3alpha-Acetoxyandrostane-17-one

Base Information

• Chemical Name: 3alpha-Acetoxyandrostane-17-one
• CAS No.: 1164-95-0
• Molecular Formula: C21H32 O3
• Molecular Weight: 332.483
• European Community (EC) Number: 214-612-2
• Nikkaji Number: J3.274.684E
• Mol file: 1164-95-0.mol

Synonyms:Androsterone acetate;Androsterone, acetate;Androstan-17-one, 3-(acetyloxy)-, (3.alpha.,5.alpha.)-;SCHEMBL604252;3alpha-Acetoxyandrostane-17-one

Chemical Property of 3alpha-Acetoxyandrostane-17-one

Chemical Property:

• Vapor Pressure: 2.04E-07mmHg at 25°C
• Melting Point: 102-106 °C(Solv: ethyl ether (60-29-7); pentane (109-66-0))
• Boiling Point: 424.6°Cat760mmHg
• Flash Point: 182.8°C
• PSA: 43.37000
• Density: 1.09g/cm³
• LogP: 4.52990
• XLogP3: 4.3
• 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:

98%,99%, ^*data from raw suppliers

ANDROSTERONE ACETATE 98.00% ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn
• Statements: 40-48
• Safety Statements: 22-24/25-36/37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OC1CCC2(C(C1)CCC3C2CCC4(C3CCC4=O)C)C
• Isomeric SMILES: CC(=O)O[C@@H]1CC[C@@]2([C@H]3CC[C@]4([C@H]([C@@H]3CCC2C1)CCC4=O)C)C
• Uses: androgen

Technology Process of 3alpha-Acetoxyandrostane-17-one

There total 42 articles about 3alpha-Acetoxyandrostane-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: 100.0%

cis-androsterone (53-41-8) + acetic anhydride (108-24-7) → androsterone acetate (1164-95-0)

Guidance literature:

With toluene-4-sulfonic acid; for 0.025h; microwave irradiation;

DOI:10.1016/S0040-4020(03)00207-2

Reference yield: 98.0%

3α-Acetoxy-5α-androstan-17-one phenylhydrazone → androsterone acetate (1164-95-0)

Guidance literature:

With 3,3-dimethyldioxirane; In acetone; at 20 ℃; for 0.25h;

DOI:10.1021/jo00077a065

Reference yield: 91.9%

cesium acetate (3396-11-0) + (3β,5α)-3-[(methylsulfonyl)oxy]androstan-17-one (19646-53-8) → androsterone acetate (1164-95-0)

Guidance literature:

With 4-methyl-morpholine; 18-crown-6 ether; for 24h; Reflux; Inert atmosphere;

upstream raw materials:

3β-chloro-5α-androstan-17-one

potassium acetate

3β-tosyloxy-5α-androstan-17-one

(3α,5α)-3-(acetyloxy)pregnan-20-one

Downstream raw materials:

androstanediol

17β-hydroxy-5α-androstan-3α-yl acetate

Epiandrosterone

3β-acetoxy-5α-androstan-17-one

Refernces

• 1、 Iriarte et al.. "-". . p. 542,544. Retrieved 1955.
• 2、 Howell, Jennifer M.,Feng, Kaibo,Clark, Joseph R.,Trzepkowski, Louis J.,White, M. Christina. "Remote Oxidation of Aliphatic C-H Bonds in Nitrogen-Containing Molecules". supporting information. p. 14590 - 14593. Retrieved 2015/12/08.
• 3、 Garrido, Mariana,Peng, Hwei-Ming,Yoshimoto, Francis K.,Upadhyay, Sunil K.,Bratoeff, Eugene,Auchus, Richard J.. "A-ring modified steroidal azoles retaining similar potent and slowly reversible CYP17A1 inhibition as abiraterone". . p. 1 - 10. Retrieved 2014/04/03.