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昆虫性信息素共轭二烯的合成进展 总被引:1,自引:0,他引:1
许多昆虫性信息素具有共轭二烯的结构,它们的双键位置和几何构型是决定其生物活性的重要因素。立体选择性和区域选择性地合成共轭二烯是有机合成中十分有意义的研究课题。文章综述了昆虫性信息素共轭二烯的合成进展。 相似文献
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昆虫信息素缓释技术的研究进展 总被引:1,自引:0,他引:1
昆虫信息素是一类由昆虫个体释放于体外来调节或诱发同种其它个体行为与反应的化学物质。 近年来,应用昆虫信息素防治虫害是当前有机农业绿色防控的新技术之一。 与传统农药防治虫害相比,信息素具有高效、无毒、不产生抗药性以及对天敌无害的特点。 此外,昆虫信息素通常易降解且挥发性高。 因此,基于信息素的缓释技术引起了科研工作者的广泛关注,是涵盖化学、材料与农业的新兴交叉学科。 通过某种特定的方法或技术使昆虫信息素缓慢控制释放,既能有效防治虫害,减少农药使用,提升环境生态水平,同时也能促进区域环境化学品总量与农业成本的降低。 本文详细综述了昆虫信息素缓释技术的最新研究进展并对发展前景进行了展望。 相似文献
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Olga M. Lezina Svetlana N. Subbotina Larisa L. Frolova Svetlana A. Rubtsova Denis V. Sudarikov 《Molecules (Basel, Switzerland)》2021,26(17)
Chiral γ-ketothiols, thioacetates, thiobenzoate, disulfides, sulfones, thiosulfonates, and sulfonic acids were obtained from β-pinene for the first time. New compounds open up prospects for the synthesis of other polyfunctional compounds combining a biologically active pinane fragment with various pharmacophore groups. It was shown that the syntheses of sulfanyl and sulfonyl derivatives based on 2-norpinanone are characterized by high stereoselectivity in comparison with similar reactions of pinocarvone. The conditions for the preparation of diastereomerically pure thioacetyl and thiobenzoyl derivatives based on pinocarvone, as well as for the chemoselective oxidation of γ-ketothiols with chlorine dioxide to the corresponding thiolsulfonates and sulfonic acids, were selected. The effect of the VO(acac)2 catalyst on the increase in the yields of thiosulfonates was shown. A new direction of the transformation of thiosulfonates with the formation of sulfones was revealed. In the case of pinocarvone-based sulfones, the configuration is inversed at the C2 atom. An epimerization scheme is proposed. 相似文献
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Biswanath Das Joydeep Banerjee Nikhil Chowdhury Anjoy Majhi Gurram Mahender 《Helvetica chimica acta》2006,89(5):876-883
A simple and convenient synthesis of five important insect pheromones by means of Baylis–Hillman adducts is described, i.e., of (2E,4S)‐2,4‐dimethylhex‐2‐enoic acid ( 1 ), a mandibular‐gland secretion of the male carpenter ant in the genus Camponotus, of (+)‐(S)‐manicone ( 2 ) and (+)‐(S)‐normanicone ( 3 ), two mandibular‐gland constituents of Manica ants, and of (+)‐dominicalure‐I ( 6 ) and (+)‐dominicalure‐II ( 7 ), two aggregation pheromones of the lesser grain borer Rhyzopertha dominica (F). For the first time, the potential of the Baylis–Hillman chemistry for the stereoselective synthesis of trisubstituted olefins was successfully applied to the synthesis of these pheromone compounds. 相似文献
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G. Yu. Ishmuratov M. P. Yakovleva V. A. Ganieva D. V. Amirkhanov G. A. Tolstikov 《Chemistry of Natural Compounds》2005,41(6):719-721
A synthesis of optically active 4S-methylhexanal, 1-bromo-3S-methylheptane, and 1-bromo-3S-methylundecane, which are key synthons
for several methyl-branched insect pheromones, that is based on chemically selective transformations of 6-tosyloxy- and 6-iodoisopropyl-4R-methylhexanoates
that are available from L-(-)-menthol was proposed.
