60609-52-1Relevant articles and documents
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.
Method of manufacturing [...]
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, (2019/08/20)
PROBLEM TO BE SOLVED: To provide a method of practically producing (Z)-14-methylhexadec-8-enal in total 5 processes using inexpensive octane-1,8-diol as a starting raw material and without using pyridinium chlorochromate or hexamethylphosphoric triamide.SOLUTION: A method of producing (Z)-14-methylhexadec-8-enal includes total 5 processed including a first process of monoacetylation of octane-1,8-diol as a starting raw material, a second process of oxidation, a third process of reacting phosphonium salt having a 6-methyloctyl group with ylide generated from a base, a fourth process of carrying out alcoholysis, and a fifth process of oxidation.
A practical total synthesis of both e - And Z -isomers of optically pure (S)-14-methylhexadec-8-enal (Trogodermal)
Yadav, Jhillu S.,Chandravathi,Thrimurtulu,Prasad,Ghamdi, Ahmad Alkhazim Al
, p. 1513 - 1518 (2013/07/05)
The total synthesis of both E- and Z-isomers of optically pure (S)-14-methylhexadec-8-enal (trogodermal) is described. Key steps involved Corey-Fuchs reaction, zipper isomerization, and different hydrogenation conditions for cis- and trans-isomers. Georg
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-
OZONOLYSIS OF ALKENES AND STUDY OF THE REACTIONS OF POLYFUNCTIONAL COMPOUNDS. L. SYNTHESIS OF (R,E)TROGODERMAL, AN AGGREGATION PHEROMONE OF THE BEETLE, Trogoderma granarium
Odinokov, V. N.,Ishmuratov, G. Yu.,Kharisov, R. Ya.,Serebryakov, E. P.,Tolstikov, G. A.
, p. 1286 - 1288 (2007/10/02)
A new synthesis is proposed for (R,E)-14-methyl-8-hexadecenal, which is an aggregation pheromone of the beetle, Trogoderma granarium, from available cyclooctene and (S)-(+)-3,7-dimethyl-1,6-octadiene (dihydromyrcene) using ozonolysis in two of the reaction steps.
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.
A facile synthesis of (S)-trogodermal
Chattopadhay, S.,Mamdapur, V. R.,Chadha, M. S.
, p. 848 - 849 (2007/10/02)
A simple route for the synthesis of (S)-(Z)- and (S)-(E)-14-methyloctadec-8-en-1-al (Ia and Ib) has been developed.The achiral acetylene (9) is alkylated with the chiron bromide (S)-5 in the presence of BuLi as the base to give 10.This on subsequent functionalisation furnishes both Ia and Ib.
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.
