9-(4-Aminophenyl)-3,4,6,7,9,10-hexahydro-3,3,6,6-tetramethyl-1,8(2H,5H)-acridinedione

Base Information

• Chemical Name: 9-(4-Aminophenyl)-3,4,6,7,9,10-hexahydro-3,3,6,6-tetramethyl-1,8(2H,5H)-acridinedione
• CAS No.: 847658-75-7
• Molecular Formula: C23H28N2O2
• Molecular Weight: 364.488
• DSSTox Substance ID: DTXSID701127048
• Mol file: 847658-75-7.mol

Synonyms:DTXSID701127048;9-(4-Aminophenyl)-3,4,6,7,9,10-hexahydro-3,3,6,6-tetramethyl-1,8(2H,5H)-acridinedione;847658-75-7

Chemical Property of 9-(4-Aminophenyl)-3,4,6,7,9,10-hexahydro-3,3,6,6-tetramethyl-1,8(2H,5H)-acridinedione

Chemical Property:

• XLogP3: 3.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 364.215078140
• Heavy Atom Count: 27
• Complexity: 696

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1(CC2=C(C(C3=C(N2)CC(CC3=O)(C)C)C4=CC=C(C=C4)N)C(=O)C1)C

Technology Process of 9-(4-Aminophenyl)-3,4,6,7,9,10-hexahydro-3,3,6,6-tetramethyl-1,8(2H,5H)-acridinedione

There total 6 articles about 9-(4-Aminophenyl)-3,4,6,7,9,10-hexahydro-3,3,6,6-tetramethyl-1,8(2H,5H)-acridinedione 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: 70.0%

3,3,6,6-tetramethyl-9-(4-nitrophenyl)-1,8-dioxodecahydroacridine (3357-14-0) → 9-(4-aminophenyl)-3,3,6,6-tetramethyl-3,4,6,7,9,10-hexahydro-1,8(2H,5H)-acridinedione (847658-75-7)

Guidance literature:

With calcium chloride; zinc; In ethanol; water; for 2h; Heating;

DOI:10.1021/ol047463k

Reference yield:

4-aminobenzaldehyde (556-18-3,28107-09-7) + dimedone (126-81-8) → 9-(4-aminophenyl)-3,3,6,6-tetramethyl-3,4,6,7,9,10-hexahydro-1,8(2H,5H)-acridinedione (847658-75-7)

Guidance literature:

With ferrite; ammonium acetate; In neat (no solvent); at 120 ℃;

DOI:10.13005/ojc/310347

Reference yield:

4-nitrobenzaldehdye (555-16-8) → 9-(4-aminophenyl)-3,3,6,6-tetramethyl-3,4,6,7,9,10-hexahydro-1,8(2H,5H)-acridinedione (847658-75-7)

Guidance literature:

Multi-step reaction with 3 steps

1: methanol; H₂O / Heating

2: ammonium acetate; acetic acid / 6 h / Heating

3: 70 percent / zinc; CaCl₂ / ethanol; H₂O / 2 h / Heating

With ammonium acetate; acetic acid; calcium chloride; zinc; In methanol; ethanol; water;

DOI:10.1021/ol047463k

upstream raw materials:

3,3,6,6-tetramethyl-9-(4-nitrophenyl)-1,8-dioxodecahydroacridine

2-[(4,4-dimethyl-2,6-dioxocyclohexyl)-(4-nitrophenyl)methyl]-5,5-dimethylcyclohexane-1,3-dione

4-nitrobenzaldehdye

dimedone

Downstream raw materials:

9-(4-salicylideneaminophenyl)-3,3,6,6-tetramethyl-3,4,6,7,9,10-hexahydro-1,8(2H,5H)-acridinedione

9-(4-(bis(pyridine-2-ylmethyl)amino)phenyl)-3,3,6,6-tetramethyl-3,4,6,7,9,10-hexahydro-1,8(2H,5H)-acridinedione

N-[4-{3,3,6,6-tetramethyl-3,4,6,7,9,10-hexahydro-1,8(2H,5H)acridinedion-9-yl}phenyl]lipoic acid amide