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« Previous Compounddimethylfuran lactone    Next Compound »drimane-8alpha,11-diol
 
Compound - disparlure
 


Bedoukain

 
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cis-7,8-Epoxy-2-methyloctadecane
cis-7,8-Epoxy-2-methyloctadecane

Formula: C19H38O 
CAS#: 29804-22-6 
MW: 282.51 

[MS]  [ NMR ]  [Behavioural function]  [Chemdraw





Dots surface:


Reference(s) for synthesis of cis-7,8-Epoxy-2-methyloctadecane



Achmatowicz, O., Jr., and Sadownik, A. 1985. Stereoselective synthesis of both enantiomers of disparlure from D-glucose. J. Carbohydrate Chem. 4:435.
 
Achmatowicz, O., Jr., Sadownik, A., and Bielski, R. 1985. Stereoselective synthesis of both enantiomers of disparlure, the sex pheromone of the gypsy moth, from D-glucose. Polnish J. Chem. 52:553.
 
Bestmann, H.J., and Vostrowsky, O. 1974. Pheromone III. Eine stereoselektive synthese von 7,8-Z-epoxy-2-methyloctadecan, dem sexuallockstoff des schwammspinners (Lymantria dispar, Porthetria dispar. Lepidoptera). Tetrahedron Lett. 15:207-208.
 
Bestmann, H.J., Vostrowsky, O., and Stransky, W. 1976. Eine stereoselektive synthese des (Z)-7,8-epoxy-2-methyloctadecane (disparlure). Chem. Ber. 109:3375.
 
Bierl, B.A., Beroza, M., and Collier, C.W. 1970. Potent sex attactant of the gypsy moth: its isolation, identification and synthesis. Science. 70:87.
 
Bierl, B.A., Beroza, M., and Collier, C.W. 1972. Isolation, identification and synthesis of the gypsy moth sex attractant. J. Econ. Entomol. 65:659-664.
 
Botar, A.A., Oprean, B.I., Csonka-Horvai, J., and Hodosan, F. 1983. Exo- and endohormones. VI. Syntheses of the sex pheromones of some Lepidoptera. Rev. Roum. Chim. 28:741.
 
Brown, H.C., and Basavaiah, D. 1983. Pheromone synthesis via organoboranes: a convenient stereospecific synthesis of racemic disparlure, the sex pheromone of the gypsy moth (Porthetria dispar L.). Synthesis. 4:283-284.
 
Chan, T.H., and Chang, E. 1974. The synthesis of alkenes from carbonyl compounds and carbanions alpha to silicon. III. A full report and a synthesis of the sex pheromone of gypsy moth. J. Org. Chem. 39:3264-3268.
 
Chan, T.H., and Koumaglo, K. 1985. Silicon in organic synthesis. Stereoselective synthesis of some insect sex pheromones. J. Organomet. Chem. 285:109-120.
 
Duhl-Emswiler, B.A. 1979. A highly stereoselective synthesis of compounds related to (+)-disparlure, the sex attractant of the gypsy moth. Ph D. Dissertation, Michigan State University, East Lansing, MI.
 
Dzhemilev, U.M., Fakhretdinov, R.N., Telin, A.G., Tolstikov, G.A., Amirkhanov, D.V., and Krivonogov, V.P. 1981. A new approach to the synthesis of optically active disparlures - attractants of Porthetria dispar. Khim. Prir. Soedin. 650.
 
Eiter, K. 1972. Novel total synthesis of the sex attractant of Porthetria dispar (7,8-cis-epoxy-2-methyloctadecane). Angew. Chem. Int. Ed. Engl. 11:60-61.
 
Farnum, D.G., Veysoglu, T., Carde, A.M., Duhl-Emswiler, B., Pancoast, T.A., Reitz, T.J., and Carde, R.T. 1977. A stereospecific synthesis of (+)-disparlure, sex attractant of the gypsy moth. Tetrahedron Lett. 18:4009-4012.
 
Iwaki, S., Marumo, S., Saito, T., Yamada, M., and Katagiri, K. 1974. Synthesis and activity of optically active disparlure. J. Am. Chem. Soc. 96:7842-7844.
 
Joshi, N.N., Mamdapur, V.R., and Chadha, M.S. 1984. Synthesis of ()-disparlure & propylure: an efficient derivation from tetrahydrofurfuryl alcohol. Ind. J. Chem. 23B:231.
 
Kluenenberg, H., and Schaefer, H.J. 1978. Synthesis of disparlure by kolbe electrolysis. Angew. Chem. Int. Ed. Engl. 17:47-48.
 
