CAS: 142-83-6; (E,E)-2,4-Hexadienal

该化合物其结构特征为六碳链,具有两个相交双环和甲醛功能组;该化合物被归类为不饱和甲醛,有助于其在有机合成中的再活性和潜在应用;Hexa-2-4-dienal通常无色可粉色黄色液体,具有独特的气味,经常被称为脂肪或绿色;有机溶剂溶解,但由于其疏水碳链,溶液在水中有限;同源双环带的存在,增强了其再活性,使其成为各种化学化合物合成的有益中间体,包括芳香剂和调味剂;此外,其结构允许潜在的聚合反应;与许多不饱和的藻类一样,它可能给接触健康带来风险,在处理和使用过程中需要采取适当的安全措施.

结构式图片

相似化合物

110-44-1 2396-84-1 17102-64-6

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ECHA物质C&L通报REACH预注册

上下游产品

CAS号17102-64-6 反式-2,4-己二烯-1-醇 | CAS号5870-86-0 4,6,6-triethoxy... | CAS号123-73-9 2-丁烯醛 | CAS号64724-29-4 三丁基(2-乙氧基乙烯基)锡 | CAS号121712-54-7 N-methoxy-N-met... | CAS号111-28-4 2,4-已二烯-1-醇 | CAS号75-07-0 乙醛 | CAS号6044-68-4 丙烯醛二甲缩醛 | CAS号590-13-6 顺-1-溴-1-丙烯 | CAS号106950-03-2 °Cta-4,6-dien-1... | CAS号3319-99-1 2-(2-噻吩)吡啶 | CAS号145546-15-2 2-penta-1,3-die... | CAS号1515-97-5 2,4-Hexadienal,... | CAS号15192-80-0 s2,4,6-°Ctatrie... | CAS号928-97-2 反式-3-己烯-1-醇 | CAS号928-92-7 (E)-4-己烯-1-醇 | CAS号928-96-1 叶醇 | CAS号110-91-8 吗啉

合成工艺路线路线简述

    山梨酸乙酯置于manganese(Iv) Oxide,二异丁基氢化铝体系中,用 正己烷,二氯甲烷 用作溶剂,化学反应 25.5H,反应生成(E,E)-2,4-己二烯醛
    参考文献:仿生β-酮基多烯硫酸酯的逐步经济合成及其在酶促生物合成研究中的用途.
    标题:仿生β-酮基多烯硫酸酯的逐步经济合成及其在酶促生物合成研究中的用途.
    摘要:多烯硫酯中间体的生物合成工艺研究由于难以获得合适的底物替代物而变得复杂.我们提出了一种仿生的β-酮多烯硫酯的逐步经济合成方法,该方法基于ir催化的还原性horner-Wadsworth-Emmons烯烃化反应.示例性地通过简短的途径合成泛酸的新的β-酮三烯和戊烯硫醚以及n-乙酰基半胱胺.这些化合物的有用性在体外测定中得到了证明,该酮还原酶结构域来自mycolactone生物合成的myckrb.
    Doi:10.1021/acs.Orglett.0C01348

    海关参考信息

    专利信息


    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:US-4131623-A
    优先权日:1969-07-08
    标 题:Synthesis of aldehydes and products of such synthesis
    发明人:MEYERS ALBERT I
    权利人:UNIV LOUISIANA STATE
    摘要:The disclosure describes the production of complex aliphatic, unsaturated and cycloalkane aldehydes utilizing heterocyclic ring compounds, such as oxazines, particularly dihydro-1,3-oxazines. The oxazines are treated with an alkali metal-alkane compound, such as butyl lithium in the presence of an organic solvent at subzero temperature to form an anion of the oxazine. This anion is then alkylated in the anhydrous reaction mixture by introduction of a suitable halide, epoxide or ketone while still at a subzero temperature and mixture is permitted to warm up to room temperature, following which the reaction mixture is acidified, as with hydrochloric acid to pH 2 to 3, extracted and then made basic, as with caustic alkali with cooling. n The reaction mixture is then extracted, as with ether, to produce after evaporation the alkylated dihydro-1,3-oxazine. n The alkylated dihydro-1,3-oxazine is then reacted with an alkali metal or sodium borohydride or borodeuteride or borotritide, with cooling to subzero temperatures at about a neutral pH and then transferred into a basic aqueous environment following extraction of the aqueous layer with an organic solvent, such as ether, to give a tetrahydro-1,3-oxazine. This compound may then be converted to the aldehyde desired by steam distillation or by hydrolysis in the presence of a dilute or weak acid, such as hydrochloric or oxalic acid. The aldehydes may then be extracted. n These aldehydes are useful as components or intermediates in flavoring or perfumes, in insect attractants and repellants, and in pharmaceuticals.

    专利号:US-2005004225-A1
    优先权日:2003-04-16
    标题:Oxidoreductase inhibitors and methods of screening and using thereof
    发明人:BALENDIRAN GANESARATNAM K
    摘要:The present invention relates to 1) the design and synthesis of analogs to glutathione conjugates which bind to or interact with aldose reductase (AR) through unique conformations that are distinctly different from the substrates and inhibitors of AR which are members of sugar metabolism; 2) the screening of the analogs to identify those that interact with or inhibit or enhance the activity of AR; and 3) the use of AR ligands, AR inhibitors (AR antagonsits) or AR enhancer (AR agonists) in the detection of AR activity, the modulation of AR activity, and the treatment of conditions in a subject in need of modulating AR activity. Such conditions include but not limited to cardiovascular disease, diabetes, artheriosclerosis, cancer, neoplasm, obesity, cataract, retinopathy, keratopathy, nephropathy, neurosis, thrombosis, faulty union of corneal injury and neuropathy. Examples of the treatment include the use of fibrates as AR inhibitors to treat these conditions.

