Convenient Synthesis of (Z)-7- and (E)-9-dodecene-1-yl Acetate, Components of Some Lepidoptera Insect Sex Pheromone

Andreica, Adriana Maria; Gansca, Lucia; Ciotlaus, Irina; Oprean, Ioan

Adriana Maria Andreica, Lucia Gansca, Irina Ciotlaus, Ioan Oprean

Convenient Synthesis of (Z)-7- and (E)-9-dodecene-1-yl Acetate, Components of Some Lepidoptera Insect Sex Pheromone

Abstract:

Were developed new and practical synthesis of (Z)-7-dodecene-1-yl acetate and (E)-9-dodecene-1-yl acetate. The routes involve, as the key step, the use of the mercury derivative of the terminal-alkyne w-functionalised as intermediate. The synthesis of (Z)-7-dodecene-1-yl acetate was based on a C6+C2=C8 and C8+C4=C12 coupling scheme, starting from 1,6-hexane-diol. The first coupling reaction took place between 1-tert-butoxy-6-bromo-hexane and lithium acetylide-ethylendiamine complex obtaining 1-tert-butoxy-oct-7-yne, which is transformed in di[tert-butoxy-oct-7-yne]mercury. The mercury derivative was directly lithiated and then alkylated with 1-bromobutane obtaining 1-tert-butoxy-dodec-7-yne. After acetylation and reduction with lithium aluminium hydride of 7-dodecyne-1-yl acetate gave (Z)-7-dodecene-1-yl acetate with 96 % purity. The synthesis of (E)-9-dodecene-1-yl acetate was based on a C8+C2=C10 and C10+C2=C12 coupling scheme, starting from 1,8-octane-diol. The first coupling reaction took place between 1-tert-butoxy-8-bromo-octane and lithium acetylide-ethylendiamine complex obtaining 1-tert-butoxy-dec-9-yne, which is transformed in di[tert-butoxy-dec-9-yne]mercury. The mercury derivative was directly lithiated and then alkylated with 1-bromoethane obtaining 1-tert-butoxy-dodec-9-yne. After reduction with lithium aluminium hydride of 1-tert-butoxy-(E)-9-dodecene and acetylation was obtained (E)-9-dodecene-1-yl acetate with 97 % purity.

Keywords:
(Z)-7-dodecene-1-yl acetate; (E)-9-dodecene-1-yl acetate; Lepidoptera; sex pheromone

Issue: 2017, Volume 68, Issue 1

Pages: 180-185

Publication date: 2017/2/15

https://doi.org/10.37358/RC.17.1.5415

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This article is published under the Creative Commons Attribution 4.0 International License

Citation Styles

Cite this article as:
ANDREICA, A.M., GANSCA, L., CIOTLAUS, I., OPREAN, I., Convenient Synthesis of (Z)-7- and (E)-9-dodecene-1-yl Acetate, Components of Some Lepidoptera Insect Sex Pheromone, Rev. Chim., 68(1), 2017, 180-185.

Vancouver
Andreica AM, Gansca L, Ciotlaus I, Oprean I. Convenient Synthesis of (Z)-7- and (E)-9-dodecene-1-yl Acetate, Components of Some Lepidoptera Insect Sex Pheromone. Rev. Chim.[internet]. 2017 Jan;68(1):180-185. Available from: https://doi.org/10.37358/RC.17.1.5415

APA 6th edition
Andreica, A.M., Gansca, L., Ciotlaus, I. & Oprean, I. (2017). Convenient Synthesis of (Z)-7- and (E)-9-dodecene-1-yl Acetate, Components of Some Lepidoptera Insect Sex Pheromone. Revista de Chimie, 68(1), 180-185. https://doi.org/10.37358/RC.17.1.5415

Harvard
Andreica, A.M., Gansca, L., Ciotlaus, I., Oprean, I. (2017). 'Convenient Synthesis of (Z)-7- and (E)-9-dodecene-1-yl Acetate, Components of Some Lepidoptera Insect Sex Pheromone', Revista de Chimie, 68(1), pp. 180-185. https://doi.org/10.37358/RC.17.1.5415

IEEE
A.M. Andreica, L. Gansca, I. Ciotlaus, I. Oprean, "Convenient Synthesis of (Z)-7- and (E)-9-dodecene-1-yl Acetate, Components of Some Lepidoptera Insect Sex Pheromone". Revista de Chimie, vol. 68, no. 1, pp. 180-185, 2017. [online]. https://doi.org/10.37358/RC.17.1.5415

Text
Adriana Maria Andreica, Lucia Gansca, Irina Ciotlaus, Ioan Oprean,
Convenient Synthesis of (Z)-7- and (E)-9-dodecene-1-yl Acetate, Components of Some Lepidoptera Insect Sex Pheromone,
Revista de Chimie,
Volume 68, Issue 1,
2017,
Pages 180-185,
ISSN 2668-8212,
https://doi.org/10.37358/RC.17.1.5415.
(https://revistadechimie.ro/Articles.asp?ID=5415)
Keywords: (Z)-7-dodecene-1-yl acetate; (E)-9-dodecene-1-yl acetate; Lepidoptera; sex pheromone

RIS
TY - JOUR
T1 - Convenient Synthesis of (Z)-7- and (E)-9-dodecene-1-yl Acetate, Components of Some Lepidoptera Insect Sex Pheromone
A1 - Andreica, Adriana Maria
A2 - Gansca, Lucia
A3 - Ciotlaus, Irina
A4 - Oprean, Ioan
JF - Revista de Chimie
JO - Rev. Chim.
PB - Revista de Chimie SRL
SN - 2668-8212
Y1 - 2017
VL - 68
IS - 1
SP - 180
EP - 185
UR - https://doi.org/10.37358/RC.17.1.5415
KW - (Z)-7-dodecene-1-yl acetate
KW - (E)-9-dodecene-1-yl acetate
KW - Lepidoptera
KW - sex pheromone
ER -

BibTex
@article{RevCh2017P180,
author = {Andreica Adriana Maria and Gansca Lucia and Ciotlaus Irina and Oprean Ioan},
title = {Convenient Synthesis of (Z)-7- and (E)-9-dodecene-1-yl Acetate, Components of Some Lepidoptera Insect Sex Pheromone},
journal = {Revista de Chimie},
volume = {68},
number = {1},
pages = {180-185},
year = {2017},
issn = {2668-8212},
doi = {https://doi.org/10.37358/RC.17.1.5415},
url = {https://revistadechimie.ro/Articles.asp?ID=5415}
}

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