CAS: 53939-28-9; (Z)-Hexadec-11-Enal

该化合物是一种不饱和的藻类,其特点是长碳链和晶体构造中的双链.它由16个碳原子组成,第11和第12碳原子之间有双链.这种化合物一般在室内温度下是无色的,可粉黄黄色液体,有独特的脂肪味,经常与某些自然来源相关.它溶于有机溶剂,但由于水分疏漏性,在水中溶解性有限. (Z)-11-Hexadecenal因其在各种生物过程中的作用而著称,包括它在某些昆虫中作为球质的功能,可以影响交配关系行为.此外,它被用于食品和化妆业的香味和调味剂合成中.该化合物的再活性主要归因于碱性功能组,该组可以参与各种化学反应,包括氧化和凝聚.

结构式图片

相似化合物

61301-56-2 2541-61-9 56683-54-6

欧盟法规

ECHA物质ECHA物质欧盟农药活性物质C&L通报REACH预注册

上下游产品

(Z)-11-hexadecen-1-ol (Z)-2-(10-pentadecenyl)-1,3-dioxolane 1,1-dimethoxyhexadec-11Z-ene (Z)-11-hexadecen-1-yl acetate(3E, 13Z)-3,13-°Ctadecadien-1-yl acetate trans-2,cis-13-°Ctadecadien-1-ol (2E,13Z)-2,13-°Ctadecadien-1-ol (2E,13Z)-°Ctadeca-2,13-dienyl acetate

合成工艺路线路线简述

  • 合成目标产物 Cis-11-Hexadecenal 主要起始原料 (Z)-Hexadec-11-En-1-Ol
  • (文献来源)合成步骤主要原料 (Z)-Hexadec-11-En-1-Ol
十一醛置于氧气,双(三甲基硅烷基)氨基钾,Nicotinamide Adenine Dinucleotide Phosphate,Pyridinium Chlorochromate体系中,用 二氯甲烷,丙酮,甲苯 作为反应溶剂,化学反应 2.83H,反应生成 (Z)-11-十六烯醛
参考文献: Synthesis Of Olefinic Alcohols Via Enzymatic Terminal Hydroxylation[fr] Synthèse D'Alcools Oléfiniques Par L'Intermédiaire De L'Hydroxylation Terminale Enzymatique
标题: Synthesis Of Olefinic Alcohols Via Enzymatic Terminal Hydroxylation[fr] Synthèse D'Alcools Oléfiniques Par L'Intermédiaire De L'Hydroxylation Terminale Enzymatique
摘要:在某些方面,本发明提供了一种通过将不饱和或饱和碳氢基质与羟化酶酶接触来生产末端羟基化烯烃和炔烃的方法.用于执行本发明方法的示例末端羟化酶对碳氢基质的一个末端碳具有很强的选择性,包括但不限于非血红素双铁脂烷单氧酶,细胞色素p450(例如,Cyp52和cyp153家族的细胞色素p450)以及长链烷烃羟化酶.在某些实施例中,末端羟基化的烯烃或炔烃进一步转化为末端烯醛.在某些实施例中,末端羟基化的烯烃和炔烃可用作改变昆虫行为的昆虫信息素.在其他实施例中,末端羟基化的烯烃和炔烃是通过乙酰化或氧化醇基团来生产信息素的有用中间体.

海关参考信息

专利信息


专利号:WO-2025056767-A1
优先权日:2023-09-15
标题 :Process for the preparation of enantiomerically enriched aliphatic amines
发明人:BOU HAMDAN FARHAN; GODINEAU EDOUARD; SMEJKAL TOMAS; DUMEUNIER RAPHAEL; BOUSSEMGHOUNE MOHAMED ABDELOUAHAB; BLUM MATHIAS
权利人:SYNGENTA CROP PROTECTION AG
摘要:The present invention relates to a process for the preparation of enantiomerically enriched cyclobutylamines of formula (I) from α-tertiary cyclobutanones and reacting said enantiomerically enriched cyclobutylamines to enantiomerically enriched cyclobutylamides. Such compounds are useful intermediates in the synthesis of microbiocidal thiazole compounds.

专利号:US-10202620-B2
优先权日:2014-05-16
标 题:Synthesis of olefinic alcohols via enzymatic terminal hydroxylation
发明人:COELHO PEDRO; CHEN MIKE M Y; MEINHOLD PETER; CHO CATHERINE MEE-HIE; BUI VU; HEEL THOMAS
权利人:PROVIVI INC
摘要: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.

专利号:US-12344573-B2
优先权日:2018-07-16
标题:Synthesis of straight-chain lepidopteran pheromones through one- or two-carbon homologation of fatty alkenes
发明人:WAMPLER KEITH M; LEE CHOON WOO; ROZZELL DAVID
权利人:PROVIVI INC
摘要:Methods for the preparation of alkenes including insect pheromones are described. The methods include homologation reactions employing reagents such as 1,3-diesters, epoxides, cyanoacetates, and cyanide salts for elongation of starting materials and intermediates by one or two carbon atoms. The alkenes include insect pheromones useful in a number of agricultural applications.

专利号:US-11155505-B2
优先权日:2017-02-17
标题 :Synthesis of pheromones and related materials via olefin metathesis
发明人:WAMPLER KEITH M; BUI VU; ROZZELL DAVID; COELHO PEDRO; FLORUTI ARTHUR; ONDI LEVENTE; MEHDI HASAN; EROS GABOR
权利人:PROVIVI INC
摘要:Methods for preparation of olefins, including 8- and 11-unsaturated monoenes and polyenes, via transition metathesis-based synthetic routes are described. Metathesis reactions in the methods are catalyzed by transition metal catalysts including tungsten-, molybdenum-, and ruthenium-based catalysts. The olefins include insect pheromones useful in a number of agricultural applications.