    专利号:US-2012022282-A1
    优先权日:2009-04-17
    标题 :Process for the preparation of 2,4,6-octatriene-1-oic acid and 2,4,6-octatriene-1-ol
    发明人:GIULIANI GIAMMARIA; BENEDUSI ANNA; MILANESE ABERTO
    权利人:GIULIANI GIAMMARIA; BENEDUSI ANNA; MILANESE ABERTO; GIULIANI SPA
    摘要:The present invention concerns a process for synthesis of 2,4,6-octatriene-1-oic acid and 2,4,6-octatriene-1-ol, which comprises the following stages:n a) reaction between 2,4-trans-hexadienal and triethyl phosphonoacetate to give ethyl 2,4,6-trans-octatrienoate; b) alkaline hydrolysis of ethyl 2,4,6-trans-octatrienoate to give the corresponding alkaline salt; c) acidification of said salt to give 2,4,6-trans-octatrienoic acid, which can be separated or can undergo the following further stages: d) reaction of the 2,4,6-trans-octatrienoic acid with ethyl chloroformiate to give the mixed anhydride formed by 2,4,6-trans-octatrienoic acid and ethyl carbonic acid; e) reduction of said mixed anhydride with sodium borohydride to give 2,4,6-trans-octatrienol; and optionally a purification stage of the end product.

    专利号:US-3681297-A
    优先权日:1970-11-10
    标 题 :Synthesis of polybenzothiazolines and polybenzothiazoles by reacting a dialdehyde with an aromatic bis-mercaptoamine
    发明人:ALELIO GAETANO FRANCIS D
    权利人:GAETANO FRANCIS D ALELIO
    摘要:THIS INVENTION DEALS WITH A NOVEL, RELATIVELY SIMPLE PROCESS OF PREPARING POLYBENZOTHIAZOLINES, ((-NH-CH(-)-S-)>AR<(-NH-CH(-Z(-))-S-))N BY REACTING DIALDEHYDES, Z-(CH=O)2, AND (HS)2-AR(-NH2)2 IN A SOLVENT IN AN INERT ATMOSPHERE AND THEREAFTER OXIDIZING THE POLYBENZOTHIAZOLINES TO POLYBENZOTHIAZOLES, ((-N=C(-)-S-)>AR<(-N=C(-Z(-))-S-))N WHEREIN AR REPRESENTS A TETRAVALENT AROMATIC MOIETY IN WHICH THE NITROGEN AND SULFUR ATOMS IN EACH PAIR ARE DISPOSED ORTHO TO EACH OTHER AND Z REPRESENTS A DIVALENT HYDROCARBON MOIETY AS THE RESIDUE OF THE DIALDEHYDE, Z(CHO)2. NEW TYPES, AS WELL AS THE KNOW TYPES OF POLYBENZOTHIAZOLES HAVE BEEN PREPARED BY THIS PROCESS.
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    主要参考文献

    [参考文献]: A Nyska, Et Al. Glutathione S-Transferase Pi Expression In Forestomach Carcinogenesis Process Induced By Gavage-Administered 2,4-Hexadienal In The F344 Rat. Arch Toxicol. 2001 Dec;75(10):618-24.
    [参考文献]: Amélie Slegers, Et Al. Volatile Compounds From Grape Skin, Juice And Wine From Five Interspecific Hybrid Grape Cultivars Grown In Québec (Canada) For Wine Production. Molecules. 2015 Jun 15;20(6):10980-1016.
    [参考文献]: C Janzowski, Et Al. Alpha,Beta-Unsaturated Carbonyl Compounds: Induction Of Oxidative Dna Damage In Mammalian Cells. Mutagenesis. 2003 Sep;18(5):465-70.
    [参考文献]: Gabriela Nava, Et Al. Characterization Of Taenia Solium Cysticerci Microsomal Glutathione S-Transferase Activity. Parasitol Res. 2007 Oct;101(5):1373-81.
    [参考文献]: Jiancai Zhu, Et Al. Comparison Of Aroma-Active Volatiles In Oolong Tea Infusions Using Gc-Olfactometry, Gc-Fpd, And Gc-Ms. J Agric Food Chem. 2015 Sep 2;63(34):7499-510.

    合成参考文献


    摘要:Takeda, T.; Tsubouchi, A., Science of Synthesis, (2009) 46, 82.
    摘要:Aitken, R. A.; Aitken, K. M., Science of Synthesis, (2010) 47, 1044.
    摘要:Aitken, R. A.; Aitken, K. M., Science of Synthesis, (2010) 47, 1041.
    摘要:Mase, N., Science of Synthesis Knowledge Updates, (2013) 3, 413.
    摘要:Sloane, S. E.; Behlow, K. T.; Mills, M. D.; Clark, J. R., Science of Synthesis Knowledge Updates, (2022) 2, 418.
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