548-31-2

Basic information

• Product Name: 2,3-dimethoxy-12-methyl[1,3]benzodioxolo[5,6-c]phenanthridin-13(12H)-one
• Synonyms: (1,3)Benzodioxolo(5,6-c)phenanthridin-13(12H)-one, 2,3-dimethoxy-12-methyl-; [1,3]Benzodioxolo[5,6-c]phenanthridin-13(12H)-one, 2,3-dimethoxy-12-methyl-; 2,3-Dimethoxy-12-methyl[1,3]benzodioxolo[5,6-c]phenanthridin-13(12H)-one
• CAS NO: 548-31-2
• Molecular Formula: C₂₁H₁₇NO₅
• Molecular Weight: 363.3634
• Mol File: 548-31-2.mol
• Article Data: 18

Chemical Properties

• Boiling Point: 614.2°C at 760 mmHg
• Flash Point: 325.3°C
• Density: 1.361g/cm³
• Vapor Pressure: 5.08E-15mmHg at 25°C
• Refractive Index: 1.668
• CAS DataBase Reference: 2,3-dimethoxy-12-methyl[1,3]benzodioxolo[5,6-c]phenanthridin-13(12H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-dimethoxy-12-methyl[1,3]benzodioxolo[5,6-c]phenanthridin-13(12H)-one(548-31-2)
• EPA Substance Registry System: 2,3-dimethoxy-12-methyl[1,3]benzodioxolo[5,6-c]phenanthridin-13(12H)-one(548-31-2)

Safety Data

• Hazardous Substances Data: 548-31-2(Hazardous Substances Data)

Usage

Molecular structure

Contains a benzodioxole ring system and a phenanthridinone core

Occurrence

Naturally occurring alkaloid found in several plant species

Medicinal properties

Potential antioxidant, anti-inflammatory, and anticancer effects

Cancer treatment potential

Ability to inhibit cancer cell growth and induce apoptosis

Other potential treatments

Microbial infections, cardiovascular diseases, and neurodegenerative disorders

Ongoing research

To explore the full range of its medicinal properties and potential pharmaceutical uses.

Upstream product

• 94656-60-7 nitidine φ-cyanide 
• 1207666-57-6 3-(benzo[d][1,3]dioxol-5-yl)-4-(2-hydroxyethyl)-6,7-dimethoxy-2-methylisoquinolin-1(2H)-one 
• 82463-72-7 2-bromo-4,5-dimethoxy-N-methylbenzenemethanamine 
• 1072952-49-8 4,5-dimethoxy-2-(methoxycarbonyl)benzeneboronic acid 
• 349107-92-2 N-(tert-butyl)-3,4-dimethoxybenzamide 
• 55171-31-8 2,3-methylenedioxy-8,9-dimethoxybenzophenanthridin-6(5H)-one 
• 74-88-4 methyl iodide 
• 3535-37-3 3,4-dimethoxybenzoic acid chloride 
• 66471-32-7 2-bromo-4,5-dimethoxy-N-methyl-N-(6′,7′-methylenedioxynaphthalen-1-yl)benzamide 
• 55171-64-7 2-bromo-4,5-dimethoxy-N-(6′,7′-methylenedioxynaphthalen-1-yl)benzamide 
• 1620902-98-8 6,7-methylenedioxy-1-(2,2,2-trichloromethylcarbonylamino)naphthalene 
• 1620902-92-2 6,7-methylenedioxy-1-(2,2,2-trichloromethylcarbonylamino)-1,4-dihydronaphthalene 
• 1620902-84-2 (2E)-3-(2-allyl-4,5-methylenedioxyphenyl)prop-2-en-1-ol 
• 1620902-77-3 ethyl (2E)-3-(2-allyl-4,5-methylenedioxyphenyl)prop-2-enoate 

Downstream Products

• 41349-35-3 Nitidine methyl sulfate 
• 119276-08-3 2,3-dimethoxy-12-methyl-[1,3]dioxolo[4',5':4,5]benzo[1,2-c]phenanthridinium; acetate 
• 13063-04-2 nitidine chloride 
• 114253-63-3 O-methyl-6-oxofagaronine 
• 13063-06-4 dihydronitidine 

Relevant articles and documents

A combined pathway for the synthesis of nitidine family alkaloids

Three related alkaloids, oxynitidine, nitidine and 5,6-dihydronitidine, have been afforded by the new synthetic protocols. In this approach, the Ni-catalyzed annulation reaction is indicated as the key step to construct the isoquinolinone core structure. The subsequent transformations lead to the target alkaloids.

Oxidative C?H/C?H Cross-Coupling Reactions between N-Acylanilines and Benzamides Enabled by a Cp*-Free RhCl3/TFA Catalytic System

By making use of a dual-chelation-assisted strategy, a completely regiocontrolled oxidative C?H/C?H cross-coupling reaction between an N-acylaniline and a benzamide has been accomplished for the first time. This process constitutes a step-economic and highly efficient pathway to 2-amino-2′-carboxybiaryl scaffolds from readily available substrates. A Cp*-free RhCl3/TFA catalytic system was developed to replace the [Cp*RhCl2]2/AgSbF6 system generally used in oxidative C?H/C?H cross-coupling reactions between two (hetero)arenes (Cp=pentamethylcyclopentadienyl, TFA=trifluoroacetic acid). The RhCl3/TFA system avoids the use of the expensive Cp* ligand and AgSbF6. As an illustrative example, the procedure developed herein greatly streamlines the total synthesis of the naturally occurring benzo[c]phenanthridine alkaloid oxynitidine, which was accomplished in excellent overall yield.

Palladium-catalyzed tandem reaction to construct benzo[c]phenanthridine: Application to the total synthesis of benzo[c]phenanthridine alkaloids

A concise and efficient synthesis of benzo[c]phenanthridines was accomplished by the palladium-catalyzed ring-opening coupling of azabicyclic alkene with o-iodobenzoates, followed by tandem cyclization. The strategy was successfully applied in the total synthesis of benzo[c]phenanthridine alkaloids such as sanguinarine, chelerythrine, nitidine and avicine.