136423-40-0

Basic information

• Product Name: 3,4,5,6-tetrahydro-3-(2-phenylethyl)pyridin-2-one
• Synonyms: 3,4,5,6-tetrahydro-3-(2-phenylethyl)pyridin-2-one
• CAS NO: 136423-40-0
• Molecular Weight: 203.284
• Mol File: 136423-40-0.mol

Chemical Properties

• CAS DataBase Reference: 3,4,5,6-tetrahydro-3-(2-phenylethyl)pyridin-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4,5,6-tetrahydro-3-(2-phenylethyl)pyridin-2-one(136423-40-0)
• EPA Substance Registry System: 3,4,5,6-tetrahydro-3-(2-phenylethyl)pyridin-2-one(136423-40-0)

Safety Data

• Hazardous Substances Data: 136423-40-0(Hazardous Substances Data)

Upstream product

• 675-20-7 piperidin-2-one 
• 103-63-9 1-phenyl-2-bromoethane 
• 3553-93-3 1-(trimethylsilyl)piperidin-2-one 
• 17376-04-4 2-phenethyl iodide 

Downstream Products

• 269407-30-9 3-phenethylpiperidine-2-thione 

Relevant articles and documents

A one-pot bicycloannulation method for the synthesis of tetrahydroisoquinoline systems

A highly effective method for the synthesis of the core indolo[2,3- α]quinolizidine skeleton found in yohimbine is described. The reaction of N- monosubstituted thioamides with bromoalkenoyl chlorides furnishes thioisomunchnones as transient 1,3-dipoles that undergo ready intramolecular cycloaddition across the tethered π-bond to give thio-bicycloannulated products in a one-pot operation. The stereochemical outcome of the intramolecular reaction is the consequence of an endo cycloaddition of the neighboring π-bond across the transient thioisomunchnone dipole. A major limitation of the method is that when a hydrogen is present in the α- position of the thioamide the initially formed thio-N-acyliminium ion undergoes proton loss to produce a S,N-ketene acetal at a faster rate than dipole formation. Treatment of tetrahydro-β-carboline-1-thione with 2- bromooct-7-enoyl chloride followed by reductive removal of sulfur from the cycloadduct resulted in the formation of (±)-alloyohimbanone. Attempts to cycloadd the thioisomunchnone dipole across several nucleophilic π-bonds failed, and instead, products derived from cyclization of the π-bond onto the initially formed thio-N-acyliminium ion were formed. The resulting N,S- ketals were further converted into several tetrahydroisoquinoline alkaloids in good yield.

Piperidine derivatives

The invention provides piperidine derivatives of the general formula STR1 or an acid-addition salt or metal salt complex thereof, in which R represents a hydrogen atom or an optionally substituted alkyl, alkenyl, alkynyl, alkoxy, cycloalkyl, aryl, arylcarbonyl, heterocyclyl or heterocyclyloxy group; R1 represents an optionally substituted alkyl, phenyl, benzyl or cycloalkyl group; R2 represents a hydrogen atom or an optionally substituted alkyl group; one of W and X represents --CH2 --, --CH2 CH2 -- or --O--, the other of W and X being --CH2 -- or --CH2 CH2 or X represents a single chemical bond; m is 0 or 1 and n represents an integer from 0 to 3; processes for their preparation; compositions containing such compounds and their use as fungicides.

Cyclic Allylamine-Enamine Systems. Part 9. Further Isomerisations Using Tris(triphenylphosphine)rhodium (I) Chloride and Their Synthetic Utility.

The isomerisations of four 6-membered cyclic allylamines to their cyclic enamine tautomers using tris(triphenylphosphine)rhodium chloride are demonstrated and in this way the five tetracycles cis- and trans-1-methyl-1,2,3,4,4a,5,6,11c-octahydro-7H-pyridocarbazoles, 10 and 11, 2-methyl-1,2,3,4,5,6,7,8-octahydro-1,5-methanoazoninoindole, 12, 2-methyl-2,3,4,5,6,11-hexahydro-1,5-methano-1H-azocinoindole, 15, and 2,3,4,5,6,7-hexahydro-1,5-methano-2-methyl-1H-azocinoindol-6-one ethylene acetal, 21, were synthesised.