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| Tropinone Basic information |
| Tropinone Chemical Properties |
| Tropinone Usage And Synthesis |
| Chemical Properties | Tropinone is a white to light yellow crystal powder, It is an alkaloid and a precursor to a number of additional plant alkaloids. Tropinone is the first intermediate in the biosynthesis of the pharmacologically important tropane alkaloids that possesses the 8-azabicyclo[3.2.1]octane core bicyclic structure that defines this alkaloid class. Chemical synthesis of tropinone was achieved in 1901 but the mechanism of tropinone biosynthesis has remained elusive. | | Uses | Tropinone is an oxidative product of Tropane, used to synthesize Morphine and Tropane alkaloids. | | Preparation | The first synthesis of tropinone was by Richard Willstätter in 1901. It started from the seemingly related cycloheptanone, but required many steps and had an overall yield of only 0.75%.Willstätter had previously synthesized cocaine from tropinone, in what was the first synthesis and elucidation of the structure of cocaine.
The 1917 synthesis by Robinson is considered a legend in total synthesis due to its simplicity and biomimetic approach. Tropinone is a bicyclic molecule, but the reactants used in its preparation are fairly simple: succinaldehyde, methyl amine and acetone dicarboxylic acid (or even acetone). The synthesis is a good example of a biomimetic reaction or biogenetic-type synthesis because biosynthesis makes use of the same building blocks. It also demonstrates a tandem reaction in a one-pot synthesis. Furthermore the yield of the synthesis was 17% and with subsequent improvements exceeded 90%. |
| Tropinone Preparation Products And Raw materials |
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