Androst-4-ene-3alpha,17alpha-diol

Base Information

• Chemical Name: Androst-4-ene-3alpha,17alpha-diol
• CAS No.: 15183-38-7
• Molecular Formula: C₁₉H₃₀O₂
• Molecular Weight: 290.446
• DSSTox Substance ID: DTXSID601311882
• Nikkaji Number: J816.395B
• Mol file: 15183-38-7.mol

Synonyms:15183-38-7;androst-4-ene-3alpha,17alpha-diol;4-ANDROSTEN-3-alpha, 17-alpha-DIOL;(3R,8R,9S,10R,13S,14S,17R)-10,13-dimethyl-2,3,6,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3,17-diol;(1R,3aS,3bR,7R,9aR,9bS,11aS)-9a,11a-dimethyl-1H,2H,3H,3aH,3bH,4H,5H,7H,8H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthrene-1,7-diol;4-androsten-3alpha,17alpha-diol;SCHEMBL2192606;BTTWKVFKBPAFDK-QAZMUZRASA-N;DTXSID601311882;delta4-Androstene-3alpha,17alpha-

Chemical Property of Androst-4-ene-3alpha,17alpha-diol

Chemical Property:

• Boiling Point: 430.1±45.0 °C(Predicted)
• PKA: 14.38±0.70(Predicted)
• Density: 1.12±0.1 g/cm3(Predicted)
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 290.224580195
• Heavy Atom Count: 21
• Complexity: 470

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC12CCC3C(C1CCC2O)CCC4=CC(CCC34C)O
• Isomeric SMILES: C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@H]2O)CCC4=C[C@@H](CC[C@]34C)O

Technology Process of Androst-4-ene-3alpha,17alpha-diol

There total 11 articles about Androst-4-ene-3alpha,17alpha-diol 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: 100.0%

testosterone (58-22-0,481-30-1,521-20-0,571-41-5,604-39-7,897-03-0,1423-92-3,4069-18-5,4593-59-3,4593-60-6,4860-75-7,28336-24-5,68833-09-0,79732-28-8,86335-11-7,90457-66-2,94991-78-3) → (10S,13R)-10,13-Dimethyl-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,17-diol (1156-92-9,1852-61-5,4223-60-3,15183-38-7,15216-04-3,16852-92-9,17218-62-1,81176-75-2,94595-22-9,111467-21-1)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; for 1h; Heating;

DOI:10.1016/0040-4020(82)85020-5

Reference yield:

4-androstane-3β,17β-diol 3,17-diacetate (4136-03-2,15129-80-3,72692-24-1,123880-21-7) → 4-androstane-3β,17β-diol (1156-92-9,1852-61-5,4223-60-3,15183-38-7,15216-04-3,16852-92-9,17218-62-1,81176-75-2,94595-22-9,111467-21-1)

Guidance literature:

With potassium hydroxide; In methanol; at 50 ℃; for 3h;

DOI:10.1135/cccc19840157

Reference yield:

4-androstane-3β,17β-diol 17-acetate (13903-65-6,16992-89-5,17320-63-7,95119-10-1) → 4-androstane-3β,17β-diol (1156-92-9,1852-61-5,4223-60-3,15183-38-7,15216-04-3,16852-92-9,17218-62-1,81176-75-2,94595-22-9,111467-21-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 187 mg / pyridine / 18 h / Ambient temperature

2: 105 mg / KOH / methanol / 3 h / 50 °C

With pyridine; potassium hydroxide; In methanol;

DOI:10.1135/cccc19840157

upstream raw materials:

4-androstane-3β,17β-diol 3,17-diacetate

4-androstane-3β,17β-diol 17-acetate

4-androstene-3,17-dione

testosterone

Downstream raw materials:

androst-3-en-3,17-dion

Refernces

• 1、 Joska,Fajkos. "Synthesis of some 1,2-unsaturated analogues of androgens with the cyclopropane ring in 4,5-position". . p. 157 - 164. Retrieved 2007/10/02.