Kost, A.N., Kovalev, B.G., Mateeva, E.D., Stan, V.V., Yudin, L.G., Elizarov, Ya., and Barybkina, M.N. 1977. Synthesis and biological activity of disparlure and its analogs. Bioorg. Khim. 3:934
 
Koumaglo, K., and Chan, T.H. 1984. Regioselection in the alkylation of trimethylsilylallyl anion - stereoselective synthesis of disubstituted alkenes. Tetrahedron Lett. 25:717-720.
 
Kovalev, B.G., Ishchenko, R.I., Marchenko, V.A., and Filippova, M.P. 1973. Synthetic studies on sexual attractants of insects. I. Synthesis of 2-methyl-7-octadecane oxide (disparlure) as a sexual attractant of an unpaired silkworm Porthetria dispar. Zh. Org. Khim. 9:6.
 
Kuepper, F.W., and Streck, R. 1975. Synthese von insektenpheromonen an metathesekatalysatoren. Chem. Zeit. 99:464.
 
Kuepper, F.W., and Streck, R. 1976. Synthese von insektenlockstoffen an metathesekatalysatoren. Z. Naturforsch. B. 31:1256.
 
Lin, G., Jiang, Y., and Zhou, W. 1985. Identification and synthesis of insect pheromones. XX. Synthesis of optically active sex pheromone of the gypsy moth from racemate by kinetic resolution of asymmetric epoxidation product. Huaxue Xuebao. 43:988.
 
Lin, G., Wu, B., Liu, L., Wang, X., and Zhou, W. 1984. Identification and syntheses of insect pheromones. XVI. Synthesis of the optically active sex pheromone of gypsy moth and its three optical isomers. Huaxue Xuebao. 42:797.
 
Markgraf, J.H., Lusskin, S.I., McDonald, E.C., and Volpp, B.D. 1983. Synthesis of ()-disparlure. J. Chem. Ecol. 9:211-218.
 
Marshall, J.A., Jablonowski, J.A., and Jiang, H. 1999. Total synthesis of the gypsy moth pheromones (+)- and (-)-disparlure from a single nonracemic alpha-silyloxy allylic stannane. J. Org. Chem. 64:2152-2154.
 
Masaki, Y., Serizawa, Y., Nagata, K., Oda, H., Nagashima, H., and Kaji, K. 1986. Synthesis of chiral 1,2-diols and related compounds of biological activities via stepwise ring fission of 5-alkyl-6,8-dioxabicyclo[3.2.1]octane skeleton. Tetrahedron Lett. 27:231-234.
 
Mori, K., and Ebata, T. 1981. Synthesis of optically active pheromones with an epoxy ring, (+)-disparlure and the saltmarsh caterpillar moth pheromone [(Z,Z)-3,6-cis-9,10-epoxyheneicosadiene]. Tetrahedron Lett. 22:4281-4282.
 
Mori, K., and Ebata, T. 1986. Syntheses of optically active pheromones with an epoxy ring, (+)-disparlure and both the enantiomers of (3Z,6Z)-cis-9,10-heneicosadiene. Tetrahedron. 42:3471-3478.
 
Mori, K., Takigawa, T., and Matsui, M. 1976. Stereoselective synthesis of optically active disparlure, the pheromone of the gypsy moth, Porthetria dispar. Tetrahedron Lett. 17:3953-3956.
 
Mori, K., Takigawa, T., and Matsui, M. 1979. Stereoselective synthesis of the both enantiomers of disparlure, the pheromone of the gypsy moth. Tetrahedron. 35:833-837.
 
Mychajlowskij, W., and Chan, T.H. 1976. The synthesis of alkenes from carbonyl compounds and carbanions alpha to silicon. V. Stereoselective synthesis of E- and Z-disubstituted alkenes. Tetrahedron Lett. 17:4439-4442.
 
Myrsina, R.A., and Semenyuk, N.L. 1975. Synthesis and physiological activity of some higher olefinic alcohols and their epoxy derivatives. Fiziol. Akt. Veshchestva. 7:127.
 
Niccoli, A., Conti, C., and Rossi, R. 1976. Feromoni chirali degli insetti - attivita biologica dello (Z)- ed (E)-8,9-epossi-(3S)-3-metilnonadecano, due analoghi strutturali del feromone sessuale della Lymantria dispar (L.). Chim. L'lnd. (Ital.). 58:877.
 
Odinokov, V.N., Balezina, G.G., Dzhemilev, U.M., Ishuratov, G.Yu., Amnirkhanov, D.V., Krivonogov, V.P., Sitnikova, F.Kh., and Tolstikov, G.A. 1982. Insect pheromones and their analogs., VIII. Synthesis of the (Z) and (E) isomers of 2-methyloctadec-7-ene and of 2-methyl-7,8-epoxyoctadecane. Khim. Prir. Soedin. 630.
 
