62322-75-2

Basic information

• Product Name: 2-Propen-1-one, 1-(4-methylphenyl)-3-(2-nitrophenyl)-
• CAS NO: 62322-75-2
• Molecular Formula: C16H13NO3
• Molecular Weight: 267.284
• Mol File: 62322-75-2.mol
• Article Data: 29

Chemical Properties

• CAS DataBase Reference: 2-Propen-1-one, 1-(4-methylphenyl)-3-(2-nitrophenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Propen-1-one, 1-(4-methylphenyl)-3-(2-nitrophenyl)-(62322-75-2)
• EPA Substance Registry System: 2-Propen-1-one, 1-(4-methylphenyl)-3-(2-nitrophenyl)-(62322-75-2)

Safety Data

• Hazardous Substances Data: 62322-75-2(Hazardous Substances Data)

Upstream product

• 1777-53-3 1-(p-tolyl)-2-(triphenylphosphoranylidene)ethanone 
• 552-89-6 2-nitro-benzaldehyde 
• 619-41-0 4-(bromoacetyl)toluene 
• 122-00-9 para-methylacetophenone 
• 552-16-9 ortho-nitrobenzoic acid 
• 5337-93-9 4'-methylpropiophenone 

Downstream Products

• 24667-94-5 2-(4-methylphenyl)quinoline 
• 887750-88-1 5-(2-nitro-phenyl)-1-phenyl-3-p-tolyl-4,5-dihydro-1H-pyrazole 
• 1198359-49-7 (R)-2-(4-methylphenyl)-1,2,3,4-tetrahydroquinoline 

Relevant articles and documents

Visible-light-driven Cadogan reaction

Visible-light-driven photochemical Cadogan-type cyclization has been discovered. The organic D-A type photosensitizer 4CzIPN found to be an efficient mediator to transfer energy from photons to the transient intermediate that breaks the barriers of deoxygenation in Cadogan reaction and enables a mild metal-free access to carbazoles and related heterocycles. DFT calculation results indicate mildly endergonic formation of the intermediate complex of nitrobiarenes and PPh3, which corresponds with experimental findings regarding reaction temperature. The robust synthetic capacity of the photoredox Cadogan reaction systems has been demonstrated by the viable productivity of a broad range of carbazoles and related N-heterocycles with good tolerance of various functionalities.

Synthesis of 1,4-dihydropyrazolo[4,3-b]indoles via intramolecular C(sp2)-N bond formation involving nitrene insertion, DFT study and their anticancer assessment

We herein report a new synthetic route for a series of unreported 1,4-dihydropyrazolo[4,3-b]indoles (6–8) via deoxygenation of o-nitrophenyl-substituted N-aryl pyrazoles and subsequent intramolecular (sp2)-N bond formation under microwave irradiation expedite modified Cadogan condition. This method allows access to NH-free as well as N-substituted fused indoles. DFT study and controlled experiments highlighted the role of nitrene insertion as one of the plausible reaction mechanisms. Furthermore, the target compounds exhibited cytotoxicity at low micromolar concentration against lung (A549), colon (HCT-116), and breast (MDA-MB-231, and MCF-7) cancer cell lines, induced the ROS generation and altered the mitochondrial membrane potential of highly aggressive MDA-MB-231 cells. Further investigations revealed that these compounds were selective Topo I (6h) or Topo II (7a, 7b) inhibitors.

Enantioselective Synthesis of Tetrahydroquinolines via One-Pot Cascade Biomimetic Reduction?

A novel and efficient protocol for the synthesis of chiral tetrahydroquinoline derivatives with excellent enantioselectivities and high yields has been developed through one-pot cascade biomimetic reduction. The detailed reaction pathway includes the acid-catalyzed and ruthenium-catalyzed formation of aromatic quinoline intermediates and biomimetic asymmetric reduction.