62334-03-6

Basic information

• Product Name: N-benzylcrinasiadine
• Synonyms: N-benzylcrinasiadine
• CAS NO: 62334-03-6
• Molecular Weight: 329.355
• Mol File: 62334-03-6.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: N-benzylcrinasiadine(CAS DataBase Reference)
• NIST Chemistry Reference: N-benzylcrinasiadine(62334-03-6)
• EPA Substance Registry System: N-benzylcrinasiadine(62334-03-6)

Safety Data

• Hazardous Substances Data: 62334-03-6(Hazardous Substances Data)

Upstream product

• 30319-93-8 5-benzyl-(4ar,11bt)-1,3,4,4a,5,11b-hexahydro-2H-[1,3]dioxolo[4,5-j]phenanthridin-6-one 
• 51873-54-2 benzo[1,3]dioxole-5-carboxylic acid benzyl-cyclohex-1-enyl-amide 
• 100-44-7 benzyl chloride 
• 58169-37-2 (4ar,11bt)-3,4a,5,11b-tetrahydro-4H-[1,3]dioxolo[4,5-j]phenanthridin-6-one 
• 201230-82-2 carbon monoxide 
• 76464-99-8 N-benzyl-2-iodoaniline 
• 717903-52-1 6-(trimethylsilyl)benzo[d][1,3]dioxol-5-yl triflate 
• 224-11-3 trisphaeridine 
• 100-39-0 benzyl bromide 

Relevant articles and documents

Ligand controlled regiodivergent C1 insertion on arynes for construction of phenanthridinone and acridone alkaloids

A palladium-catalyzed regiodivergent C1 insertion multicomponent reaction involving aryne, CO, and 2-iodoaniline is established to construct the scaffolds of phenanthridinone and acridone alkaloids. Regioselective control is achieved under the guidance of selective ligands. The phenanthridinones are solely obtained under ligand-free condition. In comparison, application of the electron-abundant bidentate ligand dppm afforded the acridones with high efficiency. The release rate of the aryne from the precursor assists the regioselectivity of insertion as well, which was revealed through interval NMR tracking. A plausible mechanism was suggested based on the control experiments. Representative natural products and two types of natural product analogues were synthesized divergently through this tunable method. Divergent alkaloid synthesis: A multicomponent, regioselective approach for palladium-catalyzed C1 insertion is described. This reaction was applied in the divergent synthesis of phenanthridinone and acridone natural product core scaffolds.

Carbene-catalyzed aerobic oxidation of isoquinolinium salts: Efficient synthesis of isoquinolinones

A mild and environmentally friendly carbene-catalyzed aerobic oxidation of isoquinolinium salts was successfully realized. Accordingly, a diverse set of isoquinolinones and phenanthridinones was efficiently prepared in good to excellent yields. The mechanistic study indicates that the formation of an aza-Breslow intermediate is the crucial step in this transformation. This reaction features ambient air as the sole oxidant and oxygen source, a broad substrate scope, and excellent functional-group tolerance and proceeds under mild reaction conditions. Furthermore, a highly efficient synthesis of bioactive molecules and natural products including N-methylcrinasiadine, N-isopentylcrinasiadine, N-phenethylcrinasiadine, isoindolo[2,1-b]isoquinolin-5(7H)-one, PJ-34, rac-Gusanlung D, rosettacin, 8-oxopseudopalmatine and ilicifoline B was accomplished.