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Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 592–593, November–December, 2005. 相似文献
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Abstract The combined use of the nonlinear mapping method with correspondence factor analysis allowed to derive interesting structure-chemoreception relationships in Lepidoptera. A chemotaxonomy of insects based on their responses to pheromones was also proposed. 相似文献
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Lukas Kahlert Darlon Bernardi Maurice Hauser Dr. Laura P. Ióca Prof. Roberto G. S. Berlinck Dr. Elizabeth J. Skellam Prof. Russell J. Cox 《Chemistry (Weinheim an der Bergstrasse, Germany)》2021,27(46):11895-11903
The mycotoxin terrein is derived from the C10-precursor 6-hydroxymellein (6-HM) via an oxidative ring contraction. Although the corresponding biosynthetic gene cluster (BGC) has been identified, details of the enzymatic oxidative transformations are lacking. Combining heterologous expression and in vitro studies we show that the flavin-dependent monooxygenase (FMO) TerC catalyzes the initial oxidative decarboxylation of 6-HM. The reactive intermediate is further hydroxylated by the second FMO TerD to yield a highly oxygenated aromatic species, but further reconstitution of the pathway was hampered. A related BGC was identified in the marine-derived Roussoella sp. DLM33 and confirmed by heterologous expression. These studies demonstrate that the biosynthetic pathways of terrein and related (polychlorinated) congeners diverge after oxidative decarboxylation of the lactone precursor that is catalyzed by a conserved FMO and further indicate that early dehydration of the side chain is an essential step. 相似文献
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E. V. Salimova O. S. Kukovinets V. G. Kasradze F. Z. Galin A. V. Kuchin A. A. Koroleva 《Chemistry of Natural Compounds》2003,39(3):303-306
Oxidative transformationsinvolving the hydroxylsand -methylsof polyprenolsisolated from birch greenery (7-9 isoprene units in the chain) were used to produce ,-diols, diesters, aldehydoalcohols, and hydroxyacids. The products are of interest as potential anti-inflammatory, antiulcer, hepatoprotective, and cardio-active preparations. 相似文献
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《Analytical letters》2012,45(11):909-922
Abstract An isotachophoretic histamine assay has been developed to determine the histamine content in hymenoptera stinging insect venoms. The amount of histamine was lowest in bee venom (0.9%) while the histamine content of vespid venom extracts varied between 2.7–5.2%. Histamine, determined quantitatively by isotachophoresis, correlated well with the histamine values achieved with reversed-phase high performance liquid chromatography. 相似文献
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Isabel W. C. E. Arends Roger A. Sheldon Martin Wallau Ulf Schuchardt 《Angewandte Chemie (International ed. in English)》1997,36(11):1144-1163
Zeolites are viewed by some as the “philosopher's stone” of modern chemistry.[1] They are more or less indispensable in oil refining and petrochemicals manufacture where they are widely applied as solid acid catalysts. More recently attention has been focused on their use in the manufacture of fine chemicals. The synthetic utility of zeolites and related molecular sieves (zeotypes) has been considerably extended by the incorporation of redox metals into their frameworks. The resulting redox molecular sieves catalyze a variety of selective oxidations under mild conditions in the liquid phase. Their structural diversity–including variation of the redox metal, incorporation of metal complexes, and the size and polarity of the micropores–provides the possibility of designing tailor-made solid catalysts (“mineral enzymes”) for liquid-phase oxidations with clean oxidants such as O2, H2O2, and RO2H. Hence, they have enormous potential in industrial organic synthesis as environmentally friendly alternatives to traditional oxidations employing inorganic oxidants in stoichiometric amounts. A primary aim of this review is to familiarize organic chemists with the synthetic potential of redox molecular sieves. An outline of their synthesis, structures, and chemical properties, highlighting their unique advantages, is followed by a discussion of general (mechanistic) features that influence the choice of a suitable catalyst for a particular type of oxidation. The main part of the review deals with the oxidation of various substrates of synthetic interest–such as alkanes, alkenes, (alkyl)arenes, alcohols, and amines–and emphasizes the advantages of redox molecular sieves (including selectivity and stability) over their homogeneous counterparts. New directions towards truly biomimetic solid catalysts, for example zeolite-encapsulated chiral metal complexes as heterogeneous catalysts for asymmetric oxidations, are high-lighted. 相似文献
