11beta-(4-hydroxyphenyl)-estra-4,9-diene-3,17-dione

Base Information

• Chemical Name: 11beta-(4-hydroxyphenyl)-estra-4,9-diene-3,17-dione
• CAS No.: 134414-14-5
• Molecular Formula: C₂₄H₂₆O₃
• Molecular Weight: 362.469
• Mol file: 134414-14-5.mol

Synonyms:11beta-(4-hydroxyphenyl)-estra-4,9-diene-3,17-dione

Chemical Property of 11beta-(4-hydroxyphenyl)-estra-4,9-diene-3,17-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 11beta-(4-hydroxyphenyl)-estra-4,9-diene-3,17-dione

There total 13 articles about 11beta-(4-hydroxyphenyl)-estra-4,9-diene-3,17-dione 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: 98.0%

(4-bromophenoxy)trimethylsilane (17878-44-3) + (5'R,10'R,13'S)-13'-methyl-1',2',6',7',8',12',13',14',15',16'-decahydro-17'H-spiro[1,3-dioxolane-2,3'-[5,10]epoxycyclopenta[a]phenanthren]-17'-one (39931-88-9,116003-08-8,39931-87-8) → 11beta-(4-hydroxyphenyl)-estra-4,9-diene-3,17-dione (134414-14-5)

Guidance literature:

(4-bromophenoxy)trimethylsilane; With iodine; magnesium; In tetrahydrofuran; at 65 ℃; Inert atmosphere;

(5'R,10'R,13'S)-13'-methyl-1',2',6',7',8',12',13',14',15',16'-decahydro-17'H-spiro[1,3-dioxolane-2,3'-[5,10]epoxycyclopenta[a]phenanthren]-17'-one; With copper(l) iodide; In tetrahydrofuran; at -10 - 23 ℃; for 12h; Inert atmosphere;

With water; acetic acid; at 50 - 60 ℃; for 1.5h; Inert atmosphere;

DOI:10.1016/j.bmcl.2011.12.091

Reference yield: 90.4%

3,3,17,17-di(ethylenedioxy)-5,10-epoxy-estr-9(11)-ene (55180-24-0,130273-69-7) + 4-((trimethylsilyl)oxy)phenyl magnesium bromide (17878-42-1) → 11beta-(4-hydroxyphenyl)-estra-4,9-diene-3,17-dione (134414-14-5)

Guidance literature:

3,3,17,17-di(ethylenedioxy)-5,10-epoxy-estr-9⁽¹¹⁾-ene; 4-((trimethylsilyl)oxy)phenyl magnesium bromide; copper(l) chloride; In tetrahydrofuran; at 20 ℃; for 1.5h; Inert atmosphere;

With hydrogenchloride; water; In dichloromethane; at 0 - 5 ℃; for 2h; pH=< 1;

Reference yield: 86.0%

(5'R,10'R,13'S)-13'-methyl-1',2',6',7',8',12',13',14',15',16'-decahydro-17'H-spiro[1,3-dioxolane-2,3'-[5,10]epoxycyclopenta[a]phenanthren]-17'-one (39931-88-9,116003-08-8,39931-87-8) + 4-((trimethylsilyl)oxy)phenyl magnesium bromide (17878-42-1) → 11beta-(4-hydroxyphenyl)-estra-4,9-diene-3,17-dione (134414-14-5)

Guidance literature:

(5'R,10'R,13'S)-13'-methyl-1',2',6',7',8',12',13',14',15',16'-decahydro-17'H-spiro[1,3-dioxolane-2,3'-[5,10]epoxycyclopenta[a]phenanthren]-17'-one; 4-((trimethylsilyl)oxy)phenyl magnesium bromide; With copper(l) iodide; In tetrahydrofuran; at -10 - 20 ℃; for 16h; Inert atmosphere;

With acetic acid; In water; at 50 - 60 ℃; for 1.5h;

DOI:10.1016/j.bmcl.2013.03.116

upstream raw materials:

3,3-ethylenedioxy-5α-hydroxy-11β-[4-(2-tetrahydro-2-H-pyranoxy)-phenyl]-estr-9-en-17-one

3,3,17,17-di(ethylenedioxy)-5,10-epoxy-estr-9⁽¹¹⁾-ene

4-((trimethylsilyl)oxy)phenyl magnesium bromide

(4-bromophenoxy)trimethylsilane

Downstream raw materials:

C₃₀H₃₅NO₃

11β-[4-(2-tosyloxyethoxy)-phenyl]-estra-4,9-diene-3,17-dione

C₄₀H₅₂N₅O₅

C₃₈H₅₂N₅O₄