tropinone
Also known as 3-tropinone, 8-methyl-8-azabicyclo[3.2.1]octan-3-one, Tropinon, N-methyl-8-azabicyclo[3.2.1]octan-3-one, 1alphaH,5alphaH-tropan-3-one, (1R,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-one, Tropinona
Tropinone is an alkaloid, famously synthesised in 1917 by Robert Robinson as a synthetic precursor to atropine, a scarce commodity during World War I. Tropinone and the alkaloids cocaine and atropine all share the same tropane core structure. Its corresponding conjugate acid at pH 7.3 major species is known as tropiniumone.
Chemical data
- Formula
- C8H13NO
- Molecular weight
- 139.19 g/mol
- IUPAC name
- (1R,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-one
- SMILES
- CN1[C@@H]2CC[C@H]1CC(=O)C2
- InChIKey
- QQXLDOJGLXJCSE-KNVOCYPGSA-N
- XLogP
- 0.3
- Polar surface area
- 20.3 Ų
- H-bond donors
- 0
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
~4 min read
Article
9 sectionsContents
- Synthesis
- Robinson's "double Mannich" reaction
- Reaction mechanism
- From cycloheptanone
- Biochemistry method
- Reduction of tropinone
- See also
- References
- External links
Tropinone is an alkaloid, famously synthesised in 1917 by Robert Robinson as a synthetic precursor to atropine, a scarce commodity during World War I. Tropinone and the alkaloids cocaine and atropine all share the same tropane core structure. Its corresponding conjugate acid at pH 7.3 major species is known as tropiniumone.
==Synthesis==