Tropinone

• 8-methyl -8 -azabicyclo [ 3.2.1] octan-3 -one ( IUPAC)
• 3- tropinone
• Tropane -3-one

(colorless crystal platelets, white crystalline powder ), trading as pale brown solid

Stimulant

1.9872 g · cm -3 ( 100 ° C)

41-44 ° C

227 ° C.

Poorly in water

1.4598 (100 ° C)

Template: Infobox chemical / molecular formula search available

Tropinone is a synthetic alkaloid with a tropane core structure that is also found in naturally occurring alkaloids such as cocaine and atropine.

Synthesis

The first synthesis of tropinone was carried out by Richard Willstätter in 1901. Suitable starting material he used the seemingly related Cycloheptanone over which he then in several steps Tropinone produced, but only with a yield of 0.75%. Willstätter had previously synthesized first cocaine from tropinone, which gave insight into the chemical structure of cocaine.

The first total synthesis was carried out in 1917 by Robert Robinson. Tropinone is a bicyclic molecule by the starting materials succinaldehyde, methylamine, and acetone dicarboxylic acid (or acetone only ) easy to make. This synthesis is a good example of a biomimetic reaction. It is also an example of a tandem - reaction in a one-pot reaction. The yield of this synthesis was 17% and was able to further improvements ( Clemens Schoepf, 1935) are increased to about 90%.

Reaction mechanism

The reaction mechanism can be divided into six steps are divided: