pregnane-20-one

Base Information

• Chemical Name: pregnane-20-one
• CAS No.: 32695-80-0
• Molecular Formula: C₂₁H₃₄O
• Molecular Weight: 302.5
• Mol file: 32695-80-0.mol

Synonyms:Androstane,17-acetyl-

Chemical Property of pregnane-20-one

Chemical Property:

• Vapor Pressure: 2.79E-06mmHg at 25°C
• Boiling Point: 389.7°Cat760mmHg
• Flash Point: 207.1°C
• PSA: 17.07000
• Density: 0.99g/cm³
• LogP: 5.62440

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of pregnane-20-one

There total 17 articles about pregnane-20-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: 99.0%

dl-Δ1-5β-pregnen-20-one (2426-34-8,42723-55-7,42723-56-8,42723-57-9,57968-14-6,73284-89-6) → dl-5β-pregnan-20-one (848-62-4,4729-67-3,7704-90-7,32695-80-0,42723-58-0,72905-00-1)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethyl acetate; for 0.75h; Ambient temperature; atmospheric pressure;

DOI:10.1021/ja00522a060

Reference yield:

[3-(7-Methyl-1,4-dithia-spiro[4.5]dec-6-en-8-yl)-propyl]-triphenyl-phosphonium; iodide (42723-36-4,42723-37-5,43011-31-0,61690-50-4) → d-5β-pregnan-20-one (848-62-4,4729-67-3,7704-90-7,32695-80-0,42723-58-0,72905-00-1)

Guidance literature:

Multi-step reaction with 5 steps

1: phenyllithium / tetrahydrofuran

2: 41 percent / methyl iodide, water, calcium carbonate / dimethylformamide / 44 h / Ambient temperature

3: sodium bis(2-methoxyethoxy)alumino hydride / tetrahydrofuran / 1 h / 0 °C

4: ethylene carbonate, trifluoroacetic acid / various solvent(s) / 1.5 h / -25 °C

5: 2.) H₂ / 1.) deactivated Raney nickel, 2.) 10percent palladium on carbon / 1.) ethyl acetate, ethanol, room temperature, 20 min, 2.) ethyl acetate, 1 h

With [1,3]-dioxolan-2-one; water; hydrogen; phenyllithium; sodium bis(2-methoxyethoxy)aluminium dihydride; trifluoroacetic acid; calcium carbonate; methyl iodide; palladium on activated charcoal; deactivated Raney nickel; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1021/ja00521a057

Reference yield:

d-3-(2-methyl-4-oxo-2-cyclohexenyl)propanol ethylene thioketal (42723-32-0,42723-33-1,42723-34-2,79839-56-8) → d-5β-pregnan-20-one (848-62-4,4729-67-3,7704-90-7,32695-80-0,42723-58-0,72905-00-1)

Guidance literature:

Multi-step reaction with 8 steps

1: pyridine / 2 h / 0 °C

2: diisopropylethylamine, sodium iodide / acetone / 2.5 h / Ambient temperature

3: diisopropylethylamine / acetonitrile / 18 h / 50 °C

4: phenyllithium / tetrahydrofuran

5: 41 percent / methyl iodide, water, calcium carbonate / dimethylformamide / 44 h / Ambient temperature

6: sodium bis(2-methoxyethoxy)alumino hydride / tetrahydrofuran / 1 h / 0 °C

7: ethylene carbonate, trifluoroacetic acid / various solvent(s) / 1.5 h / -25 °C

8: 2.) H₂ / 1.) deactivated Raney nickel, 2.) 10percent palladium on carbon / 1.) ethyl acetate, ethanol, room temperature, 20 min, 2.) ethyl acetate, 1 h

With pyridine; [1,3]-dioxolan-2-one; water; hydrogen; phenyllithium; N-ethyl-N,N-diisopropylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; trifluoroacetic acid; calcium carbonate; sodium iodide; methyl iodide; palladium on activated charcoal; deactivated Raney nickel; In tetrahydrofuran; N,N-dimethyl-formamide; acetone; acetonitrile;

DOI:10.1021/ja00521a057

upstream raw materials:

Δ¹-5β-pregnen-20-one

dl-Δ¹-5β-pregnen-20-one

d-Δ¹-5β-pregnen-20-one

[3-(7-Methyl-1,4-dithia-spiro[4.5]dec-6-en-8-yl)-propyl]-triphenyl-phosphonium; iodide

Refernces

• 1、 Gravestock, Michael B.,Morton, Douglas R.,Boots, Sharon G.,Johnson, William S.. "Biomimetic Polyene Cyclizations. Participation of the Methylacetylenic Terminator and Nitroalkanes. A Synthesis of Testosterone". . p. 800 - 807. Retrieved 2007/10/02.