51812-91-0

Usage

InChI:InChI=1/C19H36O2/c1-2-3-4-5-6-7-8-9-10-11-12-14-17-20-19-16-13-15-18-21-19/h5-6,19H,2-4,7-18H2,1H3/b6-5+

Upstream product

• 53963-10-3 2-[(6-bromohexyl)oxy]tetrahydro-2H-pyran 
• 53155-10-5 (E)-1-oct-3-enyl bromide 
• 19754-59-7 tetrahydro-2-(9-tetradecynyloxy)pyran 
• 50816-19-8 8-bromooctanol 
• 629-41-4 1,8-Octanediol 
• 50816-20-1 2-(8-bromooctyloxy)tetrahydropyran 
• 110-87-2 3,4-dihydro-2H-pyran 

Downstream Products

• 57491-35-7 3(Z),13(E)-octadecadien-1-yl acetate 
• 71655-21-5 C₂₃H₄₂O₂ 

Relevant academic research and scientific papers

Synthesis and characterization of 3,13- and 2,13-octadecadienyl compounds for identification of the sex pheromone secreted by a clearwing moth, Nokona pernix

Several geometrical isomers of 3,13- and 2,13-octadecadien-1-ols and their acetates were synthesized starting from 1,8-octanediol or 1,9-nonanediol utilizing acetylene coupling reactions. In addition to commercially available compounds, all geometrical isomers of each dienyl compound were analyzed by NMR and GC-MS to accumulate chemical data for studies of sex pheromones secreted from clearwing moths classified into the family Sesiidae of Lepidoptera. Although acetoxy derivatives of the 3,13- and 2,13-dienes showed almost the same mass spectra, the alcohols were distinguished by comparing the relative intensities of [M - 18]+ at m/z 248, indicating direct differentiation of the two positional isomers without derivatization. Furthermore, each geometrical isomer eluted from a high-polar GC column with a different retention time. Base on these data, a pheromone gland extract of a sesiid moth, Nokona pernix, was analyzed by GC-EAD and GC-MS, and two EAG-active components were identified, viz., the (3E,13Z)- and (3Z,13Z)-isomers of 3,13-octadecadien-1-ol in a ratio of 9:1. In the field, the synthetic compounds mixed in 9:1 ratio attracted N. pernix males well, while a single component scarcely attracted the males. The number of attracted males peaked in the middle of June, and a small second peak was observed in August.

STEREOSPECIFIC SYNTHESIS OF TRANSOID MONO- AND 1,3-DIENE PHEROMONES OF LEPIDOPTERA FROM SECONDARY CYCLOPROPYLCARBINOLS

The zinc halide-initiated homoallylic rearrangement of saturated or allylic cyclopropylcarbinols in the presence of trimethylsilyl halides has been employed as the key step in the total synthesis of seven behavioral regulators in twenty insects of the Lepidoptera family, namely 9E-tetradecenol and its acetate, 11E-hexadecenol and its acetate, 11E-hexadecenal, 5E,7E-dodecadienol, and 3E,5E-tetradecadienyl acetate.