16695-35-5Relevant academic research and scientific papers
Preparation of Geometrical Isomers of 2,7-Dodecadienal, 2,7-Dodecadienyl Formate, and Other 1,6-Diene System-containing Compounds and Their Electroantennography Activities toward Male Eri-Silk Moths
Hatanaka, Akihiko,Ishii, Yasushige,Tomida, Ichiro
, p. 2036 - 2038 (2007/10/02)
We measured the electroantennography (EAG) activities of the geometrical isomers of several pheromone-related compounds towards male eri-silk moths (Samia cynthia richini) using EAG-gas chromatography (GC).C16-aldehyde and formyl ester, with the same chain length as C16-aldehyde, were found to be much more active than other compounds with a shorter chain.For the compounds with (1Z,6Z)- or (1E,6E)-configuration, the activity in decreasing order was C14-formyl ester > C16-aldehyde > C14-aldehyde > C12-formyl ester, while that for the compounds with (1Z,6E)- or (1E,6Z)-configuration is C16-aldehyde > C14-formyl ester > other compounds with a shorter C14 chain.
STEREOSPECIFIC SYNTHESIS OF COMPONENTS OF THE NATURAL SEX PHEROMONE OF Pectinophora gossypiella
Matveeva, E. D.,Kvasha, M. P.,Kurts, A.L.
, p. 1017 - 1021 (2007/10/02)
A multistage stereospecific synthesis of components of the natural pheromone was realized.Conditions were found for stereospecific trans-reduction of the triple bonds.A procedure was developed for regiospecific dehydrohalogenation of 1,2-dibromoalkanes.Conditions giving the Z and E isomers in ratio of 96 : 4 were found for the Wittig reaction.
STEREOSELECTIVE AND VERSATILE APPROACH FOR THE SYNTHESIS OF GOSSYPLURE AND ITS COMPONENTS
Joshi, N. N.,Mamdapur, V. R.,Chadha, M. S.
, p. 3285 - 3290 (2007/10/02)
Efficient synthetic routes to gossyplure and its components (1a and 1b) were formulated.The three key units viz the alkynol 3, the bromide 5, and the alkanal 13 were derived from easily accessible starting materials.Alkylation of 3 with 5, and subsequent semihydrogenation followed by oxidation, provided the C11-alkenal 8 which was subjected to a stereocontrolled Wittig reaction with a C5-phosphonium salt, to yield directly the disired pheromone (1a + 1b).The synthesis of its individual components involved the manipulation via an acetylenic intermediate, viz the alkynol 14 which was obtained through alkylation of 3.A sequence of well-established reactions on 14, then provided the corresponding (E)- and (Z)-alkenylphosphonium salts which upon a (Z)-specific Wittig olefination with the C7-aldehyde (13), led to the stereoselective synthesis of 1a and 1b.
A Convenient Synthesis of (E)-9-Tetradecen-1-yl Acetate, a Sex Pheromone of Gelechiid Moth and (E)-5-Decenol, a Sex Pheromone of Peach Twig Borer
Chattopadhyay, A.,Mamdapur, V. R.,Chadha, M. S.
, p. 1221 - 1223 (2007/10/02)
n-Butyllithium reacts with dihydropyran to give (E)-4-nonenyl alcohol (IV).The alcohol (IV) is converted into the corresponding bromide (V).The Grignard reagent of the bromide (V) on coupling with the bromide (VI) in the presence of Li2CuCl4, followed by hydrolysis yields the alcohol (III).This on acetylation gives the pheromone (I).The formylation of the Grignard reagent prepared from V gives the pheromone (II).
Carbon-Carbon Bond Formation by the Use of Chloroiodomethane as a C1 Unit. II. The Preparation and Synthetic Application of 1-Chloro-3-iodoheptane
Miyano, Sotaro,Hokari, Hiroshi,Umeda, Yoshiharu,Hashimoto, Harukichi
, p. 770 - 774 (2007/10/02)
Terminal alkenes, R-CH=CH2 (R=Et, n-Pr, n-Bu, N-Hex), were readily transformed into 1-chloro-3-iodoalkanes by the AIBN-induced free radical addition of chloroiodomethane.Thus, 1-chloro-3-iodoheptane was obtained from 1-hexene in an 88percent yield; this in turn was allowed to react with dialkyl malonates in the presence of alkoxides in alcohols to give dialkyl 2-butylcyclobutane-1,1-dicarboxylates and dialkyl (E)-3-octene-1,1-dicarboxylates (7), either of which could be obtained preferentially by the choice of the experimental parameters.The olefinic product, 7, was further utilized for the synthesis of (E)-5-decenyl acetate and/or 1,4-nonanolide.
