Pseudopelletierine

Pseudopelletierine
Names
IUPAC name
9-Methyl-9-azabicyclo[3.3.1]nonan-3-one
Other names
Pseudopunicine; Granatonine; Pseudopelletrierin; Granatan-3-one; Pseudopelletierin; psi-Pelletierine; 9-Methyl-3-granatanone
Identifiers
3D model (JSmol)
ChEBI
ECHA InfoCard 100.008.202 Edit this at Wikidata
UNII
  • CN1C2CCCC1CC(=O)C2
Properties
C9H15NO
Molar mass 153.225 g·mol−1
Appearance Colorless (yellows on exposure)
Melting point 54 °C (129 °F; 327 K)
Boiling point Sublimes at 40 °C (0.3 mmHg)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Pseudopelletierine is the main alkaloid derived from the root-bark of the pomegranate tree (Punica granatum), along with at least three other alkaloids: pelletierine, isopelletierine, and methylpelletierine (C9H17ON), which yield 1.8, 0.52, 0.01, and 0.20 grams per kilogram of raw bark.

It is a homolog of tropinone, and can be synthesized in a manner analogous to the classical Robinson tropinone synthesis, using glutaraldehyde (rather than succinaldehyde), acetonedicarboxylic acid, and methylammonium chloride.[1] It was the starting material for Willstätter's 10-step synthesis of cyclooctatetraene, which was achieved after oxidation and several Hoffman elimination steps.

References

  1. ^ Arthur C. Cope; Hugh L. Dryden Jr.; Charles F. Howell (1957). "Pseudopelletierine". Organic Syntheses. 37: 73. doi:10.15227/orgsyn.037.0073.
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