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Complementary Iron(II)‐Catalyzed Oxidative Transformations of Allenes with Different Oxidants 下载免费PDF全文
Venkata R. Sabbasani Hyunjin Lee Prof. Yuanzhi Xia Prof. Daesung Lee 《Angewandte Chemie (International ed. in English)》2016,55(3):1151-1155
Substituent‐ and oxidant‐dependent transformations of allenes are described. Given the profound influence of the substituent on the reactivity of allenes, the subtle differences in allene structures are manifested in the formation of diverse products when reacted with different electrophiles/oxidants. In general, reactions of nonsilylated allenes involve an allylic cation intermediate by forming a C?O bond, at the sp‐hybridized C2, with either DDQ (2,3‐dichloro‐5,6‐dicyano‐p‐benzoquinone) or TBHP (tert‐butyl hydroperoxide), along with FeCl2?4 H2O (10 mol %). In contrast, silylated allenes favor the formation of propargylic cation intermediates by transferring the allenic hydride to the oxidant, thus generating 1,3‐enynes (E1 product) or propargylic THBP ethers (SN1 product). The formation of these different putative cationic intermediates from nonsilylated and silylated allenes is strongly supported by DFT calculations. 相似文献
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利用色谱-质谱联机技术,在红收获蚁P.barbatus和P.maricopa的毒腺体样品中检测到召引信息素甲基吡嗪(MP)、2,5-二吡嗪(DMP)、3-乙基-2,5-二甲基吡嗪(EDMP)、和三甲基吡嗪(TMP)。利用特征离子色谱技术,在P.barbatus样品中还检测到了含6个碳原子侧链烃基的吡嗪X。根据吡嗪X的质谱图推测其结构为3-仲丁基-2,5-二甲基吡嗪(BDMP)。P.barbatus中DMP,TMP和EDMP的平均相对百分比分别为60.71、26.49、12.80;标准偏差分别为6.91、4.92、5.11;P.maricopa中平均相对百分比和标准偏差分别为47.48、20.35、32.17和15.05、4.05、15.44。 相似文献
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Identification and Synthesis of Macrolide Pheromones of the Grain Beetle Oryzaephilus Surinamensis and the Frog Spinomantis Aglavei 下载免费PDF全文
Susann Hötling Dr. Birte Haberlag Prof. Dr. Matthias Tamm Dr. Jana Collatz Patrick Mack Prof. Dr. Johannes L. M. Steidle Prof. Dr. Miguel Vences Prof. Dr. Stefan Schulz 《Chemistry (Weinheim an der Bergstrasse, Germany)》2014,20(11):3183-3191
Macrolide lactones, the so called cucujolides derived from unsaturated fatty acids, are aggregation pheromones of cucujid grain beetles. Thirty years ago, Oehlschlarger et al. showed that (3Z,6Z)‐dodeca‐3,6‐dien‐11‐olide ( 4 ) and the respective 12‐olide ( 7 ) attract the sawtoothed grain beetle Oryzaephilus surinamensis, whereas (5Z,8Z,13R)‐tetradeca‐5,8‐dien‐13‐olide ( 5 ) increases the response synergistically. The frass of this beetle is attractive for its parasitoid Cephalonomia tarsalis, which potentially can be used for pest control. A GC/MS analysis of attractive frass showed the presence of 5 , together with an unknown isomer. Cucujolide V was tentatively identified also in the femoral glands, pheromone‐releasing structures, of the Madagascan mantelline frog Spinomantis aglavei. Therefore, a new route to synthesize doubly unsaturated macrolides allowing the flexible attachment of the side chain was developed. A straightforward method to obtain Z configured macrolides involves ring‐closing alkyne metathesis (RCAM) followed by Lindlar‐catalyzed hydrogenation. This methodology was extended to homoconjugated diene macrolides by using RCAM after introduction of one Z configured double bond in the precursor by Wittig reaction. A tungsten benzylidyne complex was used as the catalyst in the RCAM reaction, which afforded the products in high yield at room temperature. With the synthetic material at hand, the unknown isomer was identified as the new natural product (5Z,8Z,12R)‐tetradeca‐5,8‐dien‐12‐olide, cucujolide X ( 8 ). Furthermore, the route also allowed the synthesis of cucujolide V in good yield. The natural products were identified by the synthesis of enantiomerically pure or enriched material and gas chromatography on chiral phases. The new macrolide (R)‐ 8 proved to be biologically active, attracting female O. surinamensis, but no males. The synthetic material allowed the identification of (R)‐ 5 in both the beetle and the frog. 相似文献