6052-75-1

Basic information

• Product Name: 4-hydroxy-1,6-dimethyl-2(1H)-pyridinone
• Synonyms: 4-hydroxy-1,6-dimethyl-2(1H)-pyridinone;1-Methyl-4-hydroxy-6-methylpyridine-2(1H)-one;4-Hydroxy-1,6-dimethylpyridine-2(1H)-one;2-hydroxy-1,6-dimethyl-pyridin-4-one;4-Hydroxy-1,6-dimethyl-1H-pyridin-2-one
• CAS NO: 6052-75-1
• Molecular Formula: C₇H₉NO₂
• Molecular Weight: 139.16
• Mol File: 6052-75-1.mol
• Article Data: 5

Chemical Properties

• Melting Point: 225-226 °C (decomp)
• Boiling Point: 233.5°Cat760mmHg
• Flash Point: 95°C
• Appearance: /
• Density: 1.225g/cm³
• Vapor Pressure: 0.0103mmHg at 25°C
• Refractive Index: 1.564
• PKA: 4.50±1.00(Predicted)
• CAS DataBase Reference: 4-hydroxy-1,6-dimethyl-2(1H)-pyridinone(CAS DataBase Reference)
• NIST Chemistry Reference: 4-hydroxy-1,6-dimethyl-2(1H)-pyridinone(6052-75-1)
• EPA Substance Registry System: 4-hydroxy-1,6-dimethyl-2(1H)-pyridinone(6052-75-1)

Safety Data

• Hazardous Substances Data: 6052-75-1(Hazardous Substances Data)

Usage

InChI:InChI=1/C7H9NO2/c1-5-3-6(9)4-7(10)8(5)2/h3-4,10H,1-2H3

Upstream product

• 143456-22-8 2,2-dimethyl-5-(3-oxobutanoyl)-1,3-dioxane-4,6-dione 
• 675-10-5 4-hydroxy-6-methyl-2-pyron 
• 847983-04-4 2,2-dimethyl-5-[(Z)-3-methylamino-2-butenoyl]-1,3-dioxane-4,6-dione 
• 84259-90-5 (Z)-N-methyl-5-(methylamino)-3-oxohex-4-enamide 
• 74-89-5 methylamine 

Downstream Products

• 176683-50-4 4-Chloro-3-formyl-1,6-dimethyl-2(1H)-pyridone 
• 54885-36-8 4-hydroxy-1,6-dimethyl-3-(phenylthio)pyridin-2(1H)-one 
• 215609-20-4 4-Hydroxy-3-(4-methoxy-benzoyl)-1,6-dimethyl-1H-pyridin-2-one 
• 215609-05-5 2-Chloro-benzoic acid 1,6-dimethyl-2-oxo-1,2-dihydro-pyridin-4-yl ester 
• 95306-63-1 4-Benzylamino-1,6-dimethyl-1H-pyridin-2-one 
• 380634-00-4 C₁₁H₁₁NO₄ 
• 112423-11-7 4-Methoxy-1,6-dimethyl-3-phenyl-2(1H)-pyridinon 
• 1217597-35-7 2-amino-4-[1-(2-deoxy-β-D-ribosyl)-1,2,3,4-tetrahydropyrimidin-5-yl]-5,6-dihydro-6,7-dimethyl-5-oxo-4H-pyrano[3,2-c]pyridine-3-carbonitrile 
• 1217597-41-5 bis(1,2-dihydro-4-hydroxy-1,6-dimethyl-2-oxopyridin-3-yl)[1-(2-deoxy-β-D-ribosyl)-1,2,3,4-tetrahydropyrimidin-5-yl]methane 

Relevant articles and documents

Antiproliferative and apoptosis inducing properties of pyrano[3,2-c]pyridones accessible by a one-step multicomponent synthesis

4-Arylpyrano-[3,2-c]-pyridones have been prepared by a one-step cyclocondensation of 4-hydroxy-1,6-dimethylpyridin-2(1H)-one with various substituted benzaldehydes and malononitrile. These heterocycles exhibit micromolar and submicromolar antiproliferativ

Design, Synthesis, and Phenotypic Profiling of Pyrano-Furo-Pyridone Pseudo Natural Products

Natural products (NPs) inspire the design and synthesis of novel biologically relevant chemical matter, for instance through biology-oriented synthesis (BIOS). However, BIOS is limited by the partial coverage of NP-like chemical space by the guiding NPs. The design and synthesis of “pseudo NPs” overcomes these limitations by combining NP-inspired strategies with fragment-based compound design through de novo combination of NP-derived fragments to unprecedented compound classes not accessible through biosynthesis. We describe the development and biological evaluation of pyrano-furo-pyridone (PFP) pseudo NPs, which combine pyridone- and dihydropyran NP fragments in three isomeric arrangements. Cheminformatic analysis indicates that the PFPs reside in an area of NP-like chemical space not covered by existing NPs but rather by drugs and related compounds. Phenotypic profiling in a target-agnostic “cell painting” assay revealed that PFPs induce formation of reactive oxygen species and are structurally novel inhibitors of mitochondrial complex I.

Reactivite de la methyl-6 hydroxy-4 pyrone-2 vis-a-vis des amines primaires : synthese de pyridones-2 N-substituees et d'hexanamides intermediaires

In the well-documented (1-7) reaction of ammonia or primary amines with 2-pyrones leading to pyridones, the aliphatic intermediates have never been isolated, except for the reaction of 1 with aniline (8).In this work, the reaction of 4-hydroxy-6-methyl-2-pyrone 1 with various primary amines is studied.Three 5-amino-3-oxo-4-hexaneamides 3 are isolated for the first time and characterized by NMR, IR and mass spectra.The corresponding 4-hydroxy-6-methyl-2-pyridones 4 are obtained by heating intermediates 3.Direct attack of 1 by primary amines yields the same compounds 4 and finally leads to 4-alkyl (or phenyl) amino-6-methyl-2-pyridones 5.Thus, compounds of the type 5 are obtained from 4-hydroxy-6-methyl-2-pyrone 1 in for steps including three successive nucleophilic sustitutions by primary amines.