53353-01-8Relevant articles and documents
New syntheses of 1,7-dimethylnonyl propanoate, the western corn rootworm pheromone, in four different ways via cross metathesis, alkylation and coupling reactionsss
Mori, Kenji
experimental part, p. 595 - 600 (2011/04/23)
A mixture of the four stereoisomers of 1,7-dimethylnonyl propanoate, the female sex pheromone of the western corn rootworm (Diabrotica virgifera virgifera LeConte), was synthesized in four different ways by employing one of the following four reactions as the key step: (i) cross metathesis using the Grubbs I catalyst, (ii) cross metathesis using the Grubbs II catalyst, (iii) alkylation of an alkynide anion, and (iv) Grignard coupling in the presence of dilithium tetrachlorocuprate. Although the cross metathesis approaches enabled two short syntheses (4 or 6 steps) of the pheromone to be achieved, the cheapest and most efficient synthesis was possible via Grignard coupling to give the desired pheromone in a 40% overall yield based on 2-methyl-1-butanol (8 steps).
48. Ferroelectric Liquid Crystals Part 2 Chiral Phenyl Benzoates Incorporating a trans-1,4-Disubstituted Cyclohexane Ring
Kelly, Stephen M.,Buchecker, Richard
, p. 451 - 460 (2007/10/02)
About forty novel phenyl benzoates also incorporating a trans-1,4-disubstituted cyclohexane ring and a chiral centre have been prepared.The dependence of the liquid-crystal transition temperatures of this new class of compounds on lateral substituents, diverse central linkages, chain lengths, and position of the chiral centre has been studied systematically.The synthesis and liquid-crystal transition temperatures of these new compounds are described in detail.
SYNTHESIS AND BIOLOGICAL ACTIVITY OF BOTH (E)- AND (Z)-ISOMERS OF OPTICALLY PURE (S)-14-METHYL-8-HEXADECENAL (TROGODERMAL), THE ANTIPODES OF THE PHEROMONE OF THE KHAPRA BEETLE
Mori, K.,Kuwahara, S.,Levinson, H. Z.,Levinson, A. R.
, p. 2291 - 2297 (2007/10/02)
Both (E)- and (Z)-isomers of (S)-14-methyl-8-hexadecenal (trogodermal) were synthesized from 100percent optically pure (R)-(+)-citronellic acid.These antipodes of the khapra beetle pheromone were 1/500 to 1/1000 times as active as the natural (R)-pheromone.Determination of the optical purities of citronellic acid and related compounds was achieved by hplc method.Warning was made not to forget the measurement of density in expressing the optical rotation of a neat liquid as D (neat).