4,7-methano-1H-isoindole-1,3(2H)-dione, 3a,4,7,7a-tetrahydro-2-(2-methylphenyl)-, (3aR,4S,7R,7aS)-

Base Information

• Chemical Name: 4,7-methano-1H-isoindole-1,3(2H)-dione, 3a,4,7,7a-tetrahydro-2-(2-methylphenyl)-, (3aR,4S,7R,7aS)-
• CAS No.: 66428-16-8
• Molecular Formula: C₁₆H₁₅NO₂
• Molecular Weight: 253.301

Synonyms:(3aR,4S,7R,7aS)-2-(o-tolyl)-3a,4,7,7a-tetrahydro-1H-4,7-methanoisoindole-1,3(2H)-dione

Chemical Property of 4,7-methano-1H-isoindole-1,3(2H)-dione, 3a,4,7,7a-tetrahydro-2-(2-methylphenyl)-, (3aR,4S,7R,7aS)-

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C

Purity/Quality:

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Technology Process of 4,7-methano-1H-isoindole-1,3(2H)-dione, 3a,4,7,7a-tetrahydro-2-(2-methylphenyl)-, (3aR,4S,7R,7aS)-

There total 2 articles about 4,7-methano-1H-isoindole-1,3(2H)-dione, 3a,4,7,7a-tetrahydro-2-(2-methylphenyl)-, (3aR,4S,7R,7aS)- 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: 62.0%

5-norbornene-2,3-dicarboxylic anhydride (826-62-0,85081-15-8,85081-16-9) + o-toluidine (95-53-4) → (3aR,4S,7R,7aS)-2-(o-tolyl)-3a,4,7,7a-tetrahydro-1H-4,7-methanoisoindole-1,3(2H)-dione (66428-16-8)

Guidance literature:

In acetic acid; for 24h; Reflux;

DOI:10.1021/ja305788p

Reference yield: 41.0%

o-toluidine (95-53-4) + 3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride (129-64-6) → (3aR,4S,7R,7aS)-2-(o-tolyl)-3a,4,7,7a-tetrahydro-1H-4,7-methanoisoindole-1,3(2H)-dione (66428-16-8)

Guidance literature:

o-toluidine; 3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride; In acetonitrile; for 1h; Reflux;

With sodium acetate; acetic anhydride; at 100 ℃; for 0.5h;

DOI:10.1002/anie.201700520

Reference yield:

(3aR,4S,7R,7aS)-2-(o-tolyl)-3a,4,7,7a-tetrahydro-1H-4,7-methanoisoindole-1,3(2H)-dione (66428-16-8) → (1R,2R,6S,7S,8S,9R)-8,9-Dihydroxy-4-o-tolyl-4-aza-tricyclo[5.2.1.02,6]decane-3,5-dione

Guidance literature:

With osmium(VIII) oxide;

DOI:10.1002/(SICI)1097-458X(199904)37:4<317::AID-MRC444>3.0.CO;2-7

upstream raw materials:

o-toluidine

3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride

5-norbornene-2,3-dicarboxylic anhydride

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