(3aR,4R,11aS,11bR)-4-Amino-7-hydroxy-11a-phenyl-2,3,3a,4,5,11,11a,11b-octahydro-1H-9b-aza-benzo[cd]fluoranthen-10-one

Base Information

• Chemical Name: (3aR,4R,11aS,11bR)-4-Amino-7-hydroxy-11a-phenyl-2,3,3a,4,5,11,11a,11b-octahydro-1H-9b-aza-benzo[cd]fluoranthen-10-one
• CAS No.: 103558-81-2
• Molecular Formula: C₂₄H₂₄N₂O₂
• Molecular Weight: 372.467
• Mol file: 103558-81-2.mol

Synonyms:(3aR,4R,11aS,11bR)-4-Amino-7-hydroxy-11a-phenyl-2,3,3a,4,5,11,11a,11b-octahydro-1H-9b-aza-benzo[cd]fluoranthen-10-one

Chemical Property of (3aR,4R,11aS,11bR)-4-Amino-7-hydroxy-11a-phenyl-2,3,3a,4,5,11,11a,11b-octahydro-1H-9b-aza-benzo[cd]fluoranthen-10-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aR,4R,11aS,11bR)-4-Amino-7-hydroxy-11a-phenyl-2,3,3a,4,5,11,11a,11b-octahydro-1H-9b-aza-benzo[cd]fluoranthen-10-one

There total 10 articles about (3aR,4R,11aS,11bR)-4-Amino-7-hydroxy-11a-phenyl-2,3,3a,4,5,11,11a,11b-octahydro-1H-9b-aza-benzo[cd]fluoranthen-10-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:

((3aR,4R,11aS,11bR)-7-Benzyloxy-10-oxo-11a-phenyl-1,2,3,3a,4,5,10,11,11a,11b-decahydro-9b-aza-benzo[cd]fluoranthen-4-yl)-carbamic acid benzyl ester (103558-80-1) → (3aR,4R,11aS,11bR)-4-Amino-7-hydroxy-11a-phenyl-2,3,3a,4,5,11,11a,11b-octahydro-1H-9b-aza-benzo[cd]fluoranthen-10-one (103558-81-2)

Guidance literature:

With hydrogen; palladium on activated charcoal; In N,N-dimethyl-formamide; under 760 Torr; Ambient temperature;

DOI:10.1021/jm00083a004

Reference yield:

(1-Phenyl-cyclohex-2-enyl)-acetyl chloride (111872-78-7) → (3aR,4R,11aS,11bR)-4-Amino-7-hydroxy-11a-phenyl-2,3,3a,4,5,11,11a,11b-octahydro-1H-9b-aza-benzo[cd]fluoranthen-10-one (103558-81-2)

Guidance literature:

Multi-step reaction with 8 steps

1: 1.) NaH / 1.) DMF, RT, 30 min, 2.) DMF, 0.5 h

2: 2.) 15percent ethanol. HCl / 1.) mesitylene, reflux, 12 h, 2.) mesitylene, reflux, 0.5 h

3: tetrakis(triphenylphosphine)palladium⁽⁰⁾, Ph₃P, 2-ethylhexanoic acid / ethyl acetate; CHCl₃ / 8 h / Ambient temperature

4: ethyl chloroformate, Et₃N / acetone / 0.5 h

5: NaN₃ / acetone; H₂O / 0.5 h / 0 °C

6: xylene / 0.5 h / Heating

7: xylene / 1 h / Heating

8: H₂ / 10percent Pd/C / dimethylformamide / 760 Torr / Ambient temperature

With hydrogenchloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium azide; 2-Ethylhexanoic acid; hydrogen; chloroformic acid ethyl ester; sodium hydride; triethylamine; triphenylphosphine; palladium on activated charcoal; In chloroform; water; ethyl acetate; N,N-dimethyl-formamide; acetone; xylene;

DOI:10.1021/jm00083a004

Reference yield:

methyl (E)-3-<5-(benzyloxy)-1H-indol-3-yl>-2-propenoate (103581-94-8) → (3aR,4R,11aS,11bR)-4-Amino-7-hydroxy-11a-phenyl-2,3,3a,4,5,11,11a,11b-octahydro-1H-9b-aza-benzo[cd]fluoranthen-10-one (103558-81-2)

Guidance literature:

Multi-step reaction with 9 steps

1: 75.1 percent / toluene / 20 h / Heating

2: 1.) NaH / 1.) DMF, RT, 30 min, 2.) DMF, 0.5 h

3: 2.) 15percent ethanol. HCl / 1.) mesitylene, reflux, 12 h, 2.) mesitylene, reflux, 0.5 h

4: tetrakis(triphenylphosphine)palladium⁽⁰⁾, Ph₃P, 2-ethylhexanoic acid / ethyl acetate; CHCl₃ / 8 h / Ambient temperature

5: ethyl chloroformate, Et₃N / acetone / 0.5 h

6: NaN₃ / acetone; H₂O / 0.5 h / 0 °C

7: xylene / 0.5 h / Heating

8: xylene / 1 h / Heating

9: H₂ / 10percent Pd/C / dimethylformamide / 760 Torr / Ambient temperature

With hydrogenchloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium azide; 2-Ethylhexanoic acid; hydrogen; chloroformic acid ethyl ester; sodium hydride; triethylamine; triphenylphosphine; palladium on activated charcoal; In chloroform; water; ethyl acetate; N,N-dimethyl-formamide; acetone; toluene; xylene;

DOI:10.1021/jm00083a004

upstream raw materials:

((3aR,4R,11aS,11bR)-7-Benzyloxy-10-oxo-11a-phenyl-1,2,3,3a,4,5,10,11,11a,11b-decahydro-9b-aza-benzo[cd]fluoranthen-4-yl)-carbamic acid benzyl ester

(1-Phenyl-cyclohex-2-enyl)-acetyl chloride

methyl (E)-3-<5-(benzyloxy)-1H-indol-3-yl>-2-propenoate

allyl (E)-3-<5-(benzyloxy)-1H-indol-3-yl>-2-propenoate