68820-32-6Relevant academic research and scientific papers
Synthesis and biological testing of ester pheromone analogues for two fruitworm moths (Carposinidae)
Barker, David,Chhagan, Asha,Park, Kye Chung,Pilkington, Lisa I.,Suckling, David M.,Twidle, Andrew M.
, p. 9557 - 9567 (2020/10/13)
A range of ester pheromone analogues for carposinid moths were synthesized and evaluated for biological activity. The analogues aimed to take advantage of the structural commonality of (7Z)-alken-11-ones found in this family. Analogues were tested on two pest species: Heterocrossa rubophaga and Coscinoptycha improbana. Two of the analogues, (2Z)-nonenyl nonanoate and (4Z)-heptyl undecenoate, elicited significant electroantennogram responses. Only (4Z)-heptyl undecenoate gave consistent responses with both moth species in single sensillum recording. Field trapping trials were conducted with these two analogues both individually and in combination with the pheromone of each of the two moth species. No attraction was observed to either of the analogues alone, by either moth species. However, when (4Z)-heptyl undecenoate was coupled with the pheromone, it produced a strong inhibitory effect in H. rubophaga, reducing male moth trap catch by over 95%. No inhibitory effect on male moth trap catch was observed in C. improbana.
Method for synthesizing sex pheromone of carposina niponensis
-
Paragraph 0040-0042, (2019/07/16)
The invention belongs to the technical field of green pesticide synthesis, and discloses a new method for synthesizing sex pheromone of carposina niponensis. According to the method, 3-bromo-1-propanol serves as an initial raw material, alcoholic hydroxyl groups are protected first, and THP protected bromhydrin is obtained; then, the THP protected bromhydrin and 1-octyne are coupled to obtain THPprotected alkynol; hydrogenation reduction is carried out under the catalysis of nickel acetate and sodium borohydride to obtain THP protected Z type enol; then, deprotection and PDC oxidation are carried out to obtain Z type olefine aldehyde; finally, the Z type olefine aldehyde and N-octylmagnesiumromide or N-nonylmagnesiumromide are subjected to an addition reaction and PDC oxidation, and the target product sex pheromone of the carposina niponensis is obtained, namely (Z)-13-eicosylene-10-one and (Z)-12-nonadecene-9-one. According to the method, a triple bond is subjected to hydrogenation reduction under the catalysis of the nickel acetate and the sodium borohydride to construct a Z type double bond, reaction conditions are mild, and the method is environmentally friendly.
Isolation, Synthesis, and Biological Activity of Chlorinated Alkylresorcinols from Dictyostelium Cellular Slime Molds
Kikuchi, Haruhisa,Ito, Ikuko,Takahashi, Katsunori,Ishigaki, Hirotaka,Iizumi, Kyoichi,Kubohara, Yuzuru,Oshima, Yoshiteru
supporting information, p. 2716 - 2722 (2017/11/06)
Eight chlorinated alkylresorcinols, monochasiol A-H (1-8), were isolated from the fruiting bodies of Dictyostelium monochasioides. Compounds 1-8 were synthesized to confirm their structures and to obtain sufficient material for performing biological tests. Monochasiol A (1) selectively inhibited the concanavalin A-induced interleukin-2 production in Jurkat cells, a human T lymphocyte cell line. Monochasiols were biogenetically synthesized by the combination of biosynthetic enzymes relating to the principal polyketides, MPBD and DIF-1, produced by Dictyostelium discoideum.
