17-beta-Hydroxy-5alpha-androst-1-en-3-one acetate

Base Information

• Chemical Name: 17-beta-Hydroxy-5alpha-androst-1-en-3-one acetate
• CAS No.: 64-82-4
• Molecular Formula: C₂₁H₃₀O₃
• Molecular Weight: 330.467
• European Community (EC) Number: 200-595-9
• DSSTox Substance ID: DTXSID60981907
• Nikkaji Number: J213.550G
• Mol file: 64-82-4.mol

Synonyms:64-82-4;17-beta-Hydroxy-5alpha-androst-1-en-3-one acetate;EINECS 200-595-9;[(5S,8R,9S,10R,13S,14S,17S)-10,13-dimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl] acetate;17beta-acetoxy-3-oxo-5alpha-androst-1-ene;SCHEMBL7196987;DTXSID60981907;NKZLRJOJLCHNQR-NGFSFWIMSA-N;3-Oxoandrost-1-en-17-yl acetate;17beta-acetoxy-5alpha-androst-1-en-3-one;17beta-(Acetyloxy)-5alpha-androst-1-en-3-one;17-beta-hydroxy-5alpha-androst-1-en-3-onacetat;Androst-1-en-3-one, 17-(acetyloxy)-, (5alpha,17beta)-

Chemical Property of 17-beta-Hydroxy-5alpha-androst-1-en-3-one acetate

Chemical Property:

• PSA: 43.37000
• LogP: 4.30590
• XLogP3: 4.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 330.21949481
• Heavy Atom Count: 24
• Complexity: 594

Purity/Quality:

99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OC1CCC2C1(CCC3C2CCC4C3(C=CC(=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(C=CC(=O)C4)C)C

Technology Process of 17-beta-Hydroxy-5alpha-androst-1-en-3-one acetate

There total 22 articles about 17-beta-Hydroxy-5alpha-androst-1-en-3-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: 99.6%

(5S,8R,9S,10S,13S,14S,17S)-2-bromo-10,13-dimethyl-3-oxohexadecahydro-1H-cyclopenta[a]phenanthren-17-yl acetate (952222-37-6) → (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)

Guidance literature:

With lithium carbonate; lithium bromide; In N,N-dimethyl-formamide; for 0.5h; Heating;

DOI:10.1016/j.steroids.2006.09.008

Reference yield: 72.0%

17β-acetoxy-1α-[4'-phenyl-1'H-1',2',3'-triazol-1'-yl]-5α-androstan-3β-ol (1350714-23-6) → 17β-acetoxy-1α-[4'-phenyl-1'H-1',2',3'-triazol-1'-yl]-5α-androstan-3-one (1350714-32-7) + (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)

Guidance literature:

With Jones reagent; In acetone; at 20 ℃; for 0.333333h;

DOI:10.1039/c1ob06086d

Reference yield: 67.0%

Acetic acid (2R,5S,8R,9S,10S,13S,14S,17S)-2-iodo-10,13-dimethyl-3-oxo-hexadecahydro-cyclopenta[a]phenanthren-17-yl ester → stanolone acetate (1164-91-6) + (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)

Guidance literature:

In hexane; at 20 ℃; for 4h; Irradiation;

DOI:10.1016/S0040-4039(99)02010-9

upstream raw materials:

3-Trimethylsiloxy-5α-androst-2-en-17β-ylacetat

1α-phenylthio-17β-acetoxy-5α-androstan-3-one

1α-(2-iodophenylthio)-17β-acetoxy-5α-androstan-3-one

17α-Acetoxy-5α-androst-1-en-3α-ol

Downstream raw materials:

17β-acetyloxy-1α-methyl-5α-androstan-3-one

stanolone acetate

1α-(2-iodophenylthio)-17β-acetoxy-5α-androstan-3-one

1α-phenylthio-17β-acetoxy-5α-androstan-3-one

Refernces

• 1、 Kadar, Zalan,Baji, Adam,Zupko, Istvan,Bartok, Tibor,Woelfling, Janos,Frank, Eva. "Efficient approach to novel 1α-triazolyl-5α-androstane derivatives as potent antiproliferative agents". supporting information; experimental part. p. 8051 - 8057. Retrieved 2012/01/04.
• 2、 Ji, Shun-Jun,Takahashi, Eiji,Takahashi, T. Tomoyoshi,Horiuchi, C. Akira. "Synthesis of α,β-unsaturated ketone from α-iodo ketone using photoirradiation". . p. 9263 - 9266. Retrieved 2007/10/03.