Title: Tremetone
CAS Registry Number: 4976-25-4
CAS Name: 1-[2,3-Dihydro-2-(1-methylethenyl)-5-benzofuranyl]ethanone
Additional Names: 2,3-dihydro-2-isopropenyl-5-benzofuranyl methyl ketone; 2-isopropenyl-2,3-dihydro-5-acetylbenzofuran
Molecular Formula: C13H14O2
Molecular Weight: 202.25
Percent Composition: C 77.20%, H 6.98%, O 15.82%
Literature 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).
Properties: Liquid. [a]D28 -59.6° (c = 5.52 in absolute ethanol). nD25 1.5658. d428 1.080. uv max (ethanol): 227, 280, 285 nm (e 11,950, 12,600, 12,300).
Optical Rotation: [a]D28 -59.6° (c = 5.52 in absolute ethanol)
Index of refraction: nD25 1.5658
Absorption maximum: uv max (ethanol): 227, 280, 285 nm (e 11,950, 12,600, 12,300)
Density: d428 1.080
Derivative Type: Dihydrotremetone
Additional Names: (R)-1-[2,3-Dihydro-2-(1-methylethyl)-5-benzofuranyl]ethanone
Molecular Formula: C13H16O2
Molecular Weight: 204.26
Percent Composition: C 76.44%, H 7.90%, O 15.67%
Properties: Liquid. bp 216-221°. [a]D25 -47.0° (c = 1.78 in abs ethanol). uv max (ethanol): 231, 279 nm (e 39,500; 18,800).
Boiling point: bp 216-221°
Optical Rotation: [a]D25 -47.0° (c = 1.78 in abs ethanol)
Absorption maximum: uv max (ethanol): 231, 279 nm (e 39,500; 18,800)
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