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Compound - chalcogran [2-Ethyl-1,6-dioxaspiro[4.4]nonane]

Bedoukain RussellIPM
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Formula: C9H16O2 
CAS#: 38401-84-2 
MW: 156.22 

[MS]  [ NMR ]  [ Kovats ]  [Behavioural function

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Reference(s) for synthesis of 2-Ethyl-1,6-dioxaspiro[4.4]nonane [chalcogran]

Balea, A., Pojar-Fenesan, M., Pop, L. Oprean, I., and Ciupe, H. 2002. Exo and endohormones. XX1 Synthesis of racemic 2-ethyl-1,6-dioxaspiro[4,4] nonane, the aggregation pheromone of Pityogenes chalcographus (Coleoptera, Scolytidae). Rev. Roum. Chim. 47:465-469.
Cekovic, Z., Bosnjak, J., Mandic, D., and Ilijev, D. 1985. Synthesis of spiro-ketal pheromones. Croatica Chem. Acta. 58:671.
Doherty, A.M., Ley, S.V., Lygo, B., and Williams, D.J. 1984. Synthesis of spiroacetals using organoselenium-mediated cyclisation reactions. X-ray molecular structure of (2S,8R)-8-methyl-2-phenyl-1,7-dioxaspiro[5.5]undecan-4(R)-ol. J. Chem. Soc. Perkin Trans. 1:1371-1377.
Enders, D., Dahmen, W., Dederichs, E., and Weuster, P. 1983. Spiroacetals from acetone and oxiranes - a simple route to optically active 1,6-dioxaspiro[4.4]nonane-pheromones. Synth. Comm. 13:1235-1242.
Francke, W., and Reith, W. 1979. Alkyl-1,6-dioxaspiro[4.4]nonane, eine neue klasse von pheromonen. Liebigs Ann. Chem. 1.
Francke, W., Heemann, V., Gerken, B., Renwick, J.A.A., and Vite, J.P. 1977. 2-ethyl-1,6-dioxaspiro[4 4]nonane, principal aggregation pheromone of Pityogenes chalcographus (L.), Naturwissenschaften. 64:590.
Hungerbühler, E., Naef, R., Wasmuth, D., Seebach, D., Loosli, H.-R., and Wehrli, A. 1980. Synthese optisch aktiver 2-methyl- und 2-ethyl-1,6-dioxaspiro[4.4]nonan- und -[4.5]decan - pheromone aus einem gemeinsamen chiralen vorlaeufer. Helv. Chim. Acta. 63:1960-1970.
Ireland, R.E., and Haebich, D. 1981. Pheromonsynthesen - modellreaktionen zur synthese von polyether-antibiotika. Chem. Ber. 114:1418.
Koppenhoefer, B., Hintzer, K., Weber, R., and Schurig, V. 1980. Quantitative separation of the enantiomeric pairs of the pheromone 2-ethyl-1,6-dioxaspiro[4.4]nonane by complexation chromatography on an optically active metal complex. Angew. Chem. Int. Ed. Engl. 19:471-472.
Kozhich, O.A., Segal, G.M., and Torgov, I.V. 1982. Synthesis of 2-ethyl-1,6-dioxaspiro(4.4)nonane, main component of the chalcograph beetle (Pityogenes chalcographus L.) pheromone. Izv. Akad. Nauk. SSSR. Ser. Khim. 325.
Mori, K., Sasaki, M., Tamada, S., Suguro, T., and Masuda, S. 1979. Synthesis of optically active 2-ethyl-1,6-dioxaspiro[4.4]nonane (chalcogran), the principal aggregation pheromone of Pityogenes chalcographus (L.). Tetrahedron. 35:1601-1605.
Phillips, C., Jacobson, R., Abrahams, B., Williams, H.J., and Smith, L.R. 1980. Useful route to 1,6-dioxaspiro[4.4]nonane and 1,6-dioxaspiro[4.5]decane derivatives. J. Org. Chem. 45:1920-1924.
Redlich, H. 1982. Chirale bausteine aus kohlenhydraten, VI. Synthese von (2R,5RS)- und (2S,5RS)-2-ethyl-1,6-dioxaspiro[4.4]nonan (chalcogran) aus D-glucose. Liebigs Ann. Chem. 708.
Redlich, H., and Francke, W. 1980. Optically active chalcogran (2-ethyl-1,6-dioxaspiro[4.4]nonane). Angew. Chem. Int. Ed. Engl. 19:630-631.
Rosini, G., Ballini, R., Petrini, M., and Marotta, E. 1986. Nitromethane as d1,d1 multiple coupling reagent for the carbonyl dianion synthon. Practical synthesis of chalcogran. Angew. Chem. Int. Ed. Engl. 25:941-942.
Smith, L.R., Williams, H.J., and Silverstein, R.M. 1978. Facile synthesis of optically active 2-ethyl-1 6dioxaspiro[4.4]nonane, component of the aggregation pheromone of the beetle Pityogenes chalcographus (L.). Tetrahedron Lett. 19:3231-3232.
Utimoto, K. 1983. Palladium catalyzed synthesis of heterocycles. Pure Appl. Chem. 55:1845.

Citation: El-Sayed AM 2024. The Pherobase: Database of Pheromones and Semiochemicals. <>.
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