479409-91-1Relevant academic research and scientific papers
A novel group of allenic hydrocarbons from five Australian (Melolonthine) beetles
Fletcher,McGrath,Koenig,Moore,Cribb,Allsopp,Kitching
, p. 885 - 886 (2001)
Allenic hydrocarbons, previously unknown as a molecular class from insects, are represented by CH3(CH2)n-CH=?=CH-(CH2) 7CH3 (n = 11-15, 17, 19) in several Australian melolonthine scarab beetles and with demonstrated (R)-chirality when n = 11 and 13.
A suite of novel allenes from Australian melolonthine scarab beetles. Structure, synthesis, and stereochemistry
McGrath, Matthew J.,Fletcher, Mary T.,Koenig, Wilfried A.,Moore, Christopher J.,Cribb, Bronwen W.,Allsopp, Peter G.,Kitching, William
, p. 3739 - 3748 (2007/10/03)
A suite of allenic hydrocarbons, previously unknown as a molecular class from insects, has been characterized from several Australian melolonthine scarab beetles. The allenes are represented by the formula CH3(CH2)nCH=·=CH (CH2)7CH3 with n being 11-15, 17 and 19, and thus, all have Δ9,10-unsaturation. These structures have been confirmed by syntheses and comparisons of spectral and chromatographic properties with those of the natural components. The enantiomers of (±) Δ9,10-tricosadiene and Δ9,10-pentacosadiene were separable on a modified β-cyclodextrin column (gas chromatography), and the natural Δ9,10-tricosadiene (n = 11) and Δ9,10-pentacosadiene (n = 13) were shown to be of >85% ee. Syntheses of nonracemic allenes of known predominating chirality were acquired using both organotin chemistry and sulfonylhydrazine intermediates, and comparisons then demonstrated that the natural allenes were predominantly (R)-configured.
