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[1][2] and confirmed by chemical synthesis.[3][4][5]

(+)-Ferrugine is the natural enantiomer, with a reported specific rotation of ° (CHCl3).[2]

See also

References

  1. ^ Bick IC, Gillard JW, Woodruff M (1975). "Ferrugine. Novel tropane alkaloid". Chemistry & Industry (18). London, United Kingdom: 794..
  2. ^ a b 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.
This article is issued from Wikipedia. The text is available under Creative Commons Attribution-Share Alike 4.0 unless otherwise noted. Additional terms may apply for the media files.