56683-54-6Relevant articles and documents
Stereoselective hydrogenation of 11-hexadecyne-1-ol on supported copper catalysts
Pak,Kartonozhkina,Slepov,Izdebskaya
, p. 1087 - 1090 (1996)
Hydrogenation of 11-hexadecyne-1-ol on 5-30 % copper catalysts supported on γ-Al2O3 and MgCO3 results in as-11-hexadecene-1-ol in 100 % yield. Hydrogenation does not occur on 5-30 % Cu/ZnO catalysts. The difference in behavior of the catalysts is connected with the valent state of copper on the surface and different hydrogen chemisorption.
New fluorinated derivatives as esterase inhibitors. Synthesis, hydration and crossed specificity studies
Quero, Carmen,Rosell, Gloria,Jimenez, Oscar,Rodriguez, Sergio,Bosch, M. Pilar,Guerrero, Angel
, p. 1047 - 1055 (2003)
A variety of new fluorinated chemicals have been prepared for the first time and tested as inhibitors of esterases, one of the main enzymes involved in pheromone catabolism, in two economically important pests, the Egyptian armyworm Spodoptera littoralis (SL) and the Mediterranean corn borer Sesamia nonagrioides (SN). Using the respective major component of the pheromone as substrate, the Km and Vmax of the antennal esterase of both insects resulted to be 5.66×10-4 M and 8.47×10-6 Mmin-1 for SL and 1.61×10-7 M and 1.25×10-7 Mmin-1 for SN, pointing out that SN esterase has a higher affinity for its corresponding substrate than SL. In general, the trifluoromethyl ketones (TFMKs) exhibited higher inhibitory potency than the corresponding difluoromethyl ketones (DFMKs) or difluoroaldehydes (DFAs). The compounds appeared to hydrate differently in aqueous solution, the extent of hydration following the order: α,α-DFMKshyd and the inhibitory potency and no specificity has been found when the chemicals were assayed on extracts of both insects.
Palladium nanoparticlesin situsynthesized onCyclea barbatapectin as a heterogeneous catalyst for Heck coupling in water, the reduction of nitrophenols and alkynes
Le, Van-Dung,Le, T. Cam-Huong,Chau, Van-Trung,Le, T. Ngoc-Duyen,Dang, Chi-Hien,Vo, T. To-Nguyen,Nguyen, Trinh Duy,Nguyen, Thanh-Danh
, p. 4746 - 4755 (2021/03/22)
This study develops an effective method for thein situsynthesis of palladium nanoparticles (PdNPs) usingCyclea barbatapectin as a green reducing and stabilizing reagent. The PdNP@pectin nanocomposite was well characterized by analysis techniques such as UV-vis, FTIR, EDX, XRD, SEM, HR-TEM and STEM-mapping. Crystalline PdNPs were found to be distributed in the size range of 1-25 nm with the highest frequency of 6-12 nm. PdNP@pectin exhibited excellent recyclable catalysis activity for the Heck coupling reaction in water medium. The kinetics and recyclability of nanoparticles were investigated for the catalytic reduction ofo-,m- andp-nitrophenol. The result showed a good catalysis efficiency with five successful recycles without compromising much. In particular, the nanocomposite was used as a catalyst for the conversion of alkynes intocis-alkenes with KOH/DMF as a hydrogenation source. The reaction was also utilized effectively for the synthesis of sex pheromones, includingPlutella xylostella((Z)-11-hexadecen-1-yl acetate) andCylas formicarius((Z)-3-dodecen-1-yl(E)-2-butenoate) with the total yields of 70% and 68%, respectively. Therefore, PdNPs supported onC. barbatapectin are promising catalysis materials for application in various fields.
Method for synthesizing grassland spodoptera litura sex pheromone active ingredients
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Paragraph 0041-0043, (2020/07/02)
The invention belongs to the technical field of green pesticide synthesis, and discloses a novel method for synthesizing grassland spodoptera litura sex pheromone active ingredients (Z)-9-dodecene-1-alcohol acetate, (Z)-9-tetradecene-1-alcohol acetate and (Z)-11-hexadecene-1-alcohol acetate. The method comprises the steps: using bromo-alcohol as a starting raw material; and firstly generating hydroxyl phosphonium salt with triphenylphosphine, then respectively carrying out Wittig coupling reaction with propionaldehyde and valeraldehyde to generate Z-type enol, and finally carrying out acetylation reaction with acetic anhydride to prepare (Z)-9-dodecene-1-alcohol acetate, (Z)-9-tetradecene-1-alcohol acetate and (Z)-11-hexadecene-1-alcohol acetate. According to the method, hydroxyl phosphonium salt is used for Wittig reaction, two steps of hydroxyl protection and deprotection are omitted, the synthetic route is simplified, and the method has the advantages of being environmentally friendly and the like.
