11-methoxy-16-fluoroestradiol

Base Information

• Chemical Name: 11-methoxy-16-fluoroestradiol
• CAS No.: 129000-37-9
• Molecular Formula: C₁₉H₂₅FO₃
• Molecular Weight: 320.404
• Mol file: 129000-37-9.mol

Synonyms:16α-fluoro-11β-methoxyestra-1,3,5(10)-triene-3,17β-diol;(8S,9S,11S,13S,14S,16R,17R)-16-Fluoro-11-methoxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene-3,17-diol;16α-fluoro-11β-methoxyestradiol;

Chemical Property of 11-methoxy-16-fluoroestradiol

Chemical Property:

• Vapor Pressure: 8.99E-10mmHg at 25°C
• Boiling Point: 473.5°Cat760mmHg
• Flash Point: 207.9°C
• PSA: 49.69000
• Density: 1.25g/cm³
• LogP: 3.18210

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 11-methoxy-16-fluoroestradiol

There total 7 articles about 11-methoxy-16-fluoroestradiol 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: 55.0%

16α-fluoro-3-<<(trifluoromethyl)sulfonyl>oxy>-11β-methoxyestra-1,3,5(10)-trien-17-one (129000-52-8) → 16α-fluoro-11β-methoxyestra-1,3,5(10)-triene-3,17α-diol (129000-54-0) + 16α-fluoro-11β-methoxyestra-1,3,5(10)-triene-3,17β-diol (129000-37-9)

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether; 1.) -78 deg C, 10 min, 2.) from -78 deg C to RT, 10 min;

DOI:10.1021/jm00174a009

Reference yield:

11β-methoxyestrone (21375-11-1) → 16α-fluoro-11β-methoxyestra-1,3,5(10)-triene-3,17β-diol (129000-37-9)

Guidance literature:

Multi-step reaction with 7 steps

1: 88 percent / 2,6-lutidine / CH₂Cl₂ / 0.33 h / 0 °C

2: 41 percent / p-toluenesulfonic acid / 1.) a.) reflux, 4 h, b.) RT, 11 h, 2.) reflux, 8 h

3: 94 percent / acetonitrile; CH₂Cl₂ / 12 h / Ambient temperature

4: 91 percent / 10percent aq. EtOH / tetrahydrofuran / 12 h / Ambient temperature

5: 68 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

6: 42 percent / nBu₄NF / tetrahydrofuran / 0.5 h / Ambient temperature

7: 55 percent / LiAlH₄ / diethyl ether / 1.) -78 deg C, 10 min, 2.) from -78 deg C to RT, 10 min

With 2,6-dimethylpyridine; lithium aluminium tetrahydride; ethanol; tetrabutyl ammonium fluoride; toluene-4-sulfonic acid; In tetrahydrofuran; diethyl ether; dichloromethane; acetonitrile;

DOI:10.1021/jm00174a009

Reference yield:

3-<<(trifluoromethyl)sulfonyl>oxy>-11β-methoxyestra-1,3,5(10)-trien-17-one (129000-42-6) → 16α-fluoro-11β-methoxyestra-1,3,5(10)-triene-3,17β-diol (129000-37-9)

Guidance literature:

Multi-step reaction with 6 steps

1: 41 percent / p-toluenesulfonic acid / 1.) a.) reflux, 4 h, b.) RT, 11 h, 2.) reflux, 8 h

2: 94 percent / acetonitrile; CH₂Cl₂ / 12 h / Ambient temperature

3: 91 percent / 10percent aq. EtOH / tetrahydrofuran / 12 h / Ambient temperature

4: 68 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

5: 42 percent / nBu₄NF / tetrahydrofuran / 0.5 h / Ambient temperature

6: 55 percent / LiAlH₄ / diethyl ether / 1.) -78 deg C, 10 min, 2.) from -78 deg C to RT, 10 min

With 2,6-dimethylpyridine; lithium aluminium tetrahydride; ethanol; tetrabutyl ammonium fluoride; toluene-4-sulfonic acid; In tetrahydrofuran; diethyl ether; dichloromethane; acetonitrile;

DOI:10.1021/jm00174a009

upstream raw materials:

16α-fluoro-3-<<(trifluoromethyl)sulfonyl>oxy>-11β-methoxyestra-1,3,5(10)-trien-17-one

11β-methoxyestrone

3-<<(trifluoromethyl)sulfonyl>oxy>-11β-methoxyestra-1,3,5(10)-trien-17-one

3-<<(trifluoromethyl)sulfonyl>oxy>-16β-hydroxy-11β-methoxyestra-1,3,5(10)-trien-17-one

Refernces