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
CAS Number	552-70-5 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:8607 N
PubChem CID	11096
UNII	USN3FV3Z9X Y
SMILES CN1C2CCCC1CC(=O)C2
Properties
Chemical formula	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).
N verify (what is YN ?)
Infobox references

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

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