325856-06-2

Basic information

• Product Name: 1,6-DiMethylquinolin-4(1H)-one
• Synonyms: 1,6-DiMethylquinolin-4(1H)-one;1,6-Dimethyl-1H-quinolin-4-one;1,6-dimethyl-4(1H)-quinolinone
• CAS NO: 325856-06-2
• Molecular Formula: C₁₁H₁₁NO
• Molecular Weight: 173.21114
• Mol File: 325856-06-2.mol

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 1,6-DiMethylquinolin-4(1H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 1,6-DiMethylquinolin-4(1H)-one(325856-06-2)
• EPA Substance Registry System: 1,6-DiMethylquinolin-4(1H)-one(325856-06-2)

Safety Data

• Hazardous Substances Data: 325856-06-2(Hazardous Substances Data)

Usage

Structure

Aromatic compound with a quinoline ring, two methyl substituents at the 1 and 6 positions, and a carbonyl group at the 4 position.

Type

Organic compound

Applications

a. Synthesis of pharmaceutical compounds
b. Building block in organic chemistry reactions

Biological activities

Potential biological activities; studied for pharmacological properties

Usage

Research and industrial applications

Upstream product

• 23432-40-8 6-methyl-4(1H)-quinolinone 
• 74-88-4 methyl iodide 
• 1399859-09-6 1-[5-methyl-2-(methylamino)phenyl]propan-1-one 
• 623-08-5 N-methyl-p-toluidine 
• 107-31-3 Methyl formate 
• 106-49-0 p-toluidine 

Relevant articles and documents

Synthesis of bridged benzazocines and benzoxocines by a titanium-catalyzed double-reductive umpolung strategy

A sequence of two titanium(III)-catalyzed reductive umpolung reactions is reported that allows the rapid construction of benzazo- and benzoxozine building blocks. The first step is a reductive cross-coupling of quinolones or chromones with Michael acceptors. This reaction proceeds with complete syn-selectivity for the quinolone functionalization while the anti-diastereomers are obtained as the major products from chromones. With different reaction conditions, the stereochemical outcome can be altered to afford the syn-chromanone products as well. A subsequent reductive ketyl radical cyclization forges the tricyclic title compounds in good yields. A stereochemical model explaining the observed stereoselectivities is provided and the product configurations were unambiguously verified by X-ray analyses and 2D NMR spectroscopic experiments.

Synthesis of 4-quinolones through nickel-catalyzed intramolecular amination on the β-carbon of o-(N-alkylamino)propiophenones

o-(N-Alkylamino)propiophenones are converted into 4-quinolones in the presence of chlorobenzene, potassium phosphate, morpholine, and nickel(0) catalyst. The reaction proceeds through the nickel-catalyzed formation of β-enaminones from o-(N-alkylamino)propiophenones and morpholine, followed by the intramolecular transamination. Georg Thieme Verlag Stuttgart · New York.

Direct C-3-alkenylation of quinolones via palladium-catalyzed C-H functionalization

An unprecedented C-3-alkenylation of quinolones was reported through palladium-catalyzed C-H functionalization with 1% catalyst loading. This method provides an efficient route to a variety of new quinolone derivatives.