6391-66-8

Basic information

• Product Name: 2,3,4,6-Tetrahydro-2,2-dimethyl-5H-pyrano[3,2-c]quinolin-5-one
• Synonyms: 2,3,4,6-Tetrahydro-2,2-dimethyl-5H-pyrano[3,2-c]quinolin-5-one
• CAS NO: 6391-66-8
• Molecular Formula: C₁₄H₁₅NO₂
• Molecular Weight: 229.27
• Mol File: 6391-66-8.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2,3,4,6-Tetrahydro-2,2-dimethyl-5H-pyrano[3,2-c]quinolin-5-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,4,6-Tetrahydro-2,2-dimethyl-5H-pyrano[3,2-c]quinolin-5-one(6391-66-8)
• EPA Substance Registry System: 2,3,4,6-Tetrahydro-2,2-dimethyl-5H-pyrano[3,2-c]quinolin-5-one(6391-66-8)

Safety Data

• Hazardous Substances Data: 6391-66-8(Hazardous Substances Data)

Usage

General Description

2,3,4,6-Tetrahydro-2,2-dimethyl-5H-pyrano[3,2-c]quinolin-5-one is a chemical compound with a complex structure that contains a fused pyranoquinoline ring system. It is a heterocyclic compound that is used in the pharmaceutical industry for the synthesis of various bioactive molecules. 2,3,4,6-Tetrahydro-2,2-dimethyl-5H-pyrano[3,2-c]quinolin-5-one has potential pharmacological properties and is being studied for its potential use as an antiviral, antifungal, and anticancer agent. It is also used as a building block for the synthesis of other heterocyclic compounds and has potential applications in medicinal chemistry and drug discovery. However, further research is needed to fully understand its properties and potential uses.

Upstream product

• 50-00-0 formaldehyd 
• 70254-43-2 4-Hydroxy-2-quinolone 
• 541-47-9 3-Methylbutenoic acid 
• 78-79-5 isoprene 
• 70254-44-3 2,4-dihydroxyquinoline 
• 107-86-8 3,3-dimethyl acrylaldehyde 
• 523-64-8 flindersine 
• 62-53-3 aniline 
• 91794-23-9 4-keto-2,2-dimethyl-3,4,5,6-tetrahydro-2H-pyrano<3,2-c>quinolin-5-one 
• 14872-56-1 5-isopropyl-2-oxo-tetrahydro-furan-3-carboxylic acid ethyl ester 
• 870-63-3 prenyl bromide 
• 111094-76-9 2-methyl-2-chloromercurymethyl-3,4-dihydro-2H,5H-pyrano{3,2-c}quinolin-5-one 
• 109573-19-5 4-hydroxy-3-(3-methylbut-3-enyl)quinolin-2(1H)-one 
• 109573-27-5 4-hydroxy-3-(3-hydroxy-3-methylbutyl)quinolin-2(1H)-one 

Downstream Products

• 523-64-8 flindersine 

Relevant articles and documents

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A Chiral Phenanthroline Ligand with a Hydrogen-Bonding Site: Application to the Enantioselective Amination of Methylene Groups

A silver-catalyzed amination is reported that occurs at the aliphatic C3-substituent of various quinolones and pyridones. The C-H amination reaction proceeded with high site-and enantioselectivity (14 examples, 83-97% ee). The key to its success is the use of a chiral phenanthroline ligand that is attached via an ethynyl linker to the 8-position of octahydro-1H-4,7-methanoisoindol-1-one. AgPF6 (10 mol %) served as the silver source, PhI.NNs as the nitrene precursor, and 1,10-phenanthroline as the coligand. The reaction outcome can be understood by assuming a nitrene C-H insertion within a hydrogen-bonded silver complex in which a single C-H bond is exposed to the catalytic reaction center.

Simple efficient synthesis of pyranoquinoline alkaloids: Flindersine, khaplofoline, haplamine and their analogues

An efficient two step synthesis of pyranoquinoline alkaloids is described. Direct treatment of isoprene with 4-hydroxyquinolin-2(1H)-one in the presence of polyphosphoric acid furnished dihydroflindersine in good yield, and which on dehydrogenation led to a new synthesis of flindersine. Khaplofoline, a linear pyranoquinoline alkaloid, was obtained as a minor product. The syntheses of derivatives are also documented.

A NEW APPROACH TO HEMITERPENOID TRICYCLIC QUINOLONES. SYNTHESIS OF N-METHYLFLINDERSINE, KHAPLOPHOLINE AND OTHER STRUCTURALLY SIMILAR ALKALOIDS

A new and general synthesis of tricyclic quinolone alkaloids is described which, by cyclization of 3-butenyl-4-hydroxyquinolones promoted by mercury(II) ion or by formic acid, affords pyranoquinolones and pyranoquinolones, respectively, with regio- and site-selectivity better than those obtained employing known methodologies. 3-Butenyl-4-hydroxyquinolones have been reacted with mercury(II) acetate to give, after work-up, the corresponding 2-(chloromercurymethyl)pyranoquinolones, which have been reductively demercurated with sodium borohydride and then dehydrogenated by treatment with DDQ.Alternatively, from the same starting compounds the "linear" isomers are obtained by formic acid-promoted cyclization.N-Methylflindersine, khaplofoline and other structurally similar alkaloids have been obtained.