32402-69-0

Basic information

• Product Name: 2(1H)-Pyridinone, 5-acetyl-3,4-dihydro-6-methyl-1-(phenylmethyl)-
• CAS NO: 32402-69-0
• Molecular Formula: C15H17NO2
• Molecular Weight: 243.305
• Mol File: 32402-69-0.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 2(1H)-Pyridinone, 5-acetyl-3,4-dihydro-6-methyl-1-(phenylmethyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2(1H)-Pyridinone, 5-acetyl-3,4-dihydro-6-methyl-1-(phenylmethyl)-(32402-69-0)
• EPA Substance Registry System: 2(1H)-Pyridinone, 5-acetyl-3,4-dihydro-6-methyl-1-(phenylmethyl)-(32402-69-0)

Safety Data

• Hazardous Substances Data: 32402-69-0(Hazardous Substances Data)

Upstream product

• 100-46-9 benzylamine 
• 123-54-6 acetylacetone 
• 814-68-6 acryloyl chloride 
• 21396-42-9 4-benzylaminopent-3-en-2-one 
• 23652-86-0 (Z)-4-(benzylamino)-3-penten-2-one 

Downstream Products

• 202188-62-3 1-benzyl-5-(1-hydroxyethyl)-6-methyl-1,2,3,4-tetrahydro-2-pyridinone 

Relevant articles and documents

Stereoselective synthesis of 5-alkyliden-6-aminotetrahydro-2-pyranones through an unexpected isomerization of the hydroxytetrahydro-2-pyridinones obtained by the selective reduction of acylated enaminones

A convenient methodology for the stem selective preparation of 5- alkyliden-6-aminotetrahydro-2-pyranone 4 is reported. The synthesis of 2- pyranone 4 occurs through an unknown isomerization mechanism of the hydroxytetrahydro-2-pyridinone 3 an accessible starting material obtained by mild and selective reduction of the 5-acyltetrahydro-2-pyridinone 2. The isomerization mechanism and the stereoselectivity in the synthesis of 2- pyranone 4 was investigated and rationalized.

Heterocycle Formation through Aza-Annulation: Stereochemically Controlled Syntheses of (+/-)-5-Epitashiromine and (+/-)-Tashiromine

N-alkenylamines, stabilized through conjugation with an electron-withdrawing group, undergo aza-annulation with acryloyl chloride to provide a convergent route for the construction of six-membered nitrogen heterocycles.In addition to enhancing the C-alkylation process of annulation relative to the competing N-acylation process, the electron withdrawing substituent controlled the regioselectivity of alkene formation in both the intermediate enamine and in the unsaturated lactam product.A variety of functional groups, which include -COMe, -COPh, -CO2R, -CONHPh, -CN, -P(O)(OEt)2, and -SO2Ph, were used to determine the effect of the electron-withdrawing substituents upon both the annulation reaction with acryloyl chloride and the subsequent hydrogenation process.When the enamide annulation product was stabilized through conjugation with ester or amide substituents, catalytic hydrogenation of the aza-annulation product resulted in the formation of vicinal stereocenters with high cis selectivity.The utility of this methodology was demonstrated by application of the condensation/aza-annulation/hydrogenation sequence as the key for construction and stereochemical control of the indolizidine ring system of (+/-)-tashiromine.