(22)25-14-6-8-20(2)13(10-14)11-17(23)19-15-4-5-18(24)21(15,3)9-7-16(19)20/h11,14-16,19H,4-10H2,1-3H3/t14?,15-,16-,19-,20-,21-/m0/s1
(5)Std. InChIKey: VVSMJVQHDZUPIL-FQAVLMBTSA-N