Okada, K., Mori, K., and Matsui, M. 1977. A stereoselective synthesis of racemic (E)-7,8-epoxy-2-methyloctadecane, the geometrical isomer of racemic disparlure. Agric. Biol. Chem. 41:2485.
 
Pikul, W., Kozlowska, M., and Jurezak, J. 1987. Total synthesis of disparlure. Tetrahedron Lett. 28:2627-2628.
 
Pirkle, W.H., and Rinaldi, P.L. 1979. Synthesis and enantiomeric purity determination of the optically active epoxide disparlure, sex pheromone of the gypsy moth. J. Org. Chem. 44:1025-1028.
 
Rossi, R., and Conti, C. 1975. Gypsy moth sex attractant analogs. Synthesis of racemic (E)-7,8-epoxy-2-methyloctadecane and of (E) and (Z)-8,9-epoxy-(3S)-3-methylnonadecane. Chim. Ind. (Milano). 57:581.
 
Rossi, R., and Niccoli, A. 1977. Insect pheromones. Synthesis and biological activity of racemic (Z) and (E)-7,8-epoxy-2-methyloctadecane and of diastereoisomeric mixtures of (Z) and (E)-8,9-epoxy-(3S)-3-methylnonadecane towards Lymantria dispar L. and Lymantria monacha L. Redia. 60:507-524.
 
Sarmiento, R., Beroza, M., Bierl, B.A., and Tardif, J.G.R. 1972. Activity of compounds related to disparlure the sex attractant of the gypsy moth. J. Econ. Entomol. 65:665.
 
Shamshurin, A.A., Rekhter, M.A., and Vlad, L.A. 1973. Chemistry of pheromones: II. New synthesis of disparlure a sex attractant of the gypsy moth. Khim. Prir. Soedin. 545.
 
Sheads, R.E., and Beroza, M. 1973. Preparation of tritium-labeled disparlure, the sex attractant of the gypsy moth. J. Agric. Food Chem. 21:751-753.
 
Sheads, R.E., Beroza, M., and Paszek, E.C. 1975. Chemicals related to the gypsy moth sex pheromone as attractants and as synergists or inhibitors of the pheromone. J. Agric. Food Chem. 23:60-64.
 
Sonnet, P.E. 1978. Conversion of enoxides to olefins with trifluoroacetyl iodide and sodium iodide. J. Org. Chem. 43:1841-1842.
 
Sonnet, P.E., and Oliver, J.E. 1976. Olefin inversion. I. Reaction of aliphatic epoxides with triphenylphosphine dihalides. J. Org. Chem. 41:3279-3283.
 
Sonnet, P.E., and Oliver, J.E. 1976. Olefin inversion. II. Sodium iodide reductions of vic-bromochlorides and vic-dichlorides. J. Org. Chem. 41:3284-3286.
 
Subramanian, G.B.V., Chander, Y., and Sood, R.C. 1982. Synthesis of ()-trans-9,10-epoxy-2-methyloctadecane, an analogue of the gypsy moth pheromone (disparlure) & related epoxides. Ind. J. Chem. 21B:414.
 
Tolstikov, G.A., Dzhemilev, U.M., Balezina, G.G., and Krivonogov, V.P. 1978. Insect pheromones and their analogs. II. Synthesis of the sexual attractant of an unmated silkwsorm racemic dl disparlure. Khim. Prir. Soedin. 792.
 
Tsuboi, S., Furutani, H., Utaka, M., and Takeda, A. 1987. A practical synthesis of chiral 3-chloro-2-hydroxyalkanoates and 2,3-epoxyalcohols. Tetrahedron Lett. 28:2709-2712.
 
Vig, O.P., Sharma, M.L., Kumari, S., and Vohra, N. 1985. A new synthesis of (Z)-7,8-epoxy-2-methyloctadecane (disparlure). Ind. J. Chem. B. 24:860-861.
 
Wang, K.K., and Chu, K.-H. 1984. Preparation of (Z)-alkenes, ketones and alkynes via trialkyltin chloride induced intramolecular transfer reaction of Lithium 1-alkynyltrialkylborates. Stereoselective synthesis of the sex pheromones of the Douglas fir tussock moth, the gypsy moth, and the wild silkmoth Antheraea polyphemus. J. Org. Chem. 49:5175-5178.
 
Zavizion, L.P., Zubov, P.A., Verzunova, L.I., Chalova, Z.I., Shkolina, L.A., and Pyatnova, Y.B. 1980. Synthesis and biological activity of disparlure, gypsy moth attractant. Khim. Sredsiva. Zashchity Rast. 14.
 

 
Citation: El-Sayed AM 2014. The Pherobase: Database of Insect Pheromones and Semiochemicals. <http://www.pherobase.com>.
2003-2014 The Pherobase - Extensive Database of Insect Pheromones and Semiochemicals. Ashraf M. El-Sayed.
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