专利号:WO-2021074309-A1
优先权日:2019-10-16
标 题:1-(3-quinolyl)-3,4-dihydroisoquinoline derivatives as fungicides for combating specific phytopathogens
发明人:WEISS MATTHIAS; QUARANTA LAURA; BOU HAMDAN FARHAN; MAHAJAN ATUL; WILLIAMS SIMON; KILARU JAGADEESH; SEN INDIRA; BIERI STEPHANE; DIGGELMANN MARTIN
权利人:SYNGENTA CROP PROTECTION AG
摘要:1-(3-quinolyl)-3,4-dihydroisoquinoline derivatives of formula (I) as well as a method of combating, preventing or controlling the phytopathogens Mycosphaerella graminicola (Septoria tritici), Fusarium culmorum, Gibberella zeae (Fusarium graminearum) and Monographella nivalis (Microdochium nivale), which comprises applying to the phytopathogen, to the locus of the phytopathogen, or to a plant susceptible to attack by the phytopathogen, or to propagation material thereof, a fungicidally effective amount of a 1-(3-quinolyl)-3,4-dihydroisoquinoline derivative of formula (I). The present description discloses the synthesis of exemplary compounds, formulation examples, relevant biological data (antifungal activity against Mycosphaerella graminicola (Septoria tritici), Fusarium culmorum, Gibberella zeae (Fusarium graminearum) and Monographella nivalis (Microdochium nivale) when spayed on plants), as well as comparative data against three prior art compounds (e.g. pages 52 to 85; formulation examples; examples A1 to A3; table E; compounds E.01 to E.187; biological examples). Exemplary compounds are e.g.: 5-bromo-1-(8-fluoro-3-quinolyl)spiro[4H-isoquinoline-3,1'- cyclopropane] (example A1) 5-bromo-1-(8-fluoro-3-quinolyl)-3,3-dimethyl-4H-isoquinoline (example A2) 1-(8-fluoro-3-quinolyl)-3,3-dimethyl-4H-isoquinoline-5-carbonitrile (example A3)

专利号:WO-2021074311-A1
优先权日:2019-10-16
标题:1-(3-quinolyl)-1,2,3,4-tetrahydroisoquinoline derivatives as fungicides for combating specific phytopathogens
发明人:WEISS MATTHIAS; QUARANTA LAURA; BOU HAMDAN FARHAN; MAHAJAN ATUL; WILLIAMS SIMON; KILARU JAGADEESH; BIERI STEPHANE; DIGGELMANN MARTIN
权利人:SYNGENTA CROP PROTECTION AG
摘要:1-(3-quinolyl)-1,2,3,4-tetrahydroisoquinoline derivatives of formula (I) as well as a method of combating, preventing or controlling the phytopathogens Mycosphaerella graminicola (Septoria tritici), Fusarium culmorum, Gibberella zeae (Fusarium graminearum) and Monographella nivalis (Microdochium nivale), which comprises applying to the phytopathogen, to the locus of the phytopathogen, or to a plant susceptible to attack by the phytopathogen, or to propagation material thereof, a fungicidally effective amount of a 1-(3-quinolyl)-1,2,3,4-tetrahydroisoquinoline derivatives of formula (I). The present description discloses the synthesis of exemplary compounds, formulation examples, relevant biological data (antifungal activity against Mycosphaerella graminicola, Monographella nivalis, Fusarium culmorum and/or Gibberella zeae when spayed on plants) (e.g. pages 47 to 55; examples A1 and A2; compounds E.01 to E.17; table E). An exemplary compounds is e.g.: 3-(5-bromo-3,3-dimethyl-2,4-dihydro-1 H-isoquinolin-1-yl)-8-fluoro- quinoline (example A1)
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主要参考文献

[参考文献]: Andrew R Gibb, Et Al. (Z)-11-Hexadecenal And (3Z,6Z,9Z)-Tricosatriene: Sex Pheromone Components Of The Red Banded Mango Caterpillar Deanolis Sublimbalis. J Chem Ecol. 2007 Mar;33(3):579-89.
[参考文献]: Charles E Linn Jr, Et Al. Support For (Z)-11-Hexadecanal As A Pheromone Antagonist In Ostrinia Nubilalis: Flight Tunnel And Single Sensillum Studies With A New York Population. J Chem Ecol. 2007 May;33(5):909-21.
[参考文献]: Cheng-Lin Peng, Et Al. Identification And Field Bioassay Of The Sex Pheromone Of Trichophysetis Cretacea (Lepidoptera: Crambidae). J Econ Entomol. 2012 Oct;105(5):1566-72.
[参考文献]: D J Chamberlain, Et Al. Field Evaluation Of A Slow Release Pheromone Formulation To Control The American Bollworm, Helicoverpa Armigera (Lepidoptera: Noctuidae) In Pakistan. Bull Entomol Res. 2000 Jun;90(3):183-90.
[参考文献]: Hiroo Kanno, Et Al. Attractiveness Of A Four-Component Pheromone Blend To Male Navel Orangeworm Moths. J Chem Ecol. 2010 Jun;36(6):584-91.

合成参考文献


参考文献:10.1007/s00359-005-0071-8
摘要:Lee SG, Carlsson MA, Hansson BS, Todd JL, Baker TC. Antennal lobe projection destinations of Helicoverpa zea male olfactory receptor neurons responsive to heliothine sex pheromone components. J Comp Physiol A Neuroethol Sens Neural Behav Physiol. 2006 Apr;192(4):351–63. doi: 10.1007/s00359-005-0071-8.
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