125732-47-0

Basic information

• Product Name: 4-[(4-Methoxy-phenyl)-(2-piperidin-1-yl-cyclohex-1-enyl)-methyl]-5-methyl-2-phenyl-2,4-dihydro-pyrazol-3-one
• CAS NO: 125732-47-0
• Molecular Weight: 457.616
• Mol File: 125732-47-0.mol

Chemical Properties

• CAS DataBase Reference: 4-[(4-Methoxy-phenyl)-(2-piperidin-1-yl-cyclohex-1-enyl)-methyl]-5-methyl-2-phenyl-2,4-dihydro-pyrazol-3-one(CAS DataBase Reference)
• NIST Chemistry Reference: 4-[(4-Methoxy-phenyl)-(2-piperidin-1-yl-cyclohex-1-enyl)-methyl]-5-methyl-2-phenyl-2,4-dihydro-pyrazol-3-one(125732-47-0)
• EPA Substance Registry System: 4-[(4-Methoxy-phenyl)-(2-piperidin-1-yl-cyclohex-1-enyl)-methyl]-5-methyl-2-phenyl-2,4-dihydro-pyrazol-3-one(125732-47-0)

Safety Data

• Hazardous Substances Data: 125732-47-0(Hazardous Substances Data)

Upstream product

• 897030-43-2 (E)-4-(4-methoxybenzylidene)-5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one 
• 2981-10-4 1-(cyclohex-1-en-1-yl)piperidine 
• 135763-57-4 4-(4-Methoxy-phenyl)-3-methyl-1-phenyl-8a-piperidin-1-yl-1,4,4a,5,6,7,8,8a-octahydro-chromeno[2,3-c]pyrazole 

Relevant articles and documents

Dihydropyrans from 1,4-cycloaddition of enamines to arylmethylenepyrazolones. Polar character of the thermal rearrangement of the resulting cycloadducts

The inverse electron demand hetero-Diels-Alder reaction of arylmethylenepyrazolones with enamines results in the selective formation of 3,4-dihydro-2H-pyran derivatives. These cycloadducts under thermodynamic conditions, are transformed via the zwitterion, which can be captured in the presence of tetracyanoethylene (TCE), as the more stable Michael-type adducts. The zwitterion could also be the intermediate for the cyclic adducts.

MICHAEL-TYPE ADDITION REACTIONS OF SOME ENAMINES TO ARYLIDENEPYRAZOLONES

The reaction of the arylidenepyrazolones (1b-d) with 1-morpholinocyclohexene (E2) in refluxing acetonitrile leads to the less substituted alkylated enamines 3b-d.On the other hand, the more substituted alkylated enamines 2a-d are formed when 1a-d react under the same conditions with 1-piperidinocyclohexene (E1).The nature of the enamine in crucial.Nucleophilic attack of the enamine on the α,β-unsaturated carbonyl system of 1 gives rise to a zwitterionic intermediate which through α-proton loss leads to different Michael-type adducts depending on the enamine.