17-Ethynyl-9,17-dihydroxyandrost-4-en-3-one

Base Information

• Chemical Name: 17-Ethynyl-9,17-dihydroxyandrost-4-en-3-one
• CAS No.: 116256-39-4
• Molecular Formula: C21H28 O3
• Molecular Weight: 328.452
• Mol file: 116256-39-4.mol

Synonyms:17-ethynyl-9,17-dihydroxyandrost-4-en-3-one;EtdiOHandrostene-3-one

Chemical Property of 17-Ethynyl-9,17-dihydroxyandrost-4-en-3-one

Chemical Property:

• Boiling Point: 482.7°Cat760mmHg
• Flash Point: 259.8°C
• PSA: 57.53000
• Density: 1.21g/cm³
• LogP: 2.99750
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 328.20384475
• Heavy Atom Count: 24
• Complexity: 684

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCC3(C(C1CCC2(C#C)O)CCC4=CC(=O)CCC43C)O
• Isomeric SMILES: C[C@]12CC[C@]3([C@H]([C@@H]1CC[C@]2(C#C)O)CCC4=CC(=O)CC[C@@]43C)O

Technology Process of 17-Ethynyl-9,17-dihydroxyandrost-4-en-3-one

There total 5 articles about 17-Ethynyl-9,17-dihydroxyandrost-4-en-3-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:

9-alpha-hydroxyandrost-4-ene-3,17-dione (560-62-3,23015-99-8) → 9α,17β-dihydroxy-17α-ethynylandrost-4-en-3-one (116256-39-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.3 g / 5percent H₂SO₄ / methanol / 1 h / Ambient temperature

2: 0.708 g / ethylenediamine / tetrahydrofuran / 20 h / Ambient temperature

With sulfuric acid; ethylenediamine; In tetrahydrofuran; methanol;

DOI:10.1016/0039-128X(88)90002-5

Reference yield:

9α-hydroxy-3-methoxy-3,5-androstenedione-17-one (116256-30-5) → 9α,17β-dihydroxy-17α-ethynylandrost-4-en-3-one (116256-39-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 4.0 g / ethane-1,2-diamine; tetrahydrofuran / 2.5 h / Ambient temperature

2: 1) LiBr, 15percent BuLi / 1) THF, hexane, -60 deg C, 45 min, 2) THF, hexane, -60 deg C, 45 min

3: 1) AgNO₃, 2) 4 M aq. HCl / 1) THF, H₂O, 2 h, 2) MeOH, H₂O, r.t., 15 min

With hydrogenchloride; n-butyllithium; silver nitrate; lithium bromide; In tetrahydrofuran; ethylenediamine;

DOI:10.1016/0039-128X(89)90006-8

Reference yield:

9α-hydroxy-3-methoxy-3,5-androstenedione-17-one (116256-30-5) + lithium acetylide (70277-75-7) → 9α,17β-dihydroxy-17α-ethynylandrost-4-en-3-one (116256-39-4)

Guidance literature:

With ethylenediamine; In tetrahydrofuran; for 20h; Ambient temperature;

DOI:10.1016/0039-128X(88)90002-5

upstream raw materials:

17α-Ethynyl-!7β-methanesulfonyloxy-3-methoxyandrosta-3,5-diene-9α-ol

9α-hydroxy-3-methoxy-3,5-androstenedione-17-one

lithium acetylide

9-alpha-hydroxyandrost-4-ene-3,17-dione

Downstream raw materials:

17β-Ethynyl-9α,17α-dihydroxyandrost-4-en-3-one

pregna-4,9⁽¹¹⁾-diene-3,20-dione-17-hydroxy-21-methyl