(3aS,8aR)-6,6-Diacetyl-2-phenyl-4,5,6,7,8,8a-hexahydro-3aH-cyclopenta[f]isoindole-1,3-dione

Base Information

• Chemical Name: (3aS,8aR)-6,6-Diacetyl-2-phenyl-4,5,6,7,8,8a-hexahydro-3aH-cyclopenta[f]isoindole-1,3-dione
• CAS No.: 118453-26-2
• Molecular Formula: C₂₁H₂₁NO₄
• Molecular Weight: 351.402

Synonyms:(3aS,8aR)-6,6-Diacetyl-2-phenyl-4,5,6,7,8,8a-hexahydro-3aH-cyclopenta[f]isoindole-1,3-dione

Chemical Property of (3aS,8aR)-6,6-Diacetyl-2-phenyl-4,5,6,7,8,8a-hexahydro-3aH-cyclopenta[f]isoindole-1,3-dione

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Technology Process of (3aS,8aR)-6,6-Diacetyl-2-phenyl-4,5,6,7,8,8a-hexahydro-3aH-cyclopenta[f]isoindole-1,3-dione

There total 3 articles about (3aS,8aR)-6,6-Diacetyl-2-phenyl-4,5,6,7,8,8a-hexahydro-3aH-cyclopenta[f]isoindole-1,3-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: 87.0%

N-phenyl-maleimide (941-69-5) + 1,1'-(3,4-dimethylenecyclopentane-1,1-diyl)bis(ethan-1-one) (94935-35-0) → (3aS,8aR)-6,6-Diacetyl-2-phenyl-4,5,6,7,8,8a-hexahydro-3aH-cyclopenta[f]isoindole-1,3-dione (118453-26-2)

Guidance literature:

In chloroform; at 60 ℃; for 0.1h;

DOI:10.1016/S0040-4020(01)90346-1

Reference yield:

3-allyl-2,4-pentanedione (3508-78-9) → (3aS,8aR)-6,6-Diacetyl-2-phenyl-4,5,6,7,8,8a-hexahydro-3aH-cyclopenta[f]isoindole-1,3-dione (118453-26-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 70 percent / potassium carbonate / acetone / 22 h / Heating

2: potassium carbonate / Pd(OAc)2,PPh₃ / acetonitrile / 2.3 h / 80 °C

3: 87 percent / CHCl₃ / 0.1 h / 60 °C

With potassium carbonate; Pd(PPh₃)(OAc)2; In chloroform; acetone; acetonitrile;

DOI:10.1016/S0040-4020(01)90346-1

Reference yield:

2-bromo-4,4-diacetylhepta-1,6-diene (118453-15-9) → (3aS,8aR)-6,6-Diacetyl-2-phenyl-4,5,6,7,8,8a-hexahydro-3aH-cyclopenta[f]isoindole-1,3-dione (118453-26-2)

Guidance literature:

Multi-step reaction with 2 steps

1: potassium carbonate / Pd(OAc)2,PPh₃ / acetonitrile / 2.3 h / 80 °C

2: 87 percent / CHCl₃ / 0.1 h / 60 °C

With potassium carbonate; Pd(PPh₃)(OAc)2; In chloroform; acetonitrile;

DOI:10.1016/S0040-4020(01)90346-1

upstream raw materials:

N-phenyl-maleimide

1,1'-(3,4-dimethylenecyclopentane-1,1-diyl)bis(ethan-1-one)

3-allyl-2,4-pentanedione

2-bromo-4,4-diacetylhepta-1,6-diene

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