5alpha-Androstan-17-one

Base Information

• Chemical Name: 5alpha-Androstan-17-one
• CAS No.: 963-74-6
• Molecular Formula: C19H30O
• Molecular Weight: 274.447
• European Community (EC) Number: 213-516-8
• NSC Number: 90582
• DSSTox Substance ID: DTXSID001315767
• Nikkaji Number: J80.045G
• ChEMBL ID: CHEMBL2057976
• Mol file: 963-74-6.mol

Synonyms:5 alpha-androstan-17-one;androstan-17-one

Chemical Property of 5alpha-Androstan-17-one

Chemical Property:

• Vapor Pressure: 1.27E-05mmHg at 25°C
• Refractive Index: 1.517
• Boiling Point: 368.5 °C at 760 mmHg
• Flash Point: 168.7 °C
• PSA: 17.07000
• Density: 1.014 g/cm³
• LogP: 4.98830
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 5.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 274.229665576
• Heavy Atom Count: 20
• Complexity: 428

Purity/Quality:

99% ^*data from raw suppliers

5-alpha-Androstan-17-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCCCC1CCC3C2CCC4(C3CCC4=O)C
• Isomeric SMILES: C[C@]12CCCC[C@@H]1CC[C@@H]3[C@@H]2CC[C@]4([C@H]3CCC4=O)C

Technology Process of 5alpha-Androstan-17-one

There total 55 articles about 5alpha-Androstan-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: 95.0%

(3S,5S,8R,9S,10S,13S,14S)-3-bromo-10,13-dimethylhexadecahydro-17H-cyclopenta[a]phenanthren-17-one (58507-05-4) → 5alpha-androstan-17-one (963-74-6)

Guidance literature:

With water; zinc; In acetonitrile; at 80 ℃; for 36h; Sealed tube; Inert atmosphere;

DOI:10.1021/acs.joc.9b02026

Reference yield: 95.0%

Acetyl-thiocarbamic acid O-((3R,5S,8R,9S,10S,13S,14S)-10,13-dimethyl-17-oxo-hexadecahydro-cyclopenta[a]phenanthren-3-yl) ester (158299-72-0) → 5alpha-androstan-17-one (963-74-6)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In benzene; at 80 ℃; for 1h;

DOI:10.1055/s-1994-25536

Reference yield: 93.0%

3α-iodo-5αH-androstan-17-one (75980-93-7) → 5alpha-androstan-17-one (963-74-6)

Guidance literature:

With formic acid; zinc; In water; at 85 ℃; for 4.6h;

DOI:10.3184/174751914X13968892307636

upstream raw materials:

10,13-Dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-ol

(5R,8R,9S,10S,13S,14S,17S)-10,13-Dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-ol

cholestane

allopregnan-20-one

Downstream raw materials:

17-(hydroxyimino)-5α-androstane

5α-Androstan-17-on-p-toluolsulfonylhydrazon

17a-oxa-D-homo-5α-androstan-17-one

(5R,8R,9S,10S,13S,14S,17S)-10,13-Dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-ol

Refernces

• 1、 Crittenden, Christopher M.,Di Pasquale, Antonio G.. "Two crystallographic forms and the absolute structure of 5α,14α-androstane". . p. 537 - 543. Retrieved 2021/09/13.
• 2、 -. "Method for hydrogenolysis of halides". Paragraph 0232; 0254-0256. . Retrieved 2021/01/11.