3beta-Hydroxy-androsta-5,15-dien-17-one Acetate

Base Information

• Chemical Name: 3beta-Hydroxy-androsta-5,15-dien-17-one Acetate
• CAS No.: 17921-64-1
• Molecular Formula: C₂₁H₂₈O₃
• Molecular Weight: 328.452
• Mol file: 17921-64-1.mol

Synonyms:3beta-Hydroxy-androsta-5,15-dien-17-one Acetate;SCHEMBL10274158;3beta-acetoxyandrosta-5,15-dien-17-one

Chemical Property of 3beta-Hydroxy-androsta-5,15-dien-17-one Acetate

Chemical Property:

• Melting Point: 179-181 °C(Solv: hexane (110-54-3))
• Boiling Point: 441.4±45.0 °C(Predicted)
• PSA: 43.37000
• Density: 1.13±0.1 g/cm3(Predicted)
• LogP: 4.22600
• XLogP3: 3.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 328.20384475
• Heavy Atom Count: 24
• Complexity: 646

Purity/Quality:

98% ^*data from raw suppliers

3β-O-Acetyl-androsta-5,15-dien-17-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OC1CCC2(C3CCC4(C(C3CC=C2C1)C=CC4=O)C)C
• Isomeric SMILES: CC(=O)O[C@H]1CC[C@@]2([C@H]3CC[C@]4([C@H]([C@@H]3CC=C2C1)C=CC4=O)C)C
• Uses: 3β-Hydroxy-androsta-5,15-dien-17-one Acetate is used in the preparation of Drospirenone.

Technology Process of 3beta-Hydroxy-androsta-5,15-dien-17-one Acetate

There total 5 articles about 3beta-Hydroxy-androsta-5,15-dien-17-one Acetate 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: 55.0%

prasterone acetate (853-23-6) → (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 (17921-64-1)

Guidance literature:

With copper(I) thiophene-2-carboxylate; di-tert-butyl peroxide; cyclohexyldiphenylphosphine; In benzene; at 80 ℃; for 12h; chemoselective reaction; Inert atmosphere; Sealed tube;

DOI:10.1021/jacs.9b07932

Reference yield: 49.0%

3β-hydroxy-androst-5,15-dien-17-one (17921-63-0) + acetic anhydride (108-24-7) → (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 (17921-64-1)

Guidance literature:

3β-hydroxy-androst-5,15-dien-17-one; acetic anhydride; With boron trifluoride diethyl etherate; In dichloromethane; at 20 ℃; for 2h;

With water; In dichloromethane;

Reference yield:

C29H43BO3 → (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 (17921-64-1)

Guidance literature:

With palladium diacetate; In diethyl ether; hexane; N,N-dimethyl acetamide; at 20 ℃; for 1h; stereoselective reaction; Molecular sieve; Inert atmosphere;

DOI:10.1002/chem.201604306

upstream raw materials:

3β-hydroxy-androst-5,15-dien-17-one

acetic anhydride

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

prasterone acetate

Downstream raw materials:

(3S,10R,13S)-10,13-dimethyl-17-(pyridin-3-yl)-2,3,4,7,8,9,10,11,12,13-decahydro-1H-cyclopenta[a]phenanthren-3-yl 2-(tert-butyl)benzoate

(3S,10R,13S)-10,13-dimethyl-17-(pyridin-3-yl)-2,3,4,7,8,9,10,11,12,13-decahydro-1H-cyclopenta[a]phenanthren-3-yl 2,6-dimethylbenzoate

3β-hydorxy-15β,16β-methylene androst-5-ene-17-one

Refernces

• 1、 Cerny, Ivan,Pouzar, Vladimir,Lapcik, Oldrich,Hampl, Richard. "Addition of azoimide to unsaturated ketones in the steroid series. Synthesis of N-(17β-hydroxy-3-oxo-5α-androstan-15β-yl)-succinamoic acid and its evaluation as hapten for dihydrotestosterone immunoanalysis". . p. 1931 - 1939. Retrieved 1997.
• 2、 Chen, Ming,Dong, Guangbin. "Copper-Catalyzed Desaturation of Lactones, Lactams, and Ketones under pH-Neutral Conditions". supporting information. p. 14889 - 14897. Retrieved 2019/10/02.
• 3、 Baranovskii,Bolibrukh,Gromak. "Synthesis of 14,16-dien-17-yl acetates of androstane series. NMR and mass spectrometry data". experimental part. p. 1877 - 1885. Retrieved 2012/01/07.