Practical Synthesis and Field Application of the Synthetic Sex Pheromone of Rice Stem Borer, Chilo suppressalis (Lepidoptera: Pyralidae)
Chien, Wei-Jynn,Gupta, Sachin,Liu, Bin,Lou, Da Wei,Shen, Yu-Jhe,Syu, Kun-Jie,Tseng, Jui-Chang,Zhang, Yuan-Xin
, (2020/03/11)
Rice stem borer, Chilo suppressalis, is a common and major serious pest of rice, maize, and wheat crops across Asia, Europe, and Oceania countries. Its sex pheromone consists of three analogously compounds, i.e., (Z)-hexadec-11-enal (1), (Z)-octadec-13-enal (2), and (Z)-hexadec-9-enal (3), as long-chain aliphatic internal cis-alkenyl aldehydes. In order to perform an economic and widespread pest control management of rice stem borer, a versatile and efficient synthetic strategy is required. A versatile and efficient synthesis using a common synthetic route for cis-alkenals with high overall yields is described. Commercially available inexpensive aliphatic diols were chosen as starting materials. Two key steps were employed to synthesize the long-chain aliphatic internal cis-alkenes in excellent yields, including the alkylation of terminal alkynes without the utilization of a highly polar aprotic cosolvent and the versatile cis-selective semihydrogenation for the reduction of internal alkynes with excellent stereoselectivity. The results of field tests showed that the synthetic sex pheromone blend was highly effective for the capture of rice stem borer.
A moth pheromone pickles preparation method (by machine translation)
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Paragraph 0024, (2019/05/15)
The invention discloses a method for preparing a moth pheromone pickles, characterized in that comprises the following steps: S1, taking eleven vinyl alcohol synthesis undecene - 11 - ol benzoates; S2, will take Hendecane glycol synthesis Hendecane mono benzoates; S3, synthetic undecanal - 11 - ol benzoates; S4, synthetic cis - 11 - hexadecenoic - 1 - ol benzoates; S5, synthetic cis - 11 - hexadecenoic - 1 - ol; S6, synthetic cis - 11 - sixteen [...]; S7, synthetic cis - 11 - hexadecenoic - 1 - ethoxylate ester; S8, the composition is mixed, moth pheromone shall pickles. The present invention, adopts a double-sodamide as alkali, phosphine ye li? deodorant pentane as raw material with undecanal - 11 - alcohol benzoate reaction occurs, the reaction yield is as high as 89%, and syn-form isomer content of 98% or more, and the synthetic method is simple. (by machine translation)
A moth pheromone synthesis method of pickles (by machine translation)
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Paragraph 0020, (2018/09/12)
The invention belongs to the technical field of chemical synthesis, in particular relates to a moth pheromone of the pickles synthetic method, comprises the following steps: 1) in the organic solvent, 11 - bromo - 1 - [...] with triphenylphosphine reaction to produce bromo Hendecane [...]; 2) under the protection of nitrogen, step 1) obtained in the bromo Hendecane [...] with valeraldehyde, sodium ethoxide in tetrahydrofuran solvent to react to generate cis - 11 - sixteen-carbon vinyl alcohol; 3) in the dichloromethane solution in, step 2) obtained in the cis - 11 - sixteen carbon alcohol with the occurrence chloro-chromic acid pyridine salt to the oxidizing reaction to produce cis - 11 - sixteen [...]; 4) in dichloromethane in, step 2) obtained in the cis - 11 - sixteen carbon alcohol with acetic anhydride, pyridine reaction to produce cis - 11 - sixteen-carbon vinyl alcohol acetate. The invention uses inexpensive and easily obtained 11 - bromo - 1 - [...] as the starting material, the synthesis step is reduced, simplifies the synthesis process, the product yield is high, the reaction conditions are mild and controllable, low requirements on equipment, can be used for industrial production. (by machine translation)
AGRICULTURAL PHEROMONE COMPOSITIONS COMPRISING POSITIONAL ISOMERS
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, (2017/06/12)
The present disclosure provides pheromone compositions. In some aspects, the compositions taught herein comprise a pheromone chemically corresponding to the pheromone naturally produced by a given insect, along with at least one positional isomer of said pheromone. In various aspects, pheromone compositions of the present disclosure are able to modulate the response of the insect based on the ratio of natural pheromone to its positional isomer.
SYNTHESIS OF OLEFINIC ALCOHOLS VIA ENZYMATIC TERMINAL HYDROXYLATION
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Paragraph 0309; 0311, (2016/01/30)
In certain aspects, the present invention provides methods for producing terminally hydroxylated alkenes and alkynes by contacting an unsaturated or saturated hydrocarbon substrate with a hydroxylase enzyme. Exemplary terminal hydroxylases useful for carrying out the methods of the invention exhibit strong selectivity towards one terminal carbon of a hydrocarbon substrate and include, but are not limited to, non-heme diiron alkane monooxygenases, cytochromes P450 (e.g., cytochromes P450 of the CYP52 and CYP153 family), as well as long chain alkane hydroxylases. In some embodiments, the terminally hydroxylated alkene or alkyne is further converted to a terminal alkenal. In certain embodiments, terminally hydroxylated alkenes and alkynes are useful as insect pheromones which modify insect behavior. In other embodiments, terminally hydroxylated alkenes and alkynes are useful intermediates for producing pheromones via acetylation or oxidation of the alcohol moiety.
Concise syntheses of insect pheromones using Z-Selective cross metathesis
Herbert, Myles B.,Marx, Vanessa M.,Pederson, Richard L.,Grubbs, Robert H.
supporting information, p. 310 - 314 (2013/02/23)
Very short synthetic routes to nine cisolefin-containing pheromones containing a variety of functionality, including an unconjugated (E,Z) diene, are reported (see scheme). These lepidopteran pheromones are used extensively for pest control, and were easily prepared using ruthenium-based Z-selective cross metathesis, highlighting the advantages of this method over less efficient ways to form Z olefins.
