(1beta,4beta)-N-Phenyl-7-oxabicyclo[2.2.1]hepta-5-ene-2beta,3beta-dicarbimide

Base Information

• Chemical Name: (1beta,4beta)-N-Phenyl-7-oxabicyclo[2.2.1]hepta-5-ene-2beta,3beta-dicarbimide
• CAS No.: 10039-57-3
• Molecular Formula: C₁₄H₁₁NO₃
• Molecular Weight: 241.246
• DSSTox Substance ID: DTXSID401126384
• Nikkaji Number: J1.285.571K
• Mol file: 10039-57-3.mol

Synonyms:DTXSID401126384;10039-57-3;(1beta,4beta)-N-Phenyl-7-oxabicyclo[2.2.1]hepta-5-ene-2beta,3beta-dicarbimide;rel-(3aR,4S,7R,7aS)-3a,4,7,7a-Tetrahydro-2-phenyl-4,7-epoxy-1H-isoindole-1,3(2H)-dione

Chemical Property of (1beta,4beta)-N-Phenyl-7-oxabicyclo[2.2.1]hepta-5-ene-2beta,3beta-dicarbimide

Chemical Property:

• XLogP3: 0.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 241.07389321
• Heavy Atom Count: 18
• Complexity: 408

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=CC=C(C=C1)N2C(=O)C3C4C=CC(C3C2=O)O4
• Isomeric SMILES: C1=CC=C(C=C1)N2C(=O)[C@@H]3[C@H]4C=C[C@@H]([C@@H]3C2=O)O4

Technology Process of (1beta,4beta)-N-Phenyl-7-oxabicyclo[2.2.1]hepta-5-ene-2beta,3beta-dicarbimide

There total 8 articles about (1beta,4beta)-N-Phenyl-7-oxabicyclo[2.2.1]hepta-5-ene-2beta,3beta-dicarbimide 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: 84.0%

furan (110-00-9) + N-phenyl-maleimide (941-69-5) → (+/-)-(3aR,4S,7R,7aS)-2-phenyl-3a,4,7,7a-tetrahydro-1H-4,7-epoxyisoindole-1,3(2H)-dione (10039-57-3)

Guidance literature:

In acetonitrile; for 5h; Reflux; Inert atmosphere;

DOI:10.1002/adsc.201500971

Reference yield: 68.8%

exo-3,6-epoxy-1,2,3,6-tetrahydrophthalic anhydride (6118-51-0) + aniline (62-53-3) → (+/-)-(3aR,4S,7R,7aS)-2-phenyl-3a,4,7,7a-tetrahydro-1H-4,7-epoxyisoindole-1,3(2H)-dione (10039-57-3)

Guidance literature:

exo-3,6-epoxy-1,2,3,6-tetrahydrophthalic anhydride; aniline; In acetone; at 20 ℃; for 1h;

With (AcO)2O; manganese(II) acetate; triethylamine; In acetone; at 50 - 60 ℃; for 2h;

DOI:10.1002/jhet.5570420103

Reference yield:

exo-3,6-epoxy-1,2,3,6-tetrahydrophthalic anhydride (6118-51-0) → (+/-)-(3aR,4S,7R,7aS)-2-phenyl-3a,4,7,7a-tetrahydro-1H-4,7-epoxyisoindole-1,3(2H)-dione (10039-57-3)

Guidance literature:

Multi-step reaction with 2 steps

1: toluene / 2 h / 40 °C

2: sodium acetate; acetic anhydride / 3 h / 70 °C

With sodium acetate; acetic anhydride; In toluene;

DOI:10.1021/ma030285a

upstream raw materials:

exo-3,6-epoxy-1,2,3,6-tetrahydrophthalic anhydride

aniline

furan

N-phenyl-maleimide