17beta-Hydroxy-1alpha-methyl-5-alphaandrostan-3-one acetate

Base Information

• Chemical Name: 17beta-Hydroxy-1alpha-methyl-5-alphaandrostan-3-one acetate
• CAS No.: 4062-46-8
• Molecular Formula: C22H34 O3
• Molecular Weight: 346.51
• European Community (EC) Number: 223-768-0
• NSC Number: 75053
• DSSTox Substance ID: DTXSID001204788
• Nikkaji Number: J217.870B
• Wikidata: Q76009925
• Mol file: 4062-46-8.mol

Synonyms:4062-46-8;EINECS 223-768-0;17beta-Hydroxy-1alpha-methyl-5-alphaandrostan-3-one acetate;EC 223-768-0;NSC75053;SCHEMBL8337176;DTXSID001204788;NSC 75053;NSC-75053;17beta-Acetoxy-1alpha-methyl-5alpha-androstan-3-one;1alpha-Methyl-3-oxo-5alpha-androstan-17beta-ol acetate;(1alpha,5alpha,17beta)-17-(Acetyloxy)-1-methylandrostan-3-one

Chemical Property of 17beta-Hydroxy-1alpha-methyl-5-alphaandrostan-3-one acetate

Chemical Property:

• Boiling Point: 432.6°Cat760mmHg
• Flash Point: 185.4°C
• PSA: 43.37000
• Density: 1.08g/cm³
• LogP: 4.77590
• XLogP3: 4.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 346.25079494
• Heavy Atom Count: 25
• Complexity: 584

Purity/Quality:

99.9% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CC(=O)CC2C1(C3CCC4(C(C3CC2)CCC4OC(=O)C)C)C
• Isomeric SMILES: C[C@H]1CC(=O)C[C@H]2[C@]1([C@H]3CC[C@]4([C@H]([C@@H]3CC2)CC[C@@H]4OC(=O)C)C)C

Technology Process of 17beta-Hydroxy-1alpha-methyl-5-alphaandrostan-3-one acetate

There total 6 articles about 17beta-Hydroxy-1alpha-methyl-5-alphaandrostan-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: 93.0%

C24H38O4 → 17β-acetyloxy-1α-methyl-5α-androstan-3-one (4062-46-8)

Guidance literature:

With sulfuric acid; In tetrahydrofuran; at 22 ℃; for 6h;

DOI:10.1016/S0040-4039(00)97016-3

Reference yield: 90.0%

(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) + trimethylaluminum (75-24-1) → 17β-acetyloxy-1α-methyl-5α-androstan-3-one (4062-46-8)

Guidance literature:

With copper(I) bromide; In ethyl acetate; for 0.5h; Ambient temperature;

Reference yield:

C24H36O4 (132532-79-7) → 17β-acetyloxy-1α-methyl-5α-androstan-3-one (4062-46-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 91 percent / H₂ / ethanol; tetrahydrofuran / 22 °C

2: 93 percent / aq. H₂SO₄ / tetrahydrofuran / 6 h / 22 °C

With sulfuric acid; hydrogen; In tetrahydrofuran; ethanol;

DOI:10.1016/S0040-4039(00)97016-3

upstream raw materials:

(5α,17β)-3-oxoandrost-1-en-17-yl acetate

trimethylaluminum

C₂₄H₃₆O₄

Downstream raw materials:

atamestane

Refernces

• 1、 Westermann, Juergen,Nickisch, Klaus. "Kupferkatalysierte 1,4-Additionen von Trialkylaluminiumverbindungen an Enone". . p. 1429 - 1431. Retrieved 2007/10/02.