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6157-87-5

Basic Information
CAS No.: 6157-87-5
Name: Trestolone acetate
Article Data: 10
Cas Database
Molecular Structure:
Molecular Structure of 6157-87-5 (Trestolone acetate)
Formula: C21H30O3
Molecular Weight: 330.467
Synonyms: 19-Nortestosterone, 7alpha-methyl-, acetate;Estr-4-en-3-one, 17beta-hydroxy-7alpha-methyl-, acetate (8CI);17beta-Hydroxy-7alpha-methylestr-4-en-3-one acetate;19-Nortestosterone, 7.alpha.-methyl-, acetate;7.alpha.-Methyl-19-nortestosterone acetate;Estr-4-en-3-one, 17-(acetyloxy)-7-methyl-, (7.alpha.,17.beta.)-;Orgasteron acetate;(7,13-dimethyl-3-oxo-2,6,7,8,9,10,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl) acetate;[(7R,8R,9R,13S,14S,17S)-7,13-dimethyl-3-oxo-2,6,7,8,9,10,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl] acetate;Estr-4-en-3-one, 17.beta.-hydroxy-7.alpha.-methyl-, acetate;7-Methyl-3-oxoestr-4-en-17-yl acetate;Estr-4-en-3-one, 17-(acetyloxy)-7-methyl-, (7alpha,17beta)-;Estr-4-en-3-one, 17- (acetyloxy)-7-methyl-, (7.alpha.,17.beta.)-;[(7R,9R,14S,17S)-7,13-dimethyl-3-oxo-2,6,7,8,9,10,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl] acetate;17.beta.-Hydroxy-7.alpha.-methylestr-4-en-3-one acetate;
EINECS: N/A
Density: 1.117 g/cm3
Melting Point: 111-114 °C
Boiling Point: 447.571 °C at 760 mmHg
Flash Point: 194.228 °C
Solubility: N/A
Appearance: N/A
Hazard Symbols: N/A
Risk Codes: N/A
Safety:
Transport Information: N/A
PSA: 43.37000
LogP: 4.30590
Synthetic route
2590-41-2

6-dehydro-19-nortestosterone acetate

676-58-4

methylmagnesium chloride

6157-87-5

7alpha-Methyl-19-nortestosterone acetate

Conditions
ConditionsYield
Stage #1: 6-dehydro-19-nortestosterone acetate; methylmagnesium chloride; copper diacetate In tetrahydrofuran at -45 - -35℃; for 3h;
Stage #2: With hydrogenchloride In tetrahydrofuran; water at 10℃; for 0.5h;
78%
Stage #1: 6-dehydro-19-nortestosterone acetate; methylmagnesium chloride; copper(l) chloride In tetrahydrofuran at -30℃; for 3 - 4h;
Stage #2: With sulfuric acid; water In tetrahydrofuran for 1.33333h;

7alpha-Methyl-19-nortestosterone acetate

7alpha-Methyl-19-nortestosterone acetate

Conditions
ConditionsYield
Stage #1: zirconocene methyl chloride With silver trifluoromethanesulfonate; copper(l) chloride; (3,5-dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-(1-phenyl-ethyl)-amine In diethyl ether; dichloromethane at 20℃; for 0.166667h; Darkness; Inert atmosphere;
Stage #2: 6-dehydro-19-nortestosterone acetate With chloro-trimethyl-silane In diethyl ether; dichloromethane at 20℃; for 15h; Inert atmosphere; Darkness; stereoselective reaction;
61%
2590-41-2

6-dehydro-19-nortestosterone acetate

676-58-4

methylmagnesium chloride

6157-87-5

7alpha-Methyl-19-nortestosterone acetate

Conditions
ConditionsYield
Stage #1: 6-dehydro-19-nortestosterone acetate; methylmagnesium chloride; copper diacetate In tetrahydrofuran at -45 - -35℃; for 3h;
Stage #2: With hydrogenchloride In tetrahydrofuran; water at 10℃; for 0.5h;
78%
Stage #1: 6-dehydro-19-nortestosterone acetate; methylmagnesium chloride; copper(l) chloride In tetrahydrofuran at -30℃; for 3 - 4h;
Stage #2: With sulfuric acid; water In tetrahydrofuran for 1.33333h;

zirconocene methyl chloride

2590-41-2

6-dehydro-19-nortestosterone acetate

6157-87-5

7alpha-Methyl-19-nortestosterone acetate

Conditions
ConditionsYield
Stage #1: zirconocene methyl chloride With silver trifluoromethanesulfonate; copper(l) chloride; (3,5-dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-(1-phenyl-ethyl)-amine In diethyl ether; dichloromethane at 20℃; for 0.166667h; Darkness; Inert atmosphere;
Stage #2: 6-dehydro-19-nortestosterone acetate With chloro-trimethyl-silane In diethyl ether; dichloromethane at 20℃; for 15h; Inert atmosphere; Darkness; stereoselective reaction;
61%
54793-00-9

