Title: Flindersine
CAS Registry Number: 523-64-8
CAS Name: 2,6-Dihydro-2,2-dimethyl-5H-pyrano[3,2-c]quinolin-5-one
Additional Names: 2,2¢-dimethyl-a-pyrano(5¢,6¢,3,4)-2(1H)-quinolone
Molecular Formula: C14H13NO2
Molecular Weight: 227.26
Percent Composition: C 73.99%, H 5.77%, N 6.16%, O 14.08%
Literature References: From wood of Flindersia australis R. Br., Rutaceae: Matthes, Schreiber, Ber. Dtsch. Pharm. Ges. 24, 385 (1914). Structure: Brown et al., Aust. J. Chem. 7, 348 (1954). Synthesis: eidem, ibid. 9, 277 (1956); Piozzi et al., Gazz. Chim. Ital. 99, 711 (1969); Bowman et al., Chem. Commun. 1970, 666; Huffman, Hsu, Tetrahedron Lett. 1972, 141.
Properties: Crystals from methanol, dec 185-186°. uv max (methanol): 235, 333, 350, 365 nm (log e 4.42, 4.00, 4.10, 3.93). Sol in alc, benzene, chloroform, glacial acetic acid, paraffin, fatty oils, alkali hydroxides, slightly sol in petr ether. Practically insol in water.
Absorption maximum: uv max (methanol): 235, 333, 350, 365 nm (log e 4.42, 4.00, 4.10, 3.93)
Derivative Type: N-Methylflindersine
Molecular Formula: C15H15NO2
Molecular Weight: 241.29
Percent Composition: C 74.67%, H 6.27%, N 5.80%, O 13.26%
Properties: Crystals from petr ether, mp 84°.
Melting point: mp 84°
Derivative Type: Dihydroflindersine
Molecular Formula: C14H15NO2
Molecular Weight: 229.27
Percent Composition: C 73.34%, H 6.59%, N 6.11%, O 13.96%
Properties: Hexagons from ethyl acetate, mp 229°. uv max (methanol): 225, 272, 283, 312 nm (log e 4.44, 3.94, 3.96, 3.93).
Melting point: mp 229°
Absorption maximum: uv max (methanol): 225, 272, 283, 312 nm (log e 4.44, 3.94, 3.96, 3.93)
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