9581. Tremetone

Nomenclature

CAS number: 4976-25-4
1-[2,3-Dihydro-2-(1-methylethenyl)-5-benzofuranyl]ethanone; 2,3-dihydro-2-isopropenyl-5-benzofuranyl methyl ketone; 2-isopropenyl-2,3-dihydro-5-acetylbenzofuran.
C13H14O2; mol wt 202.25.
C 77.20%, H 6.98%, O 15.82%.

Description and references

Principal ketone suspected of being the active toxin of Eupatorium urticaefolium Reichard, Compositae (white snakeroot). Isoln and structure: Bonner, DeGraw, Tetrahedron 18, 1295 (1962). Synthesis of dihydrotremetone: DeGraw, Bonner, ibid. 1311. Synthesis of racemic tremetone: DeGraw et al., ibid. 19, 19 (1963); Bohlmann, Buehmann, Ber. 105, 863 (1972). Abs config: Bonner et al., Tetrahedron 20, 1419 (1964). Review: Christensen, Econ. Bot. 19, 293-300 (1965).

Chemical structure

Properties

Liquid. [α]D28 59.6° (c = 5.52 in absolute ethanol). nD25 1.5658. d428 1.080. uv max (ethanol): 227, 280, 285 nm (ε 11,950, 12,600, 12,300).

Derivative

Dihydrotremetone.

Nomenclature

(R)-1-[2,3-Dihydro-2-(1-methylethyl)-5-benzofuranyl]ethanone.
C13H16O2; mol wt 204.26.
C 76.44%, H 7.90%, O 15.67%.

Properties

Liquid. bp 216-221°. [α]D25 47.0° (c = 1.78 in abs ethanol). uv max (ethanol): 231, 279 nm (ε 39,500; 18,800).