4101. Flindersine

Nomenclature

CAS number: 523-64-8
2,6-Dihydro-2,2-dimethyl-5H-pyrano[3,2-c]quinolin-5-one; 2,2′-dimethyl-α-pyrano(5′,6′,3,4)-2(1H)-quinolone.
C14H13NO2; mol wt 227.26.
C 73.99%, H 5.77%, N 6.16%, O 14.08%.

Description and 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.

Chemical structure

Properties

Crystals from methanol, dec 185-186°. uv max (methanol): 235, 333, 350, 365 nm (log ε 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.

Derivative

N-Methylflindersine.
C15H15NO2; mol wt 241.29.
C 74.67%, H 6.27%, N 5.80%, O 13.26%.

Properties

Crystals from petr ether, mp 84°.

Derivative

Dihydroflindersine.
C14H15NO2; mol wt 229.27.
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 ε 4.44, 3.94, 3.96, 3.93).