8,9-Dihydro-6H-1,3-dioxolo[4,5-k]pyrrolo[3,2,1-de]phenanthridin-6-one

Base Information

• Chemical Name: 8,9-Dihydro-6H-1,3-dioxolo[4,5-k]pyrrolo[3,2,1-de]phenanthridin-6-one
• CAS No.: 128581-38-4
• Molecular Formula: C₁₆H₁₁NO₃
• Molecular Weight: 265.268
• DSSTox Substance ID: DTXSID101156433
• Mol file: 128581-38-4.mol

Synonyms:DTXSID101156433;8,9-Dihydro-6H-1,3-dioxolo[4,5-k]pyrrolo[3,2,1-de]phenanthridin-6-one;128581-38-4

Chemical Property of 8,9-Dihydro-6H-1,3-dioxolo[4,5-k]pyrrolo[3,2,1-de]phenanthridin-6-one

Chemical Property:

• XLogP3: 2.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 265.07389321
• Heavy Atom Count: 20
• Complexity: 439

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1CN2C3=C1C=CC=C3C4=C(C2=O)C=CC5=C4OCO5

Technology Process of 8,9-Dihydro-6H-1,3-dioxolo[4,5-k]pyrrolo[3,2,1-de]phenanthridin-6-one

There total 4 articles about 8,9-Dihydro-6H-1,3-dioxolo[4,5-k]pyrrolo[3,2,1-de]phenanthridin-6-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: 55.0%

1-[(1,3-benzodioxol-5-yl)methyl]-7-iodo-2,3-dihydroindole → 4,5-dihydro-7H-[1,3]dioxolo[4,5-k]pyrrolo[3,2,1-de]phenanthridine + anhydrolycorine (641-89-4) + anhydrolycorine-7-one (40360-71-2) + 4,5-dihydro-7H-[1,3]dioxolo[4,5-k]pyrrolo[3,2,1-de]phenanthridin-7-one (128581-38-4)

Guidance literature:

With potassium carbonate; tris-(o-tolyl)phosphine; palladium diacetate; In N,N-dimethyl-formamide; at 125 ℃; for 2.5h; Further Variations:; Reagents; Temperatures; time; Product distribution;

DOI:10.3987/COM-05-S(T)5

Reference yield: 48.0%

1-[(1,3-benzodioxol-5-yl)carbonyl]-7-iodo-2,3-dihydroindole (660399-10-0) → anhydrolycorine-7-one (40360-71-2) + 4,5-dihydro-7H-[1,3]dioxolo[4,5-k]pyrrolo[3,2,1-de]phenanthridin-7-one (128581-38-4)

Guidance literature:

With N,N,N,N,N,N-hexamethylphosphoric triamide; samarium; 1,2-Diiodoethane; In tetrahydrofuran; at 0 ℃; Inert atmosphere;

DOI:10.1016/j.tet.2015.06.067

Reference yield: 12.0%

1-[(1,3-benzodioxol-5-yl)carbonyl]-7-iodo-2,3-dihydroindole (660399-10-0) → 1-[(1,3-benzodioxol-5-yl)carbonyl]-2,3-dihydroindole (40360-67-6) + anhydrolycorine-7-one (40360-71-2) + 4,5-dihydro-7H-[1,3]dioxolo[4,5-k]pyrrolo[3,2,1-de]phenanthridin-7-one (128581-38-4)

Guidance literature:

With tributylphosphine; 1,3-bis-(diphenylphosphino)propane; silver carbonate; palladium diacetate; In N,N-dimethyl-formamide; for 2h; Heating;

DOI:10.3987/COM-03-S10

upstream raw materials:

1-[(1,3-benzodioxol-5-yl)carbonyl]-2,3-dihydroindole

1-[(1,3-benzodioxol-5-yl)carbonyl]-7-iodo-2,3-dihydroindole