Trögersche Base

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Structural formula
The two enantiomers of Tröger's base: (5S, 11S) - (-) - form (top) and (5R, 11R) - (+) - form (bottom).
(5 S , 11 S ) - (-) - shape (top) and (5 R , 11 R ) - (+) - shape (bottom)
General
Surname Trögersche Base
other names
  • (±) -2,8-dimethyl-6 H , 12 H -5,11-methanodibenzo [ b , f ] [1,5] diazocin
  • (1 RS , 9 RS ) -5,13-dimethyl-1,9-diazatetracyclo [7.7.1.0 2.7 .0 10.15 ] heptadeca-2 (7), 3.5.10 (15), 11, 13-hexaen
Molecular formula C 17 H 18 N 2
External identifiers / databases
CAS number
  • 529-81-7 (racemate)
  • 21451-74-1 [(5 R , 11 R ) - (+) - form]
EC number 621-668-5
ECHA InfoCard 100.150.499
PubChem 196981
ChemSpider 170601
Wikidata Q410493
properties
Molar mass 250.34 g mol −1
Physical state

firmly

Melting point

133-136 ° C

safety instructions
GHS labeling of hazardous substances
07 - Warning

Caution

H and P phrases H: 315-319-335
P: 261-305 + 351 + 338
Toxicological data

56.2 mg kg −1 ( LD 50 ,  mouse ,  iv )

As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

The Tröger's base is after its discoverer, the chemist Julius Tröger (1862-1942), named heterocyclic compound corresponding to the organic is attributed chemistry.

structure

Tröger's base contains two pyramidal nitrogen atoms that form stereocenters. As a rule, the inversion of pyramidal nitrogen atoms with three different radicals (and a lone pair of electrons) proceeds very quickly, so that such substances racemize quickly - not so with Tröger's base. In Tröger's base, both nitrogen atoms are in a bridgehead position, making a pyramidal inversion impossible. There are therefore two stable enantiomers of Tröger's base that can be separated, for example, by chromatography on a chiral stationary phase.

Manufacturing

Tröger's base was first synthesized in 1887 from p -toluidine and formaldehyde in acidic solution. The correct structural formula was not determined until 1935. Tröger's base can also be prepared from p -toluidine, dimethyl sulfoxide (DMSO) and hydrochloric acid or p -toluidine and urotropine (hexamethylenetetramine). All these synthetic methods lead to the racemate of Tröger's base.

Individual evidence

  1. ↑ a b c d e data sheet Trögersche Base at Sigma-Aldrich , accessed on July 11, 2011 ( PDF ).Template: Sigma-Aldrich / name not given
  2. ^ Siegfried Hauptmann : Organic Chemistry , 2nd Edition, VEB Deutscher Verlag für Grundstoffindindustrie, Leipzig, 1985, p. 96, ISBN 3-342-00280-8 .
  3. ^ Ernest L. Eliel, Samuel H. Wilen: Stereochemistry of Organic Compounds , John Wiles & Sons, 1994, p. 360, ISBN 0-471-05446-1 .
  4. ↑ Julius Tröger: About some bases formed by means of nascent formaldehyde. In: Journal for Practical Chemistry . 36, 1887, pp. 225-245, doi : 10.1002 / prac.18870360123 .
  5. ^ MA Spielman: The Structure of Troeger's Base. In: Journal of the American Chemical Society 57, 1935, pp. 583-585, doi : 10.1021 / ja01306a060 .
  6. ↑ Zhong Li, Xiaoyong Xu, Yanqing Peng, Zhaoxing Jiang, Chuanyong Ding, Xuhong Qian: An Unusual Synthesis of Troeger's Bases Using DMSO / HCl as Formaldehyde Equivalent. In: Synthesis 2005, pp. 1228-1230, doi : 10.1055 / s-2005-861868 .
  7. ↑ Thierry Masa, Carmen Pardo, José Elguero: A shorter synthesis of symmetrical 2,11-dimethyl-bis-Tröger's bases. A new molecular tweezer. In: Arkivoc . 2004, (EM-973K).