Ferrugine

(+)-Ferrugine
Identifiers
  • (8-methyl-8-azabicyclo[3.2.1]octan-2-yl)-phenylmethanone
CAS Number
PubChem CID
ChemSpider
Chemical and physical data
FormulaC15H19NO
Molar mass229.323 g·mol−1
3D model (JSmol)
  • C(=O)([C@@H]1[C@]2(N(C)[C@@](CC1)(CC2)[H])[H])C3=CC=CC=C3
  • InChI=1S/C15H19NO/c1-16-12-7-9-13(14(16)10-8-12)15(17)11-5-3-2-4-6-11/h2-6,12-14H,7-10H2,1H3/t12-,13-,14-/m0/s1
  • Key:FKBXXVPBVMWIDS-IHRRRGAJSA-N

Ferrugine (2α-benzoyltropane) is a tropane alkaloid discovered in the basic extract of the Australian rainforest tree Darlingia ferruginea where it occurs in the leaves and stems. The structure has been determined through spectroscopic analysis and confirmed by chemical synthesis.

(+)-Ferrugine is the natural enantiomer, with a reported specific rotation of ° (CHCl3).

See also

References

  1. ↑ Bick IC, Gillard JW, Woodruff M (1975). "Ferrugine. Novel tropane alkaloid". Chemistry & Industry (18). London, United Kingdom: 794..
  2. 1 2 Bick I, Gillard J, Leow H (1979). "Alkaloids of Darlingia ferruginea". Australian Journal of Chemistry. 32 (11): 2537. doi:10.1071/CH9792537.
  3. ↑ Ahmed S, Baker LA, Grainger RS, Innocenti P, Quevedo CE (October 2008). "Thermal elimination of diethyldithiocarbamates and application in the synthesis of (+/-)-ferrugine". The Journal of Organic Chemistry. 73 (20): 8116–8119. doi:10.1021/jo801652x. PMID 18785775.
  4. ↑ Ahmed S (August 2009). Total synthesis of ferrugine and synthetic studies towards ferrugine and stemofoline (Ph.D. thesis). University of Birmingham.
  5. ↑ Lazny R, Sienkiewicz M, Olenski T, Urbanczyk-Lipkowska Z, Kalicki P (September 2012). "Approaches to the enantioselective synthesis of ferrugine and its analogues". Tetrahedron. 68 (39): 8236–8244. doi:10.1016/j.tet.2012.07.061.