3beta-Hydroxyandrosta-5,15-dien-17-one

Base Information

• Chemical Name: 3beta-Hydroxyandrosta-5,15-dien-17-one
• CAS No.: 17921-63-0
• Molecular Formula: C19H26 O2
• Molecular Weight: 286.414
• DSSTox Substance ID: DTXSID10453588
• Nikkaji Number: J697.669G
• Mol file: 17921-63-0.mol

Synonyms:3beta-hydroxyandrosta-5,15-dien-17-one;17921-63-0;5,15-ANDROSTDIENE-3-HYDROXY-17-ONE;(3S,8R,9S,10R,13S,14S)-3-hydroxy-10,13-dimethyl-1,2,3,4,7,8,9,11,12,14-decahydrocyclopenta[a]phenanthren-17-one;(3aS,3bR,7S,9aR,9bS,11aS)-7-hydroxy-9a,11a-dimethyl-1H,3aH,3bH,4H,6H,7H,8H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-1-one;SCHEMBL6574830;DTXSID10453588;XGAZYVFYLADCPH-USOAJAOKSA-N

Chemical Property of 3beta-Hydroxyandrosta-5,15-dien-17-one

Chemical Property:

• PSA: 37.30000
• LogP: 3.65520
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 286.193280068
• Heavy Atom Count: 21
• Complexity: 546

Purity/Quality:

99% ^*data from raw suppliers

3β-Hydroxyandrosta-5,15-dien-17-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCC(CC1=CCC3C2CCC4(C3C=CC4=O)C)O
• Isomeric SMILES: C[C@]12CC[C@@H](CC1=CC[C@@H]3[C@@H]2CC[C@]4([C@H]3C=CC4=O)C)O
• Uses: 5,15-ANDROSTDIENE-3-HYDROXY-17-ONE is used in the preparation of Drospirenone.

Technology Process of 3beta-Hydroxyandrosta-5,15-dien-17-one

There total 18 articles about 3beta-Hydroxyandrosta-5,15-dien-17-one which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 92.0%

17,17-ethylenedioxy-3β-hydroxyandrosta-5,15-diene (17921-62-9) → 3β-hydroxy-androst-5,15-dien-17-one (17921-63-0)

Guidance literature:

With toluene-4-sulfonic acid; In acetone; at 15 ℃; for 19h;

Reference yield: 75.0%

17,17-ethylenedioxy-3β-hydroxyandrosta-5,15-diene (17921-62-9) → 3β-hydroxy-androst-5,15-dien-17-one (17921-63-0) + 3β-hydroxyandrosta-5,14-dien-17-one (34635-41-1)

Guidance literature:

With toluene-4-sulfonic acid; In water; acetone; for 18h; Inert atmosphere;

DOI:10.1134/S1070363211090234

Reference yield: 57.0%

3β-hydroxy-16ξ-phenylsulfinyl-5β-androsten-17-one (111119-50-7) → 3β-hydroxy-androst-5,15-dien-17-one (17921-63-0)

Guidance literature:

With N,N-dimethyl-aniline; In xylene; for 15h; Heating;

upstream raw materials:

17,17-ethylenedioxy-3β-hydroxyandrosta-5,15-diene

3β-hydroxy-16ξ-phenylsulfinyl-5β-androsten-17-one

3β-hydroxy-16α-(phenylseleno)androst-5-en-17-one

dehydroepiandrosterone

Downstream raw materials:

3-((3S,8R,9S,10R,13S,14S,15R)-3-Hydroxy-10,13-dimethyl-17-oxo-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-15-ylsulfanyl)-propionic acid

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

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

(3S,8R,9S,10R,13S,14S)-10,13-dimethyl-17-oxo-2,3,4,7,8,9,10,11,12,13,14,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate