CAS: 51020-86-1; 2-Methoxy-4-((2R,3R)-7-Methoxy-3-Methyl-5-((E)-Prop-1-En-1-yl)-2,3-Dihydrobenzofuran-2-yl)Phenol

该化合物是天然产生的碱性藻类,主要产自精液的植物物种,其特点是复杂的分子结构,包括多个手性中心,有助于其特定的立体化学. (-)-Licarin A ,其显著的生物活动,包括潜在的抗炎和抗癌特性,使它成为药物研究的焦点.其溶性特征一般表明有机溶剂中溶性中度,而其稳定性则可能受到光和温度等环境因素的影响.该化合物与生物系统的相互作用,往往通过其与特定受体或酶结合的能力加以调节,这可能导致各种生理影响.与许多自然产品一样,提取和净化过程对于以适合进一步研究或应用的形式获得(-)-Licarin A至关重要.

结构式图片

上下游产品

2-methoxy-4-propenylphenol (E)-2-methoxy-4-(1-propenyl)phenol cis-isoeugenol methanolDehydro-diisoeugenol-acetat 2-(3,4-dimethoxy-phenyl)-7-methoxy-3-methyl-5-propenyl-2,3-dihydro-benzofuran 5-formylvanillin 3-methoxy-4-hydroxybenzoic acid

合成工艺路线路线简述

    📜反式-3-(4-羟基-3-甲氧基苯基)-2-丙烯-1-醇置于吡啶,双氧水,三乙基硼氢化锂,三乙胺,Horseradish Peroxidase体系中,用 四氢呋喃,甲醇,二氯甲烷 作为反应溶剂,化学反应 21.5H,反应生成 利卡灵a
    参考文献:Stereoselective Synthesis Of 8,9-Licarinediols
    标题:Stereoselective Synthesis Of 8,9-Licarinediols
    摘要:The Total Synthesis Of 8,9-Licarinediols Was Selectively Carried Out From Licarin A,Previously Obtained By Oxidative Coupling Of (E)-Isoeugenol. The Corresponding Enantiomerically Pure (+)-And(-)-Licarin A Ester Derivatives Were Subjected To Sharpless Oxidation To Yield The Asymmetric C-8,C-9 Dihydroxylation Products,Whose Absolute Configurations Were Established By Means Of The Cd And NMR Spectroscopic Analyses Of Their Mosher Ester Derivatives. (C) 2000 Elsevier Science Ltd. All Rights Reserved.
    DOI:10.1016/s0040-4020(00)00873-5

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    📌 第三方产品分析报告

    ✅ COA系统入驻 | 共享模式

    主要参考文献


    1: Matsui T, Ito C, Masubuchi S, Itoigawa M. Licarin A is a candidate compound for the treatment of immediate hypersensitivity via inhibition of rat mast cell line RBL-2H3 cells. J Pharm Pharmacol. 2015 Dec;67(12):1723-32. doi: 10.1111/jphp.12475. Epub 2015 Sep 17. doi: 10.1016/j.exppara.2013.07.007. Epub 2013 Jul 24. doi: 10.1016/j.arcmed.2012.12.006. Epub 2013 Jan 4. doi: 10.1016/j.chroma.2011.07.093. Epub 2011 Aug 6. doi: 10.1055/s-2008-1074545. Epub 2008 Jun 3. doi: 10.1016/j.phytochem.2011.04.007. Epub 2011 May 11.
    8: Cabral MM, Barbosa-Filho JM, Maia GL, Chaves MC, Braga MV, De Souza W, Soares RO. Neolignans from plants in northeastern Brazil (Lauraceae) with activity against Trypanosoma cruzi. Exp Parasitol. 2010 Mar;124(3):319-24. doi: 10.1016/j.exppara.2009.11.007. Epub 2009 Nov 26.
    10: Barros LF, Barison A, Salvador MJ, de Mello-Silva R, Cabral EC, Eberlin MN, Stefanello ME. Constituents of the leaves of Magnolia ovata. J Nat Prod. 2009 Aug;72(8):1529-32. doi: 10.1021/np900203y. doi: 10.1007/s10495-018-1449-8. Erratum in: Apoptosis. 2018 Mar 15;:. Review. doi: 10.1016/j.taap.2017.12.015. Epub 2017 Dec 27.

    合成参考文献


    摘要:Kwiecień, H., Science of Synthesis Knowledge Updates, (2014) 4, 235.
    摘要:Mitsudo, K.; Suga, S., Science of Synthesis, (2020) , 449.
    参考文献:10.1055/s-2008-1074545
    摘要:Li F, Yang XW. Simultaneous determination of diastereomers (+)-licarin A and isolicarin A from Myristica fragrans in rat plasma by HPLC and its application to their pharmacokinetics. Planta Med. 2008 Jun;74(8):880–4. doi: 10.1055/s-2008-1074545.
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