3-Oxoandrostan-17-yl acetate

Base Information

• Chemical Name: 3-Oxoandrostan-17-yl acetate
• CAS No.: 1164-91-6
• Molecular Formula: C21H32 O3
• Molecular Weight: 332.483
• NSC Number: 73107
• Mol file: 1164-91-6.mol

Synonyms:5.alpha.-Dihydrotestosterone acetate;NSC-73107;5.alpha.,17.beta.-Dihydrotestosterone ethanoate;Oprea1_406278;3-Oxoandrostan-17-yl acetate;SCHEMBL23363784;ILCTUFVQFCIIDS-UHFFFAOYSA-N;NSC73107;5.alpha.-Androstan-3-one, acetate;STK366317;AKOS003406220;FT-0662171

Chemical Property of 3-Oxoandrostan-17-yl acetate

Chemical Property:

• Vapor Pressure: 2.04E-07mmHg at 25°C
• Refractive Index: 1.6000 (estimate)
• Boiling Point: 424.6°C at 760 mmHg
• Flash Point: 182.8°C
• PSA: 43.37000
• Density: 1.09g/cm³
• LogP: 4.52990
• Water Solubility.: 88.84g/L(temperature not stated)
• 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:

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

17-O-AcetylAndrostanoloneDiscontinued,seeA637615 ^*data from reagent 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
• Uses: Anabolic steroid.

Technology Process of 3-Oxoandrostan-17-yl acetate

There total 29 articles about 3-Oxoandrostan-17-yl 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: 99.0%

Stanolone (521-18-6) + acetic anhydride (108-24-7) → stanolone acetate (1164-91-6)

Guidance literature:

With pyridine; dmap; at 20 ℃; for 6h; Inert atmosphere;

DOI:10.1021/np300069z

Reference yield: 98.3%

Stanolone (521-18-6) + acetyl chloride (75-36-5) → stanolone acetate (1164-91-6)

Guidance literature:

With pyridine; In dichloromethane; for 2h; Ambient temperature;

DOI:10.1021/jm00089a024

Reference yield: 97.0%

(5α,17β)-3-oxoandrost-1-en-17-yl acetate (64-82-4,6656-41-3,21507-42-6,25615-33-2,54631-35-5,79732-37-9,97413-69-9) → stanolone acetate (1164-91-6)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tributylzinc hydride; In tetrahydrofuran; for 1h; Heating;

upstream raw materials:

(5S,8R,9S,10S,13S,14S,17S)-10,13-dimethyl-4,5,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,17-diyl diacetate

17β-acetoxy-5α-androstan-3α-ol

5α-androstane-3-β,17β-diol 17-acetate

17β-acetoxy-5α-androstan-3-one-diethylacetal

Downstream raw materials:

(5S,8R,9S,10S,13S,14S,17S)-10,13-dimethyl-4,5,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,17-diyl diacetate

17β-acetoxy-2α-bromo-5α-androstan-3-one

2-hydroxymethylene-17β-hydroxy-5α-androstan-3-one

17β-(acetyloxy)-3-oxa-A-homo-5α-androstan-4-one

Refernces

• 1、 Sidova, Romana,Stransky, Karel,Kasal, Alexander,Slavikova, Barbora,Kohout, Ladislav. "Long-range effect of 17-substituents in 3-oxo steroids on 4,5-double bond hydrogenation". . p. 1528 - 1542. Retrieved 1998.
• 2、 Liu,Carlson,Katzenellenbogen. "Synthesis of high affinity fluorine-substituted ligands for the androgen receptor. Potential agents for imaging prostatic cancer by positron emission tomography". . p. 2113 - 2129. Retrieved 1992.
• 3、 Jayathirtha Rao,Rajan Uppili,Corbin,Schwarz,Lustig,Ramamurthy. "Facial selective photoreduction of steroids: Role of zeolites". . p. 2480 - 2481. Retrieved 1998.
• 4、 Liston,Howarth. "". . p. 2577,2581. Retrieved 1967.
• 5、 Shi, Shasha,Yang, Xianyu,Tang, Man,Hu, Jiefeng,Loh, Teck-Peng. "Direct Synthesis of α-Amino Nitriles from Sulfonamides via Base-Mediated C-H Cyanation". supporting information. p. 4018 - 4022. Retrieved 2021/05/26.
• 6、 Thibeault, Dominic,Roy, Jenny,DeRoy, Patrick,Poirier, Donald. "Chemical synthesis of 2β-amino-5α-androstane-3α,17β-diol N-derivatives and their antiproliferative effect on HL-60 human leukemia cells". . p. 5062 - 5077. Retrieved 2008/12/22.