专利号:US-3943157-A 优先权日:1971-07-26 标题 :Synthesis of codling moth attractant 发明人:HENRICK CLIVE A; SIDDALL JOHN B 权利人:ZOECON CORP 摘要:Sterospecific synthesis of an attractant for the codling moth by reacting sorbic aldehyde with an organo-metallic reagent to yield a 1-ether of trans-8-trans-10-dodecadiene-1,7-diol which is reduced via a 7-sulfonic acid ester to yield an ether of trans-8-trans-10-dodecadiene-1-ol and hydrolyzed to trans-8-trans-10-dodecadien-1-ol. ##SPC1##
专利号:US-3818049-A 优先权日:1971-07-26 标题:Synthesis of codling moth attractant 发明人:HENRICK C; SIDDALL J 权利人:ZOECON CORP 摘要:Sterospecific synthesis of an attractant for the codling moth by reacting sorbic aldehyde with an organo-metallic reagent to yield an 1-ether of trans-8-trans-10-dodecadiene-1.7-diol which is reduced via a 7-sulfonic acid ester to yield an ether of trans-8trans-10-dodecadiene-1-ol and hydrolyzed to trans-8-trans-10dodecadien-1-ol.
专利号:WO-9847910-A1 优先权日:1997-04-21 标题:Method for solution phase synthesis of oligonucleotides 发明人:PIEKEN WOLFGANG; MCGEE DANNY; SETTLE ALECIA; ZHAI YANSHENG; HUANG JIANPING; HILL KEN; SMITH RANDALL S 权利人:NEXSTAR PHARMACEUTICALS INC; PIEKEN WOLFGANG; MCGEE DANNY; SETTLE ALECIA; ZHAI YANSHENG; HUANG JIANPING; HILL KEN; SMITH RANDALL S 摘要:This invention discloses an improved method for the sequential solution phase synthesis of oligonucleotides. The method lends itself to automation and is ideally suited for large scale manufacture oligonucleotides with high efficiency.
专利号:US-3856866-A 优先权日:1971-08-20 标题 :Synthesis of codling moth attactant 发明人:HENRICK C; SIDDALL J 权利人:ZOECON CORP 摘要:Stereospecific synthesis of an attractant for the codling moth by reacting a lithium salt of sorbic acid with 6-lithium hexan-1ether to yield a trans-8-trans-10-dodecadien-7-one-1-ether which is reduced to yield a trans-8-trans-10-dodecadien-7-ol-1-ether which in turn is reduced via a 7-sulfonic acid ester to yield a trans-8-trans-10-dodecadien-1-ether and hydrolyzed to trans-8trans-10-dodecadien-1-ol.
专利号:WO-2024105421-A1 优先权日:2022-11-17 标题 :SYNTHESIS OF α,β-UNSATURATED CARBONYLS FROM ALKENES VIA SULFONIUM INTERMEDIATES AND THEIR APPLICATION IN THE SYNTHESIS OF CONJUGATED DIENE PHEROMONES, KAIROMONES, AND RELATED COMPOUNDS 发明人:ANGYAL PÉTER; KOTSCHY ANDRÃ?S MIKLÓS; DUDÃ?S Ã?DÃ?M; SOÓS Tibor; VARGA SZILÃ?RD 权利人:TERMESZETTUDOMANYI KUTATOKOEZPONT; EOETVOES LORAND TUDOMANYEGYETEM 摘要:α,β-Unsaturated aldehydes are useful products as such in agrochemistry, but also potential intermediates for the preparation of important insect pheromones and kairomones. Until now, primarily the thermodynamically more stable (E)-α,β-unsaturated aldehydes have been identified as useful intermediates in the production of conjugated diene pheromone compounds, however, their practical and cost-effective synthesis on an industrial scale remains challenging. The problem to be solved by the present invention is to provide a method for selective oxidation of alkenes to α,β-unsaturated carbonyls which can be further transformed into pheromones and kairomones preferably without isolation and significant loss of the existing stereochemical purity.
专利号:US-6215019-B1 优先权日:1998-09-01 标题 :Synthesis of 5-decenyl acetate and other pheromone components 发明人:PEDERSON RICHARD L; GRUBBS ROBERT H 权利人:TILLIECHEM INC 摘要:The present invention relates to syntheses of 5-decenyl acetate, the major component in Peach Twig Borer pheromone, and other pheromone components. The syntheses entails few reaction steps, use commercially available starting materials, and have relatively short process times. A preferred embodiment of the syntheses involves self-metathesizing 1-hexene in the presence of Grubbs' catalyst, [(PCy3)2Cl2]Ru=CHPh. The resulting 5-decene is then reacted with an alcohol or acetate protected hexene under vacuum to yield 5-decenyl acetate. These syntheses produce good yields without the need for expensive or sophisticated equipment.
[参考文献]: A C Bckman, Et Al. Antennal Response Of Codling Moth Males, Cydia Pomonella L. (Lepidoptera: Tortricidae), To The Geometric Isomers Of Codlemone And Codlemone Acetate. J Comp Physiol A. 2000 Jun;186(6):513-9. [参考文献]: D E Fernández, Et Al. Comparison Of Lures Loaded With Codlemone And Pear Ester For Capturing Codling Moths, Cydia Pomonella, In Apple And Pear Orchards Using Mating Disruption. J Insect Sci. 2010:10:139. [参考文献]: J R Kanter, Et Al. Inhibition Of Cyclic Amp Efflux By Insect Pheromones And Fatty Acids. Febs Lett. 1989 Feb 13;244(1):149-53. [参考文献]: Juan Huang, Et Al. Separating The Attractant From The Toxicant Improves Attract-And-Kill Of Codling Moth (Lepidoptera: Tortricidae). J Econ Entomol. 2013 Oct;106(5):2144-50. [参考文献]: Marta Giner, Et Al. Development And Biological Activity Of A New Antagonist Of The Pheromone Of The Codling Moth Cydia Pomonella. J Agric Food Chem. 2009 Sep 23;57(18):8514-9.
合成参考文献
摘要:Schramm, M. P., Science of Synthesis, (2009) 46, 464. 摘要:Grainger, R. S.; Jervis, P. J., Science of Synthesis, (2009) 46, 425. 摘要:Special Publication of the Entomological Society of America., 78-1(49), 1978 参考文献:10.1038/srep41829 摘要:Gonzalez F, Witzgall P, Walker WB. Antennal transcriptomes of three tortricid moths reveal putative conserved chemosensory receptors for social and habitat olfactory cues. Scientific Reports. 2017 Feb 02;7(1):41829. doi: 10.1038/srep41829.