17β-hydroxy-7α-methyl-estr-5-en-3-one acetate

6157-87-5

7alpha-Methyl-19-nortestosterone acetate

Conditions
ConditionsYield
With toluene-4-sulfonic acid In benzene
3764-87-2

7α-methyl-19-nortestosterone

75-36-5

acetyl chloride

6157-87-5

7alpha-Methyl-19-nortestosterone acetate

Conditions
ConditionsYield
With pyridine at 20℃;
434-22-0

19-nortestosterone

6157-87-5

7alpha-Methyl-19-nortestosterone acetate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: AcCl
2: (i) NBS, Py, aq. NaOAc, AcOH, acetone, (ii) LiBr, Li2CO3, DMF
3: (i) CuI, Et2O, (ii) /BRN= 3121674/, THF
4: TsOH / benzene
View Scheme
4999-76-2

3,17β-diacetoxy-estra-3,5-diene

6157-87-5

7alpha-Methyl-19-nortestosterone acetate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: (i) NBS, Py, aq. NaOAc, AcOH, acetone, (ii) LiBr, Li2CO3, DMF
2: (i) CuI, Et2O, (ii) /BRN= 3121674/, THF
3: TsOH / benzene
View Scheme
2590-41-2

6-dehydro-19-nortestosterone acetate

6157-87-5

7alpha-Methyl-19-nortestosterone acetate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: (i) CuI, Et2O, (ii) /BRN= 3121674/, THF
2: TsOH / benzene
View Scheme

C24H38O3Si

6157-87-5

7alpha-Methyl-19-nortestosterone acetate

Conditions
ConditionsYield
With water In tetrahydrofuran at 20℃; for 24h; Inert atmosphere;
Downstream Products
3764-87-2
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    Name: Triptolone Acetate Alias: Triptolone Acetate English name: trestolone acetate English alias: Trestolone acetate [USAN]; Trestolone acetate; CAS No. 6157-87-5 Molecular formula: C21H3003 Molecular weight: 330.4611

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Specification

The Trestolone acetate, with the CAS registry number 6157-87-5, is also known as 7α-Methyl-19-nortestosterone acetate. This chemical's molecular formula is C21H30O3 and molecular weight is 330.47. What's more, its systematic name is called (7α,17β)-7-Methyl-3-oxoestr-4-en-17-yl acetate.

Physical properties about Trestolone acetate are: (1)ACD/LogP: 4.399; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 4.40; (4)ACD/LogD (pH 7.4): 4.40; (5)ACD/BCF (pH 5.5): 1297.76; (6)ACD/BCF (pH 7.4): 1297.76; (7)ACD/KOC (pH 5.5): 5888.75; (8)ACD/KOC (pH 7.4): 5888.75; (9)#H bond acceptors: 3; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 2; (12)Polar Surface Area: 43.37 Å2; (13)Index of Refraction: 1.539; (14)Molar Refractivity: 92.643 cm3; (15)Molar Volume: 295.841 cm3; (16)Polarizability: 36.727×10-24cm3; (17)Surface Tension: 41.729 dyne/cm; (18)Density: 1.117 g/cm3; (19)Flash Point: 194.228 °C; (20)Enthalpy of Vaporization: 70.593 kJ/mol; (21)Boiling Point: 447.571 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25 °C.

You can still convert the following datas into molecular structure:
(1) SMILES: O=C4\C=C2/[C@@H]([C@H]1CC[C@@]3([C@@H](OC(=O)C)CC[C@H]3[C@@H]1[C@H](C)C2)C)CC4
(2) InChI: InChI=1S/C21H30O3/c1-12-10-14-11-15(23)4-5-16(14)17-8-9-21(3)18(20(12)17)6-7-19(21)24-13(2)22/h11-12,16-20H,4-10H2,1-3H3/t12-,16+,17-,18+,19+,20-,21+/m1/s1
(3) InChIKey: IVCRCPJOLWECJU-XQVQQVTHSA-N