70144-70-6

Upstream product

• 50816-19-8 8-bromooctanol 
• 70200-38-3 (R)-7-methylnon-1-yne 
• 74111-65-2 (R)-5-methylheptanoic acid 
• 74057-28-6 (R)-1-chloro-4-methyl-hexane 
• 52745-93-4 (4R)-4-methylhexanoic acid 
• 55944-71-3 7-chloro-1-(tetrahydropyranyloxy)heptane 
• 130129-94-1 (R)-14-methylhexadec-8-yn-1-al dimethyl acetal 
• 127060-15-5 3-nonynal dimethyl acetal 
• 130129-92-9 7-hydroxyheptanal dimethyl acetal 
• 130129-93-0 7-bromoheptanal dimethyl acetal 
• 22054-13-3 7-hydroxyheptanal 
• 84231-08-3 (E)-(S)-15-[1,3]Dioxan-2-yl-3-methyl-pentadec-8-enoic acid 
• 84231-06-1 (E)-(S)-15-[1,3]Dioxan-2-yl-3-methyl-pentadec-8-en-1-ol 
• 84231-03-8 (E)-13,13-trimethylenedioxytridec-5-enyl chloride 

Relevant academic research and scientific papers

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

(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

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

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

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

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 STEREOCONTROLLED SYNTHESIS OF (R,Z)- AND (R,E)-14-METHYL-8-HEXADECENALS (TROGODERMAL), THE SEX PHEROMONES OF TROGODERMA SPECIES

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