17 beta-Acetoxy-5 alpha-androstan-3-one

Base Information

• Chemical Name: 17 beta-Acetoxy-5 alpha-androstan-3-one
• CAS No.: 1164-92-7
• Molecular Formula: C21H32 O3
• Molecular Weight: 332.483
• European Community (EC) Number: 601-431-2
• NSC Number: 12878
• DSSTox Substance ID: DTXSID50893661
• Nikkaji Number: J947.837J
• Wikidata: Q81987734
• Mol file: 1164-92-7.mol

Synonyms:17 beta-Acetoxy-5 alpha-androstan-3-one;1164-92-7;EC 601-431-2;NSC 12878;Androstan-3-one, 17-(acetyloxy)-, (5.beta.,17.beta.)-;DTXSID50893661;NSC12878;NSC-12878;17beta-Acetoxy-5beta-androstane-3-one;17.beta.-Acetoxy-5.beta.-androstan-3-one

Chemical Property of 17 beta-Acetoxy-5 alpha-androstan-3-one

Chemical Property:

• Vapor Pressure: 2.04E-07mmHg at 25°C
• Boiling Point: 424.6°Cat760mmHg
• Flash Point: 182.8°C
• Density: 1.09g/cm³
• XLogP3: 4.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 332.23514488
• Heavy Atom Count: 24
• Complexity: 555

Purity/Quality:

99.9% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OC1CCC2C1(CCC3C2CCC4C3(CCC(=O)C4)C)C
• Isomeric SMILES: CC(=O)O[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC[C@H]4[C@@]3(CCC(=O)C4)C)C

Technology Process of 17 beta-Acetoxy-5 alpha-androstan-3-one

There total 9 articles about 17 beta-Acetoxy-5 alpha-androstan-3-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: 15.0%

testosterone acetate (1045-69-8) → stanolone acetate (1164-91-6) + 17β-acetoxy-5β-androstan-3-one (1164-92-7)

Guidance literature:

With NaY zeolite (Si/Al: 2.5); In hexane; Title compound not separated from byproducts; Irradiation;

DOI:10.1021/ja972976q

Reference yield:

Acetic acid (8R,9S,10S,13S,14S,17S)-3-hydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl ester → stanolone acetate (1164-91-6) + 17β-acetoxy-5β-androstan-3-one (1164-92-7)

Guidance literature:

With jones reagent; In acetone; for 0.0833333h; Yield given; Yields of byproduct given;

DOI:10.1135/cccc19981528

Reference yield:

1-((8R,9S,10R,13S,14S,17S)-17-Acetoxy-10,13-dimethyl-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-3-ylidene)-pyrrolidinium; perchlorate → stanolone acetate (1164-91-6) + 17β-acetoxy-5β-androstan-3-one (1164-92-7)

Guidance literature:

With 1-Benzyl-1,4-dihydronicotinamide; water; Multistep reaction. Yields of byproduct given; 1.) acetonitrile, 40 h, reflux 2.) acetonitrile, reflux, 1 h;

upstream raw materials:

testosterone acetate

Downstream raw materials:

17β-acetoxy-androsta-1,4-dien-3-one

3-Oxo-5β-androstan-16β-yl Benzoate

samanine

Refernces

• 1、 Jayathirtha Rao,Rajan Uppili,Corbin,Schwarz,Lustig,Ramamurthy. "Facial selective photoreduction of steroids: Role of zeolites". . p. 2480 - 2481. Retrieved 2007/10/03.
• 2、 Nishimura, Shigeo,Momma, Yasuhiro,Kawamura, Hideo,Shiota, Michio. "Stereochemistry of the Palladium-catalyzed Hydrogenation of 3-Oxo-4-ene Steroids. V. A Kinetic Study in Basic and Acidic Media". . p. 780 - 783. Retrieved 2007/10/02.