(1R,2S,6R,7S)-10,10-Diethoxy-4-phenyl-4-aza-tricyclo[5.2.1.0^2,6]dec-8-ene-3,5-dione

Base Information

• Chemical Name: (1R,2S,6R,7S)-10,10-Diethoxy-4-phenyl-4-aza-tricyclo[5.2.1.0^2,6]dec-8-ene-3,5-dione
• CAS No.: 79681-23-5
• Molecular Formula: C₁₉H₂₁NO₄
• Molecular Weight: 327.38

Synonyms:(1R,2S,6R,7S)-10,10-Diethoxy-4-phenyl-4-aza-tricyclo[5.2.1.0^2,6]dec-8-ene-3,5-dione

Chemical Property of (1R,2S,6R,7S)-10,10-Diethoxy-4-phenyl-4-aza-tricyclo[5.2.1.0^2,6]dec-8-ene-3,5-dione

Chemical Property:

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Technology Process of (1R,2S,6R,7S)-10,10-Diethoxy-4-phenyl-4-aza-tricyclo[5.2.1.0^2,6]dec-8-ene-3,5-dione

There total 1 articles about (1R,2S,6R,7S)-10,10-Diethoxy-4-phenyl-4-aza-tricyclo[5.2.1.0^2,6]dec-8-ene-3,5-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: 54.0%

N-phenyl-maleimide (941-69-5) + cyclopentadienone-diethyl ketal (2931-32-0) → (1R,2S,6R,7S)-10,10-Diethoxy-4-phenyl-4-aza-tricyclo[5.2.1.02,6]dec-8-ene-3,5-dione (79681-23-5)

Guidance literature:

In Petroleum ether; for 2h;

DOI:10.1021/jo00340a014

Reference yield: 30.0%

(1R,2S,6R,7S)-10,10-Diethoxy-4-phenyl-4-aza-tricyclo[5.2.1.02,6]dec-8-ene-3,5-dione (79681-23-5) + 1,3-dibromo-propane (109-64-8) → (3aR,4R,7S,7aS)-11,11-diethoxy-2-phenyl-1H,3H-4,7-methano-3a,7a-propanoisoindol-1,3-dione (79681-24-6)

Guidance literature:

With naphthalene; lithium; isopropylamine; In tetrahydrofuran; 1.) -78 deg C, 45 min, 2.) 0 deg C, 1 h;

Reference yield:

(1R,2S,6R,7S)-10,10-Diethoxy-4-phenyl-4-aza-tricyclo[5.2.1.02,6]dec-8-ene-3,5-dione (79681-23-5) → meso-(3aR,4S,7R,7aS)-5,6-dihydro-2-phenyl-1H,3H-4,7-methano-3a,7a-propanoisoindol-1,3,11-trione (93248-39-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 97 percent / H₂ / 10percent Pd/C / ethyl acetate / 82 h / 3192 Torr

2: 40 percent / 1.) Li, isopropylamine, naphthalene / tetrahydrofuran / 1.) -78 deg C, 45 min, 2.) 0 deg C, 1 h

3: 95 percent / 15percent aq. HClO₄ / 12 h / Heating

With perchloric acid; naphthalene; hydrogen; lithium; isopropylamine; palladium on activated charcoal; In tetrahydrofuran; ethyl acetate;

upstream raw materials:

N-phenyl-maleimide

cyclopentadienone-diethyl ketal

Downstream raw materials:

(3aR,4R,7S,7aS)-11,11-diethoxy-2-phenyl-1H,3H-4,7-methano-3a,7a-propanoisoindol-1,3-dione

meso-(3aR,4S,7R,7aS)-5,6-dihydro-2-phenyl-1H,3H-4,7-methano-3a,7a-propanoisoindol-1,3,11-trione

meso-(3aR,4S,7R,7aS)-11,11-diethoxy-5,6-dihydro-2-phenyl-1H,3H-4,7-methano-3a,7a-propanoisoindol-1,3-dione

meso-(3aR,4R,7S,7aS)-11,11-diethoxy-5,6-dihydro-2-phenyl-1H,3H-4,7-methano-3a,7a-propanoisoindol-1,3-dione

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