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Compound - stegobinone

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2,3-Dihydro-2,3,5-trimethyl-6-(1-methyl-2-oxobutyl)-4H-pyran-4-one Formula:  C13H20O3  CAS#:    MW:  224.3  [MS]  [ NMR ]  [Behavioural function]  [Chemdraw]

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Reference(s) for synthesis of 2,3-Dihydro-2,3,5-trimethyl-6-(1-methyl-2-oxobutyl)-4H-pyran-4-one Ansell, J.M., Hassner, A., and Burkholder, W.E. 1979. The synthesis of the drugstore beetle pheromone (stegobinone). Tetrahedron Lett. 20:2497-2498.   Hoffmann, R.W., and Ladner, W. 1979. On the absolute stereochemistry of C-2 and C-3 in stegobinone. Tetrahedron Lett. 20:4653-4656.   Hoffmann, R.W., Ladner, W., Steinbach, K., Massa, W., Schmidt, R., and Snatzke, G. 1981. Stereoselektive synthese von alkoholen. IX. Absolut konfiguration von stegobinon. Chem. Ber. 114:2786.   Mori, K., Ebata, T., and Sakakibara, M. 1981. Synthesis of (2S,3R,7RS)-stegobinone [2,3-dihydro-2,3,5-trimethyl-6(1methyl)1-2-oxobutyl)-4H-pyran-4-one] and its (2R,3S,7RS)-isomer. Tetrahedron. 37:709-713.   Ono, M., Onishi, I., Kuwahara, Y., Chuman, T., and Kato, K. 1983. Synthesis of (±)-2,3-cis-stegobinone, (±)-cis-2,3dihydro-2,3,5trimethyl-6-(1-methyl-2-oxobutyl)-4-pyran-4-one, the sex pheromone of drugstore beetle. Agric. Biol. Chem. 47:1933.   Sakakibara, M. and Mori, K. 1979. Synthesis of a stereoisomeric mixture of 2,3-dihydro-2,3,5-trimethyl-6-(1-methyl-2oxo-butyl)-4H-pyran-4-one the pheromone of the drugstore beetle. Tetrahedron Lett. 20:2401-2402.   Sakakibara, M., Mori, K., and Seto, H. 1979. CMR study on 2,3-dihydro-2,3,5-trimethyl-6-(1-methyl-2-oxobutyl)-2H-pyran-4-one, the pheromone of the drugstore beetle conformation of 2,3-vic-dimethyl groups. Agric. Biol. Chem. 43:2203.