Jump to content

2,6-Dimethylpiperidine: Difference between revisions

From Wikipedia, the free encyclopedia
Content deleted Content added
Chem-awb (talk | contribs)
{{Chembox new --> {{Chembox, Replaced: {{Chembox new → {{chembox using AWB
No edit summary
Line 39: Line 39:
}}
}}


'''2,6-Dimethylpiperidines''' are [[chemical compound]]s with the formula C<sub>5</sub>H<sub>8</sub>(CH<sub>3</sub>)<sub>2</sub>NH. Two [[diastereomers]] exist: the achiral R,S isomer and the [[Chirality (chemistry)|chiral]] R,R/S,S pair. Dimethylpiperidines are derivatives of the [[heterocycle]] [[piperidine]], wherein two hydrogen atoms are replaced by [[methyl]] groups.
'''2,6-Dimethylpiperidines''' are [[chemical compound]]s with the formula C<sub>5</sub>H<sub>8</sub>(CH<sub>3</sub>)<sub>2</sub>NH. Two [[diastereomers]] exist: the achiral R,S isomer and the [[Chirality (chemistry)|chiral]] R,R/S,S [[enantiomer|enantiomeric]] pair. Dimethylpiperidines are derivatives of the [[heterocycle]] [[piperidine]], wherein two hydrogen atoms are replaced by [[methyl]] groups.


The 2,6-dimethylpiperidines are prepared by reduction of [[2,6-dimethylpyridine]] (2,6-lutidine). The R,S isomer is favored.
The 2,6-dimethylpiperidines are prepared by reduction of [[2,6-dimethylpyridine]] (2,6-lutidine). The R,S isomer is favored.

Revision as of 07:00, 12 November 2009

2,6-Dimethylpiperidine
Names
IUPAC name
2,6-Dimethylpiperidine
Other names
2,6-Lupetidine
Identifiers
3D model (JSmol)
ECHA InfoCard 100.007.256 Edit this at Wikidata
RTECS number
  • OK5775000
  • CC1CCCC(C)N1
Properties
C7H15N
Molar mass 113.20 g/mol
Appearance Colorless liquid
Density 0.84 g/mL
Boiling point 113.2
Low
Solubility in other solvents Most organic solvents
Basicity (pKb) ca. 10
1.4394
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Flammable
Flash point 53 °F
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

2,6-Dimethylpiperidines are chemical compounds with the formula C5H8(CH3)2NH. Two diastereomers exist: the achiral R,S isomer and the chiral R,R/S,S enantiomeric pair. Dimethylpiperidines are derivatives of the heterocycle piperidine, wherein two hydrogen atoms are replaced by methyl groups.

The 2,6-dimethylpiperidines are prepared by reduction of 2,6-dimethylpyridine (2,6-lutidine). The R,S isomer is favored.

The 2,6-dimethylpiperidines are of interest for their conformational properties. The R,S isomer exists largely in the chair conformation with equatorial methyl groups. The R,R/S,S isomers are attractive chiral secondary amine building blocks.[1]

References

  1. ^ Einhorn, J.; Einhorn, C.; Ratajczak, F.; Durif, A.; Averbuch, M.-T. and Pierre, J.-L., "Synthesis and resolution of a chiral analog of 2,2,6,6-tetramethylpiperidine and of its corresponding nitroxide", Tetrahedron Letters, 1998, volume 39, pages 2565-2568