A novel synthesis of γ,δ-unsaturated aldehydes from α-formyl-γ-lactones
Snowden, Roger L.,Brauchli, Robert,Linder, Simon
experimental part, p. 1216 - 1225 (2011/09/16)
A preparatively useful one-step transformation of γ,γ- disubstituted α-formyl-γ-lactones into trisubstituted γ,δ-unsaturated aldehydes is described, by means of catalytic amounts of either AcOH or AcOEt in the vapor phase over a glass support. A mechanistic rationale is proposed. Copyright
Facile syntheses for (5Z,9Z)-5,9-hexadecadienoic acid, (5Z,9Z)-5,9-nonadecadienoic acid, and (5Z,9Z)-5,9-eicosadienoic acid through a common synthetic route
Carballeira, Nestor M.,Emiliano, Anastacio,Guzman, Aikomari
, p. 33 - 40 (2007/10/03)
The Δ5,9 fatty acids (5Z,9Z)-5,9-hexadecadienoic acid, (5Z,9Z)-5,9-nonadecadienoic acid, and (5Z,9Z)-5,9-eicosadienoic acid were synthesized for the first time in four steps (9-12% overall yield) starting from commercially available 2-(2-bromoethyl)-1,3-dioxolane. The synthetic approach provided enough material to corroborate the structure and stereochemistry of (5Z,9Z)-5,9-nonadecadienoic acid which was recently identified in the flowers of Malvaviscus arboreus (Malvaceae). The novel phospholipids 1-hexadecanoyl-2-[(5Z,9Z)-5,9-eicosadienoyl]-sn-glycero-3-phosphocholine and 1-octadecanoyl-2-[(5Z,9Z)-5,9-eicosadienoyl]-sn-glycero-3-phosphocholine were also synthesized from commercially available L-α-phosphatidylcholine (egg yolk) and characterized by positive ion electrospray mass spectrometry. These are the first examples of unsymmetrical phospholipids with saturated fatty acids at the sn-1 position and Δ5,9 fatty acids at the sn-2 position. Copyright (C) 1999 Elsevier Science Ireland Ltd.
PALLADIUM-CATALYSED REACTION OF VINYLIC HALIDES WITH PRIMARY ALLYLIC ALCOHOLS: REGIO AND STEREOCONTROLLED SYNTHESIS OF 4-ENALS.
Jeffery, Tuyet
, p. 6641 - 6644 (2007/10/02)
Stereodefined γ,δ-unsaturated aldehydes can be prepared with high regio and stereocontrol by palladium-catalysed coupling of vinylic halides with primary allylic alcohols, in the presence of silver carbonate and tetra-n-butylammonium hydrogen sulphate.
OZONOLYSIS OF ALKENES AND REACTIONS OF POLYFUNCTIONAL COMPOUNDS. XLII. SYNTHESIS OF (9Z)-TETRADECENYL ACETATE AND (9Z)-HEXADECENAL FROM (Z,Z)-1,5-CYCLOOCTADIENE
Odinokov, V. N.,Galeeva, R. I.,Ishmuratov, G. Yu.,Kargapol'tseva, T. A.,Sokol'skaya, O. V.,et al.
, p. 1986 - 1989 (2007/10/02)
A stereocontrolled synthesis of (9Z)-tetradecenyl acetate and (9Z)-hexadecenal, which are components of the sex pheromones of the pine (Panolis flammea) and cotton (Heliothis armigera) moths respectively, was realized on the basis of the partial ozonolysis of (Z,Z)-1,5-cyclooctadiene.
Synthesis of (Z)-7-Nonadecen-11-one and (Z)-7-Eicosen-11-one, Sex Pheromone Components of Peach Fruit Moth, Carposina noponensis Walsingham
Vig, O. P.,Sharma, M. L.,Taneja, K. C.,Malik, Neera
, p. 863 - 865 (2007/10/02)
Catalytic hydrogenation of 2-nonyn-1-ol (III) in the presence of Lindlar's catalyst provides (Z)-2-nonen-1-ol (IV) which on bromination followed by alkylation with ethyl monosodiomalonate furnishes the diester (VI).Decarbethoxylation of VI with NaCl/DMSO to monoester (VII), followed by LAH reduction, yields the carbinol (VIII) which on treatment with Corey's reagent gives the aldehyde (IX) in good yield.Aldehyde (IX) on Grignard reaction with 1-bromooctane and 1-bromononane separately provides the alcohols (X) and (XI), respectively.The alcohols (X) and (XI) on oxidation with Corey's reagent yield the title ketones, (Z)-7-nonadecen-11-one (I) and (Z)-eicosen-11-one (II), respectively.
