70224-30-5Relevant academic research and scientific papers
Trogoderma granarium sex pheromone and preparation method thereof
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, (2019/02/17)
The invention discloses trogoderma granarium sex pheromone and a preparation method thereof. The preparation method comprises the following steps: enabling (R)-2-methylbutanol to react with 5-sulfydryl-1-phenyltetrazole Mitsnobu to obtain A; enabling A to react with peroxy acid to obtain B; enabling 1,3-propanediol to react with benzyl chloride under an alkaline condition to obtain C; oxidizing Cto obtain a compound D; enabling B to react with D and hexamethyldisilamine lithium salt to obtain E; catalytically hydrogenating E by virtue of palladium to obtain F; enabling F, iodine, tertiary phosphine and imidazole to obtain G; obtaining H by using 1,8-octylene glycol and benzyl chloride and alkali; oxidizing H to obtain I; obtaining J by using I, carbon tetrabromide and triphenylphosphine Corey-Fush; obtaining K by using J and strong alkali; obtaining L by using K and G and alkali; obtaining M by using L, ethyl mercaptan and boron trifluoride diethyl etherate solution; catalytically hydrogenating M by virtue of metal to obtain N; and oxidizing N to obtain a target product, wherein a chemical name of the target product is (R,Z)-14-methylhexadeca-8-ene-1-aldehyde, thus obtaining the trogoderma granarium sex pheromone. The preparation method disclosed by the invention is low in cost and high in yield.
Pheromone synthesis. Part 240: Cross-metathesis with Grubbs I (but not Grubbs II) catalyst for the synthesis of (R)-trogodermal (14-methyl-8-hexadecenal) to study the optical rotatory powers of compounds with a terminal sec-butyl group
Mori, Kenji
experimental part, p. 3900 - 3909 (2009/09/08)
(R)-Trogodermal (14-methyl-8-hexadecenal), the sex pheromone of Trogoderma species of pest insects against stored products, and its (S)-isomer were synthesized by using olefin cross-metathesis between (R)- or (S)-7-methyl-1-nonene and 8-nonenyl acetate as the key step. This step was successful with Grubbs I but not with Grubbs II catalyst. The latter caused randomization of the carbon skeleton to give a mixture of abnormal products with both longer or shorter carbon chains than the desired product. The specific rotations of 18 newly and 6 previously synthesized compounds with a terminal sec-butyl group were measured to conclude them to be [α]D +3.5 to +6.5 or -3.6 to -6.4.
A Practical Synthesis of the Khapra Beetle Pheromones
Pawar, Archana S.,Chattopadhyay, Subrata,Mamdapur, Vasant R.
, p. 445 - 446 (2007/10/02)
A practical synthesis of the title pheromones is described.The features of the synthesis include high optical purities of the target compounds, utilization of easy accessible materials and employment of operationally simple and facile reactions.Key Words: Khapra beetle / Pheromones / Trogoderma granarium / 8-Hexadecenal, (14R)-14-methyl-
GLYCALS IN STEREOCHEMICAL SYNTHESIS SYNTHESIS OF (14R,8Z)-TROGODERMAL AND ITS (14S,8Z)-ENANTIOMER FROM DI-O-BENZOYL-D- AND -L-ARABINALS
Tolstikov, A. G.,Khakhalina, N. V.,Savateeva, E. E.,Spirikhin, L. V.,Odinokov, V. N.,Tolstikov, G. A.
, p. 624 - 628 (2007/10/02)
Enantiomerically pure (14R)-14-methylhexadeca-8Z-enal (cis-trogodermal) - the aggregation pheromone of the khapra beetle (Trogoderma) - and its (14S,8Z)-enantiomer has been effected from di-O-benzoyl-D- and -L-arabinals.
Chiral Synthesis of Trogodermal, the Pheromone of Dermestid Beetles
Chattopadhyay, S.,Mamdapur, V.R.,Chadha, M.S.
, p. 825 - 837 (2007/10/02)
The title pheromone, (R)-14-methyl-8-(Z and E)-hexadecen-1-al (Ia and Ib) have been synthesised following a simple route using (R)-pulegone as the starting chiron.
Pheromones, 67. - Synthesis of the Enantiomers of (Z)-14-Methyl-8-hexadecenal , the Pheromone of Some Trogoderma Species (Coleoptera: Dermestidae)
Bestmann, Hans Juergen,Frighetto, Rosa T. S.,Frighetto, Nelson,Vostrowsky, Otto
, p. 877 - 880 (2007/10/02)
The separation of diastereomeric phenylglycinolamides of 2-methylbutyric acid by means of MPLC yields the pure enantiomers of the acid, from which (R,Z)- and (S,Z)-14-methyl-8-hexadecenal (1) (trogodermal) can be obtained.
A STEREOCONTROLLED SYNTHESIS OF (R,Z)- AND (R,E)-14-METHYL-8-HEXADECENALS (TROGODERMAL), THE SEX PHEROMONES OF TROGODERMA SPECIES
Sato, Toshio,Naruse, Kouichi,Fujisawa, Tamotsu
, p. 3587 - 3590 (2007/10/02)
A stereocontrolled synthesis of (R,Z)- and (R,E)-14-methyl-8-hexadecenals with high stereochemical purity in both absolute and geometrical configurations was achieved by the use of the SN2 type ring-opening reaction of (S)-β-methyl-β-propiolact
