3,3-ethylenedioxy-5α,17β-dihydroxy-11β-[4-(methoxy)phenyl]-19-nor-17α-pregn-9-ene-21-ethyne

Base Information

• Chemical Name: 3,3-ethylenedioxy-5α,17β-dihydroxy-11β-[4-(methoxy)phenyl]-19-nor-17α-pregn-9-ene-21-ethyne
• CAS No.: 67983-34-0
• Molecular Formula: C₂₉H₃₆O₅
• Molecular Weight: 464.602
• Mol file: 67983-34-0.mol

Synonyms:3,3-ethylenedioxy-5α,17β-dihydroxy-11β-[4-(methoxy)phenyl]-19-nor-17α-pregn-9-ene-21-ethyne

Chemical Property of 3,3-ethylenedioxy-5α,17β-dihydroxy-11β-[4-(methoxy)phenyl]-19-nor-17α-pregn-9-ene-21-ethyne

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3,3-ethylenedioxy-5α,17β-dihydroxy-11β-[4-(methoxy)phenyl]-19-nor-17α-pregn-9-ene-21-ethyne

There total 7 articles about 3,3-ethylenedioxy-5α,17β-dihydroxy-11β-[4-(methoxy)phenyl]-19-nor-17α-pregn-9-ene-21-ethyne 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: 79.0%

acetylenemagnesium bromide (4301-14-8) + 3,3-ethylenedioxy-5α-hydroxy-11β-[4-(methoxy)phenyl]-estr-9-en-17-one (93678-28-5) → 3,3-ethylenedioxy-5α,17β-dihydroxy-11β-[4-(methoxy)phenyl]-19-nor-17α-pregn-9-ene-21-ethyne (67983-34-0)

Guidance literature:

In tetrahydrofuran; at 20 ℃; for 16h;

DOI:10.1016/j.steroids.2006.07.003

Reference yield:

(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) → 3,3-ethylenedioxy-5α,17β-dihydroxy-11β-[4-(methoxy)phenyl]-19-nor-17α-pregn-9-ene-21-ethyne (67983-34-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 34 percent / CuCl / tetrahydrofuran / 1 h / 20 °C

2: 79 percent / tetrahydrofuran / 16 h / 20 °C

With copper(l) chloride; In tetrahydrofuran;

DOI:10.1016/j.steroids.2006.07.003

Reference yield:

ethylene deltenone (5571-36-8) → 3,3-ethylenedioxy-5α,17β-dihydroxy-11β-[4-(methoxy)phenyl]-19-nor-17α-pregn-9-ene-21-ethyne (67983-34-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 36 percent / NaHCO₃; mCPBA / CH₂Cl₂ / 0.5 h / -40 °C

2: 34 percent / CuCl / tetrahydrofuran / 1 h / 20 °C

3: 79 percent / tetrahydrofuran / 16 h / 20 °C

With sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; copper(l) chloride; In tetrahydrofuran; dichloromethane;

DOI:10.1016/j.steroids.2006.07.003

upstream raw materials:

3,3-ethylenedioxy-5-hydroxy-11β-p-methoxyphenyl-17-trimethylsilyloxy-5α-estr-9-ene-17β-carbonitrile

lithium acetylide

acetylenemagnesium bromide

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

Downstream raw materials:

(8S,9R,11S,13S,14S,17R)-17-Ethynyl-11-(4-methoxy-phenyl)-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene-3,17-diol

11β-(p-methoxyphenyl)-17β-hydroxy-17α-ethynyl-4,9(10)-estradien-3-one