14-Methyl-8-hexadecenal

Structure elucidation of the female-produced sex pheromones of Trogo-derma spp. has a rather confused history. Extracts of females of T. inclusum were shown to contain (Z)-14-methyl-8-hexadecenol and the methyl ester of the respective carboxylic acid [215]. The corresponding compounds showing (E)-configuration were shown to be present and behaviourally active in T. inclusum [216]. Finally, investigations of head space collections, obtained with live females, revealed the presence of 14-methyl-8-hexadecenal, an aldehyde... 

Two of the sexual releasers secreted by females of Troqoderma inclusum have been identified as (ZJ-(-)-14-methyl-8-hexadecen-l-ol and (-)-methyl (Z)-14-methyl-8-hexadecenoate (57) Each of these compounds is active by itself and in addition, two unidentified pheromones are present in the sex attractant blend. The alcohol is attractive to five other species of Troqoderma, making it seem likely that similar compounds are utilized as sex pheromones by many species in this genus. Indeed, Yarger et al. (58) identified methyl ( )-14-methyl-8-hexadecenoate and (Ej-14-methyl-8-hexadecen-l-ol in extracts of females of X dlabrum. 

Cross, J.H., Byler, R.C., Cassidy, R.F. Jr, Silverstein, R.M., Greenblatt, R.E., Burkholder, W.E., Levinson, A.R. and Levinson, H.Z. (1976) Porapak-Q collection of pheromone components and isolation of (Z)- and (E)-14-methyl-8-hexadecenal, potent sex attracting components, from the frass of four species of Trogoderma (Coleoptera Dermestidae). Journal of Chemical Ecology 2, 457-468. 

Methylhexadecanoic acid, M-00064 14-Methyl-8-hexadecenal, M-00065 14-Methyl-8-hexadecenoic acid, M-00066 14-Methyl-8-hexadecen-1 -ol, M-00067 Methyl hydroperoxidooctadecatrienoates, see... 

Four species of Trogoderma beetles use methyl-branched alkenals as their major sex pheromones 300). Aeration of T. gramrium and trapping of the volatiles on Porapak Q gave a 92 8 ratio of (Z)- to ( )-14-methyl-8-hexadecenal. The Z-isomer was the major component obtained from T. inclusum and T. variabile and the -isomer was obtained from T. glabrum. In laboratory bioassays males could discriminate between the geometric isomers. 

Methyl-l-hexadecene and 4-t-butyl-l-methylenecycIohexane were obtained respectively in 85 and 73% yields. 

C17H34 2-methyl-1-hexadecene 61868-19-7 274.65 37.196 2 31055 C18H35Br tran s-1 -bromo-1 -octadecene 66292-45-3 346.84 47.863 2... 

C16H32 1-hexadecene 629-73-2 2.261 E- 10 167.070 31752 C19H40S methyl octadecyl sulfide 40289-98-3 2.849E+10 212.050... 

E/O co-polymerization reports with bis(cyclopentadienyl) complexes include ethylene/1-butene, ethylene/l-pentene,254 ethylene/4-methyl-l-pentene,516,522,523 ethylene/1-hexene,229,230,254,446,447,478,481,484,509,512-515, 517-519,522,524-530 ethyiene/1.octene(254,504,505,515,522,531-535 ethyiene/i decene,254,520 ethylene/1-dodecene,254,536 ethylene/1-tetradecene,254,532 ethylene/1-hexadecene,511,512,518,525 ethylene/1-octadecene.532,536... 

The silylated methyl ester was then a-methylated with lithium diisopropylamide and methyl iodide in tetrahydrofuran. Reduction of methyl 10-( erl-butyldimethylsilyloxy)-2-methyldecanoate with DIBAL in ether at -78°C afforded the corresponding aldehyde. The 10- tert-butyldimethylsilyloxy)-2-methyldecanal was subsequently coupled in a Wittig reaction with 1-hexyltriphenylphosphonium bromide and n-butyllithium affording (Z)- and ( )-1 -(teri-butyldimethylsilyloxy)-9-methyl-10-hexadecene in a 9 1 ratio, respectively. Deprotection with tetrabutylammonium fluroride (TBAF) in tetrahydrofuran and final oxidation with pyridinium dichromate (PDC) in dimethylformamide resulted in a 9 1 mixture of (Z)- and ( )-9-methyl-10-hexadecenoic acid as shown in Fig. (7). As was also the case with acid 6, the stereochemistry at C-9 in 7 is not known. The key step in the synthesis of the allylic methyl group was a-methylation of a methyl ester, followed by reduction to the corresponding aldehyde, which was used in the subsequent Wittig reaction. 

Hexadecene, (Z)-2-Hexadecene, ( )-2-Hexadecene, 2-methyl-2-Hexadecene, 14-methyl-, (Z)-... 

HEPTYL-2-CYCL0HEXEN0NE, 61, 59 1-Hexadecene, 60, 13 HEXAFLUOROACETONE, 63, 154 Hexafluoropropene, 63, 154 HEXAHYDR0-2-(lH)-AZ0ClN0NE, 63, 188 2,3,3a,4,7,7a-Hexahydro-3a-hydroxy-7a-methyl-IH-i ndene-... 

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