Tropanols

The tropanols are derived from tropane , with a hydroxy substitution at the C-1, C-2 or C-3 atom. Two stereoisomers can be distinguished for the 2- and 3-tropanol . In the α-tropanols, the hydroxyl group is axial , in the β-tropanols equatorial to the ring system.

Tropanols
Surname	( 1R ) -1-tropanol	2α-tropanol	2β-tropanol	3α-tropanol	3β-tropanol
other names	1-hydroxytropane 8-methyl-8-azabicyclo [3.2.1] octan-1-ol	2α-hydroxytropane 8-methyl-8-azabicyclo [3.2.1] octan-2 endo -ol	2β-hydroxytropane 8-methyl-8-azabicyclo [3.2.1] octane-2 exo -ol	3α-hydroxytropane Tropine 8-methyl-8-azabicyclo [3.2.1] octan-3 endo -ol	3β-hydroxytropane Pseudotropin 8-methyl-8-azabicyclo [3.2.1] octane-3 exo -ol
Structural formula
CAS number		36127-54-5	36127-15-8	120-29-6	28390-68-3
PubChem		268139	54607705	8424
Molecular formula	C ₈ H ₁₅ NO
Molar mass	141.21 g mol ⁻¹
Melting point	47-48 ° C or 68-70 ° C	46-48 ° C	−10 ° C	63 ° C	108-109 ° C
boiling point			94-95 ° C	229 ° C	240-241 ° C

properties

The (1 R ) -1-tropanol is in a tautomeric equilibrium with ( R ) - (methylamino) cycloheptanone .

Occurrence

Deadly nightshade ( Atropa belladonna )

Tropanols and tropane alkaloids derived from them occur in several plant families , especially in the nightshade family ( Solanaceae ). For example in henbane ( Hyoscyamus niger ), in deadly nightshade ( Atropa belladonna ) and in various thorn apple species ( Datura spec.). The (1 R ) -1-tropanol can be found in the Andean berries ( Physalis peruviana ). Cochlearin with tropine as an alcohol component is also found in the common spoonbill ( Cochlearia officinalis , Brassicaceae ). The other families are: Proteaceae , Convolvulaceae , Euphorbiaceae , Rhizophoraceae, and Erythroxylaceae . It could be proven that the development of the enzymes necessary for biosynthesis in nightshade and redwood plants took place independently of one another.

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g Entry on 3α-tropanol. In: Römpp Online . Georg Thieme Verlag, accessed on January 29, 2013.
^ S. Sarel, E. Dykman: Hypoiodate-induced oxidative dimerization and functionalization of the tropane bicyclic system. In: Tetrahedron Lett. 17, 1976, pp. 3725-3728, doi: 10.1016 / S0040-4039 (00) 93093-4 .
^ ^A ^b D. E. Ayer, G. Büchi, PR Warnhoff, DM White: The structure of dioscorine. In: Journal of the American Chemical Society 80, 1958, pp. 6146-6146, doi: 10.1021 / ja01555a061 .
↑ ^a ^b W. AM Davies et al .: 703. An alkaloid of Dioscorea hispida, Dennstedt. Part VI. Some investigations on the synthesis of tropan-2-one. In: Journal of the Chemical Society . 1960, pp. 3504-3512, doi: 10.1039 / JR9600003504 .
↑ J. Jirschitzka, GW Schmidt et al .: Plant tropane alkaloid biosynthesis evolved independently in the Solanaceae and Erythroxylaceae. In: Proceedings of the National Academy of Sciences of the United States of America . Volume 109, Number 26, June 2012, pp. 10304-10309. doi: 10.1073 / pnas.1200473109 . PMID 22665766 . PMC 3387132 (free full text).

[Römpp-1] ↑ ^a ^b ^c ^d ^e ^f ^g Entry on 3α-tropanol. In: Römpp Online . Georg Thieme Verlag, accessed on January 29, 2013.

[Sarel-2] S. Sarel, E. Dykman: Hypoiodate-induced oxidative dimerization and functionalization of the tropane bicyclic system. In: Tetrahedron Lett. 17, 1976, pp. 3725-3728, doi: 10.1016 / S0040-4039 (00) 93093-4 .

[Ayer-3] A ^b D. E. Ayer, G. Büchi, PR Warnhoff, DM White: The structure of dioscorine. In: Journal of the American Chemical Society 80, 1958, pp. 6146-6146, doi: 10.1021 / ja01555a061 .

[Davies-4] W. AM Davies et al .: 703. An alkaloid of Dioscorea hispida, Dennstedt. Part VI. Some investigations on the synthesis of tropan-2-one. In: Journal of the Chemical Society . 1960, pp. 3504-3512, doi: 10.1039 / JR9600003504 .

[5] J. Jirschitzka, GW Schmidt et al .: Plant tropane alkaloid biosynthesis evolved independently in the Solanaceae and Erythroxylaceae. In: Proceedings of the National Academy of Sciences of the United States of America . Volume 109, Number 26, June 2012, pp. 10304-10309. doi: 10.1073 / pnas.1200473109 . PMID 22665766 . PMC 3387132 (free full text).