ent-17α-(prop-1-ynyl)-17β-hydroxy-11β-<4-(N,N-dimethylamino)-phenyl>-4,9-estradien-3-one

Base Information

• Chemical Name: ent-17α-(prop-1-ynyl)-17β-hydroxy-11β-<4-(N,N-dimethylamino)-phenyl>-4,9-estradien-3-one
• CAS No.: 101978-06-7
• Molecular Formula: C₂₉H₃₅NO₂
• Molecular Weight: 429.602
• Mol file: 101978-06-7.mol

Synonyms:ent-17α-(prop-1-ynyl)-17β-hydroxy-11β-<4-(N,N-dimethylamino)-phenyl>-4,9-estradien-3-one

Chemical Property of ent-17α-(prop-1-ynyl)-17β-hydroxy-11β-<4-(N,N-dimethylamino)-phenyl>-4,9-estradien-3-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ent-17α-(prop-1-ynyl)-17β-hydroxy-11β-<4-(N,N-dimethylamino)-phenyl>-4,9-estradien-3-one

There total 10 articles about ent-17α-(prop-1-ynyl)-17β-hydroxy-11β-<4-(N,N-dimethylamino)-phenyl>-4,9-estradien-3-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: 79.0%

ent-17α-prop-1-ynyl-11β-<4-(N,N-dimethylamino)-phenyl>-3,3-(2,2-dimethyl-trimethylene-1,3-dioxy)-estr-9-ene-5α,17β-diol (102043-75-4) → ent-17α-(prop-1-ynyl)-17β-hydroxy-11β-<4-(N,N-dimethylamino)-phenyl>-4,9-estradien-3-one (101978-06-7)

Guidance literature:

In acetic acid; at 50 ℃; for 1.5h;

DOI:10.1016/S0039-128X(84)80033-1

Reference yield:

4-bromo-N,N-dimethylaniline (586-77-6) → ent-17α-(prop-1-ynyl)-17β-hydroxy-11β-<4-(N,N-dimethylamino)-phenyl>-4,9-estradien-3-one (101978-06-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 75 percent / Mg, CuCl / tetrahydrofuran / 5 deg C to r.t.

2: 70 percent / cyclohexanone, Al isopropoxide / toluene / Heating

3: 97 percent / BuLi / tetrahydrofuran

4: 79 percent / aq. acetic acid / 1.5 h / 50 °C

With n-butyllithium; cyclohexanone; aluminum isopropoxide; magnesium; copper(l) chloride; In tetrahydrofuran; acetic acid; toluene;

DOI:10.1016/S0039-128X(84)80033-1

Reference yield:

ent-3-methoxy-1,3,5(10),9(11)-estratetraen-17α-ol (1157-01-3,6702-61-0,17287-85-3,18656-80-9,108267-88-5,113350-47-3) → ent-17α-(prop-1-ynyl)-17β-hydroxy-11β-<4-(N,N-dimethylamino)-phenyl>-4,9-estradien-3-one (101978-06-7)

Guidance literature:

Multi-step reaction with 9 steps

1: 96 percent / Li, liq. NH₃ / tetrahydrofuran

2: 97 percent / oxalic acid / acetone / 1.5 h / Ambient temperature

3: 34 percent / pyridinium bromide perbromide / pyridine / 1.5 h / 50 °C

4: 74 percent / trimethyl orthoformate, p-toluenesulfonic acid / CH₂Cl₂ / Ambient temperature

5: 47 percent / H₂O₂, hexachloroacetone, pyridine / CH₂Cl₂ / 5 deg C to r.t.

6: 75 percent / Mg, CuCl / tetrahydrofuran / 5 deg C to r.t.

7: 70 percent / cyclohexanone, Al isopropoxide / toluene / Heating

8: 97 percent / BuLi / tetrahydrofuran

9: 79 percent / aq. acetic acid / 1.5 h / 50 °C

With pyridine; n-butyllithium; 1,1,1,3,3,3-hexachloro-propan-2-one; ammonia; dihydrogen peroxide; pyridinium hydrobromide perbromide; oxalic acid; cyclohexanone; aluminum isopropoxide; lithium; toluene-4-sulfonic acid; magnesium; copper(l) chloride; trimethyl orthoformate; In tetrahydrofuran; pyridine; dichloromethane; acetic acid; acetone; toluene;

DOI:10.1016/S0039-128X(84)80033-1

upstream raw materials:

ent-17α-prop-1-ynyl-11β-<4-(N,N-dimethylamino)-phenyl>-3,3-(2,2-dimethyl-trimethylene-1,3-dioxy)-estr-9-ene-5α,17β-diol

4-bromo-N,N-dimethylaniline

ent-3-methoxy-1,3,5(10),9(11)-estratetraen-17α-ol

ent-3,3-(2,2-dimethyltrimethylen-1,3-dioxy)-5(10),9(11)-estradien-17α-ol