A Practical Synthesis of (Z)- and (E)-8-Dodecene-1-yl Acetate, Components of Lepidoptera Insect Sex Pheromones
| Autor: | Irina Ciotlaus, Adriana Maria Andreica, Lucia Gansca, Ioan Oprean |
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| Rok vydání: | 2017 |
| Předmět: |
Process equipment
Chemistry Materials Science (miscellaneous) Process Chemistry and Technology media_common.quotation_subject General Engineering General Chemistry General Medicine Insect General Biochemistry Genetics and Molecular Biology Lepidoptera genitalia Petrochemistry Sex pheromone Materials Chemistry Organic chemistry General Pharmacology Toxicology and Pharmaceutics media_common |
| Zdroj: | Revista de Chimie. 68:157-162 |
| ISSN: | 2668-8212 0034-7752 |
| DOI: | 10.37358/rc.17.1.5410 |
| Popis: | New and practical synthesis of (Z)-8-dodecene-1-yl acetate and (E)-8-dodecene-1-yl acetate were developed. The synthesis were based on a C3+C6=C9 and C9+C3=C12 coupling scheme, the starting material being 2-propyn-1-ol and 1,6-hexandiol. The routes involve, as the key step, the use of the same mercury derivative of the terminal-alkyne w-functionalised as intermediate. The first coupling reaction took place between methoxyallene and Grignard reagent of 1-tert-butoxy-6-bromo-hexan obtaining 1-tert-butoxy-non-8-yne, which is transformed in di[1-tert-butoxy-non-8-yne]mercury, the common intermediate in the synthesis of the two pheromones. In order to obtain (Z)-8-dodecene-1-yl acetate and (E)-8-dodecene-1-yl acetate, the mercury derivative was directly lithiated and then alkylated with 1-bromo-propan obtaining 1-tert-butoxy-dodec-8-yne. After acetylation of 1-tert-butoxy-dodec-8-yne and stereoselective reduction in the presence of NiP-2 catalyst gave (Z)-8-dodecene-1-yl acetate with 85 % isomeric purity. After reduction with lithium aluminium hydride of 1-tert-butoxy-dodec-8-yne and acetylation was obtained (E)-8-dodecene-1-yl acetate with 90% isomeric purity. |
| Databáze: | OpenAIRE |
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