| Identification | Back Directory | [Name]
(-)-3,9-Dihydro-2,3,3,9-tetramethylfuro[2,3-b]quinoline-4(2H)-one | [CAS]
31520-95-3 | [Synonyms]
Ifflaiamine
(-)-3,9-Dihydro-2,3,3,9-tetramethylfuro[2,3-b]quinolin-4(2H)-one
(-)-3,9-Dihydro-2,3,3,9-tetramethylfuro[2,3-b]quinoline-4(2H)-one
(-)-3,9-Dihydro-2,3,3,9-tetramethylfuro[2,3-b]quinoline-4(2H)-one
Furo[2,3-b]quinolin-4(2H)-one, 3,9-dihydro-2,3,3,9-tetramethyl-, (-)- | [Molecular Formula]
C15H17NO2 | [MOL File]
31520-95-3.mol | [Molecular Weight]
243.3 |
| Hazard Information | Back Directory | [Description]
This furanoquinoline alkaloid has been obtained from the bark of the Australian
tree Flindersia ifflaiana. It is obtained in the form of a colourless gum which
cannot be crystallized. The alkaloid is laevorotatory with [α]29D~~9 - 0.6° or
[α]29D~~o - 3.6° (c 8.0, MeOH). From aqueous solvents, a crystalline hydrate is
formed, m.p. 62-3°C. The ultraviolet spectrum in MeOH shows absorption
maxima at 215, 236, 309 and 320 mil with a shoulder at 251 and an inflexion at
298 mil. A yellow crystalline picrate is known, m.p. 207-9°C. The probable
structure obtained from infrared and NMR spectra, and dependent upon analogy with other alkaloids of this type, has been confirmed by the total synthesis of
the (±)-form, m.p. 128-9°C. | [References]
Bosson et al., Austral. 1. Chem., 16, 480 (1963)
Total syn thesis:
Chamberlain, Grundon., Tetrahedron Lett., 3547 (1967) |
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