Tropane

Structural formula
General
Surname	Tropane
other names	8-methyl-8-azabicyclo [3.2.1] octane
Molecular formula	C 8 H 15 N
External identifiers / databases
EC number	628-350-5
ECHA InfoCard	100.156.627
PubChem	637986
Wikidata	Q410271
properties
Molar mass	125.21 g mol −1
density	0.9307 g cm −3
boiling point	162-164 ° C
safety instructions
GHS hazard labeling ; no classification available
GHS hazard labeling ; no classification available
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Tropane is a bicyclic organic compound. The basic structure of the compound is contained in substance classes such as tropanols or tropane alkaloids , which are important as drugs and toxins . The name is derived from atropine , in whose molecule it is contained as a structural element.

Presentation and extraction

A synthesis described by Robinson and Schöpf as early as 1935 starts with a Mannich reaction of succindialdehyde and methylamine with dimethyl acetone dicarboxylate . The tropane basic structure is already formed. The carboxylic ester substitution is removed by acidic ester cleavage and subsequent thermal decarboxylation. The target compound is obtained from the tropinone obtained by reduction using hydrazine or hydrogenation over platinum (IV) oxide .

Basic structure

Tropane backbone ( nortropane , center) compared to pyrrolidine (left) and piperidine (right).

The basic structure of tropane is a heterocyclic ring system in which the C-1 and C-5 atoms of a piperidine ring are connected to one another by an ethylene group. The ring system can also be interpreted as a pyrrolidine ring , in which the carbon atoms 1 and 4 are connected to one another by a propylene group. Tropane also has a methyl group on the nitrogen (position 8) . If the methyl group is missing, it is called nortropane .

Individual evidence

↑ v. Auwers: In J. Practical Chemistry . 105, 1922, p. 110.
↑ J.-L. Imbach, AR Katritzky, RA Kolinski: The conformational analysis of heterocyclic systems. Part VIII. Kinetics of quaternization of N-alkylpiperidines and N-alkylpiperazines in acetonitrile. In: J. Practical Chemistry . B, 1966, pp. 556-562, doi: 10.1039 / J29660000556 .
↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
↑ Entry on tropane alkaloids. In: Römpp Online . Georg Thieme Verlag, accessed on June 13, 2014.
^ S. Hauptmann, J. Graefe, H. Remane: Textbook of organic chemistry. German publishing house for basic industry, Leipzig 1980, p. 624.
↑ P. Wagner, Y. Nakagawa, GS Lee, ME Davis, S. Elomari, RC Medrud, SI Zones: Guest / Host Relationships in the Synthesis of the Novel Cage-Based Zeolites SSZ-35, SSZ-36, and SSZ- 39. In: J. Am. Chem. Soc. 122, 2000, pp. 263-273 doi: 10.1021 / ja990722u .
^ W. Wysocka: Hydrogenolytic Cleavage of C = O Bond in γ-Piperidone Derivatives. In: Heterocycles . 19, 1982, pp. 1-5, doi: 10.3987 / R-1982-01-0001 .

[1] v. Auwers: In J. Practical Chemistry . 105, 1922, p. 110.

[2] J.-L. Imbach, AR Katritzky, RA Kolinski: The conformational analysis of heterocyclic systems. Part VIII. Kinetics of quaternization of N-alkylpiperidines and N-alkylpiperazines in acetonitrile. In: J. Practical Chemistry . B, 1966, pp. 556-562, doi: 10.1039 / J29660000556 .

[NV-3] This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.

[Römpp-4] Entry on tropane alkaloids. In: Römpp Online . Georg Thieme Verlag, accessed on June 13, 2014.

[5] S. Hauptmann, J. Graefe, H. Remane: Textbook of organic chemistry. German publishing house for basic industry, Leipzig 1980, p. 624.

[6] P. Wagner, Y. Nakagawa, GS Lee, ME Davis, S. Elomari, RC Medrud, SI Zones: Guest / Host Relationships in the Synthesis of the Novel Cage-Based Zeolites SSZ-35, SSZ-36, and SSZ- 39. In: J. Am. Chem. Soc. 122, 2000, pp. 263-273 doi: 10.1021 / ja990722u .

[7] W. Wysocka: Hydrogenolytic Cleavage of C = O Bond in γ-Piperidone Derivatives. In: Heterocycles . 19, 1982, pp. 1-5, doi: 10.3987 / R-1982-01-0001 .