83019-09-4

Basic information

• Product Name: cis-2-methyl-6-tridecylpiperidine
• CAS NO: 83019-09-4
• Molecular Weight: 281.525
• Mol File: 83019-09-4.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: cis-2-methyl-6-tridecylpiperidine(CAS DataBase Reference)
• NIST Chemistry Reference: cis-2-methyl-6-tridecylpiperidine(83019-09-4)
• EPA Substance Registry System: cis-2-methyl-6-tridecylpiperidine(83019-09-4)

Safety Data

• Hazardous Substances Data: 83019-09-4(Hazardous Substances Data)

Upstream product

• 10157-76-3 dodecyl 4-methylbenzenesulphonate 
• 112-53-8 1-dodecyl alcohol 
• 83019-12-9 6-Methyl-2-tridecyl-2,3,4,5-tetrahydro-pyridine 
• 93297-98-4 nonadecane-2,6-dione 

Relevant articles and documents

Rapid configuration analysis of the solenopsins

A protocol for rapid access to the relative and absolute configurations of the solenopsins, the venom alkaloids of fire ants (Solenopsis spp.), was developed based on chiral capillary gas chromatography. The synthesis of racemic mixtures of 2-methyl-6-alkylpiperidines and the isolation of natural (2R,6R)- and (2R,6S)-2-methyl-6-undecylpiperidines allowed for the standardization of the chromatographic method. Application of this protocol revealed the previously unknown natural occurrence of four stereoisomers of 2-methyl-6-undecylpiperidine in venom samples from workers and gynes of Solenopsis saevissima.

Organoaluminum-Promoted Beckmann Rearrangement of Oxime Sulfonates

The Beckmann rearrangement of oxime sulfonates with simultaneous nucleophilic trapping of the intermediary iminocarbocation by organoaluminum reagents is described.This process provides a new and highly efficient route to imino thioethers, imino selenoethers, imino nitriles, and α-alkylated amines starting from oxime sulfonates by the use of dialkylaluminum thiolates, selenolates, diethylaluminum chloride-trimethylsilyl cyanide, and trialkylaluminum-diisobutylaluminum hydride systems, respectively.The present organoaluminum-promoted Beckmann rearrangement of oxime sulfonates has been successfully applied to the synthesis of naturally occuring alkaloids, pumiliotoxin C and solenopsin A and B, in stereoselective fashion.Moreover, α,α-dialkylation of amines can be realized by the successive treatment of oxime sulfonates with trialkylaluminum followed by allylic or propargylic Grignard reagents in synthetically useful yields.