(3S,13S,14S)-3-hydroxy-13-methyl-2,3,4,11,12,14,15,16-octahydro-1H-cyclopenta[a]phenanthren-17-one

Base Information

• Chemical Name: (3S,13S,14S)-3-hydroxy-13-methyl-2,3,4,11,12,14,15,16-octahydro-1H-cyclopenta[a]phenanthren-17-one
• CAS No.: 567-12-4
• Molecular Formula: C18H22O2
• Molecular Weight: 270.37
• DSSTox Substance ID: DTXSID601281792
• Nikkaji Number: J6.521H
• Mol file: 567-12-4.mol

Synonyms:567-12-4;(3S,13S,14S)-3-hydroxy-13-methyl-2,3,4,11,12,14,15,16-octahydro-1H-cyclopenta[a]phenanthren-17-one;SCHEMBL6741011;OMDIWOLGOMWKEH-IWEFOYFVSA-N;DTXSID601281792;5,6,8-Estratrien-3beta-ol-17-one;(3beta)-3-Hydroxyestra-5,7,9-trien-17-one

Chemical Property of (3S,13S,14S)-3-hydroxy-13-methyl-2,3,4,11,12,14,15,16-octahydro-1H-cyclopenta[a]phenanthren-17-one

Chemical Property:

• PSA: 37.30000
• LogP: 2.93520
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 270.161979940
• Heavy Atom Count: 20
• Complexity: 418

Purity/Quality:

3β-Hydroxyestra-5,7,9-trien-17-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCC3=C(C1CCC2=O)C=CC4=C3CCC(C4)O
• Isomeric SMILES: C[C@]12CCC3=C([C@@H]1CCC2=O)C=CC4=C3CC[C@@H](C4)O
• Uses: 3β-Hydroxyestra-5,7,9-trien-17-one is a steroidal compound that is used as a reagent to synthesize 17α-derivatives of Estradiol (E888000). Estradiol is a biologically potent sex hormone that is naturally synthesized in the body. Estradiol is also suspected to be a factor in the progression of breast cancer in women.

Technology Process of (3S,13S,14S)-3-hydroxy-13-methyl-2,3,4,11,12,14,15,16-octahydro-1H-cyclopenta[a]phenanthren-17-one

There total 12 articles about (3S,13S,14S)-3-hydroxy-13-methyl-2,3,4,11,12,14,15,16-octahydro-1H-cyclopenta[a]phenanthren-17-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:

3β-acetoxy-estra-5,7,9-trien-17-one (5982-49-0) → 3β-Hydroxy-5(10),6,8-oestratrien-17-on (567-12-4)

Guidance literature:

With potassium carbonate; In methanol;

DOI:10.1135/cccc19741905

Reference yield:

3β-acetoxy-19,23,24-trinor-chola-5,7,9-trien-22-al (54024-28-1) → 3β-Hydroxy-5(10),6,8-oestratrien-17-on (567-12-4)

Guidance literature:

Multi-step reaction with 8 steps

1: aq. H₂O₂, HCO₂H / CHCl₃

2: aq. HCl / CHCl₃; methanol

3: CrO₃, aq. H₂SO₄ / acetone

4: TsOH

5: (i) monoperoxyphthalic acid, Et₂O, benzene, (ii) aq. NaOH, MeOH

6: Li / tetrahydrofuran

7: Pb(OAc)4 / acetic acid

8: aq. K₂CO₃ / methanol

With chromium(VI) oxide; lead(IV) acetate; hydrogenchloride; formic acid; sulfuric acid; dihydrogen peroxide; potassium carbonate; toluene-4-sulfonic acid; lithium tri-t-butoxyaluminum hydride; In tetrahydrofuran; methanol; chloroform; acetic acid; acetone;

DOI:10.1135/cccc19741905

Reference yield:

Acetic acid (3S,13S,14R,17S)-17-((S)-1-hydroxy-ethyl)-13-methyl-2,3,4,11,12,13,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-yl ester (54024-34-9) → 3β-Hydroxy-5(10),6,8-oestratrien-17-on (567-12-4)

Guidance literature:

Multi-step reaction with 6 steps

1: CrO₃, aq. H₂SO₄ / acetone

2: TsOH

3: (i) monoperoxyphthalic acid, Et₂O, benzene, (ii) aq. NaOH, MeOH

4: Li / tetrahydrofuran

5: Pb(OAc)4 / acetic acid

6: aq. K₂CO₃ / methanol

With chromium(VI) oxide; lead(IV) acetate; sulfuric acid; potassium carbonate; toluene-4-sulfonic acid; lithium tri-t-butoxyaluminum hydride; In tetrahydrofuran; methanol; acetic acid; acetone;

DOI:10.1135/cccc19741905

upstream raw materials:

3β-acetoxy-estra-5,7,9-trien-17-one

3β-acetoxy-19,23,24-trinor-chola-5,7,9-trien-22-al

Acetic acid (3S,13S,14R,17S)-17-((S)-1-hydroxy-ethyl)-13-methyl-2,3,4,11,12,13,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-yl ester

Acetic acid (3S,13S,14S,17R)-17-hydroxy-17-(1-hydroxy-ethyl)-13-methyl-2,3,4,11,12,13,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-yl ester

Refernces