267011-73-4

Basic information

• Product Name: (R)-(+)-6-phenylpiperidine-2,4-dione
• Synonyms: (R)-(+)-6-phenylpiperidine-2,4-dione
• CAS NO: 267011-73-4
• Molecular Weight: 189.214
• Mol File: 267011-73-4.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: (R)-(+)-6-phenylpiperidine-2,4-dione(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(+)-6-phenylpiperidine-2,4-dione(267011-73-4)
• EPA Substance Registry System: (R)-(+)-6-phenylpiperidine-2,4-dione(267011-73-4)

Safety Data

• Hazardous Substances Data: 267011-73-4(Hazardous Substances Data)

Upstream product

• 267011-72-3 methyl (S_S,R)-(+)-methyl 3-oxo-5-phenyl-5-(p-toluenesulfinylamino)pentanoate 
• 5394-63-8 2,2,6-trimethyl-4H-1,3-dioxin-4-one 
• 253665-35-9 (1S,2R,4R,S_S)-7,7-dimethyl-N-(phenylmethylene)-2-(trimethylsilyloxy)bicyclo[2.2.1]heptane-1-methanesulfinamide 
• 130573-43-2 (2,2-dimethyl-6-methylene-6H-1,3-dioxin-4-yloxy)trimethylsilane 
• 614-19-7 (R)-3-phenyl-3-aminopropionic acid 
• 103-26-4 Methyl cinnamate 
• 158009-86-0 (S_S,3R)-(+)-methyl 3-[N-(p-toluenesulfinyl)amino]-3-(phenyl)propanoate 
• 350479-90-2 (S,E)-N-benzylidene-4-methylbenzenesulfinamide 
• 65451-19-6 N-(phenylacetyl)-3-amino-3-phenylpropanoic acid 
• 3646-50-2 3-Amino-3-phenylpropionic acid 
• 1050324-77-0 (R)-3-phenyl-3-(2,2,2-trifluoroacetamido)propanoic acid 

Downstream Products

• 267011-74-5 (R)-9-Phenyl-1,4-dithia-8-aza-spiro[4.5]decan-7-one 
• 326477-44-5 (4S,6R)-(+)-4-Hydroxy-6-phenylpiperidin-2-one 
• 326477-43-4 (4R,6R)-(+)-4-Hydroxy-6-phenylpiperidin-2-one 
• 212560-70-8 (+)-(6R)-6-phenylpiperidin-2-one 
• 3466-80-6 (R)-(+)-6-phenylpiperidine 
• 326477-50-3 (2R,4S)-(+)-4-Acetoxy-2-phenyl-1-trifluoroacetylpiperidine 
• 326477-47-8 (2R,4S)-(+)-2-Phenylpiperidine-4-ol 

Relevant articles and documents

Regioselective synthesis of substituted piperidine-2,4-diones and their derivatives via Dieckmann cyclisations

Abstract A flexible route to piperidine-2,4-diones variously substituted at the 6-, 5,6- and 2,6-positions, both with and without 1-substitution, is described; no N-protective group is required. A related regioselective Dieckmann cyclisation is also described that uses Davies' α-methylbenzylamine auxiliary and affords 6-substituted piperidine-2,4-diones enantioselectively.

Addition of dienolates to sulfinimines. Stereoselective synthesis of dihydropyridones

The vinylogous Mannich reaction of sulfinimines with dienolates was investigated. Lithium and trimethylsilyl enolates of ethyl 3-ethoxycrotonate reacted with enantiopure 10-isobornylsulfinimines to give derivatives of δ-aminoacids which were cyclised to 6-aryl substituted derivatives of 2(1H)-pyridinones. 6-Aryl substituted 2,4-piperidinediones with either (S) or (R) configuration were analogously obtained using lithium and TMS enolates of 2,2,6-trimethyl-1,3-dioxin-4-one.

An expedient synthesis of 6-arylpiperidine-2,4-diones by chain-extension of β-aryl-β-aminoacids

The synthesis of novel 6-arylpiperidine-2,4-diones is described in five steps starting from β-aryl-β-aminoacids via the chain extension of the latter into δ-aryl-δ-amino-β-ketoacids. The chemical pathway involves an acylation of Meldrum's acid and yields useful building blocks for heterocyclic chemistry.