CAS: 495-85-2; (R,E)-6-(2-(Benzo[d][1,3]Dioxol-5-yl)Vinyl)-4-Methoxy-5,6-Dihydro-2H-Pyran-2-One

该化合物是一种自然形成的化合物,被归类为氟甲素,具体地说是一种甲壳素衍生物,主要见于植物物种* Piper methysticum*,通称为kava.该化合物以其...

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CAS号1092383-57-7 4-methoxy-6-vin... | CAS号1682-37-7 3,4-(methylened... | CAS号5876-51-7 1-碘-3,4-亚甲基二氧苯 | CAS号120-57-0 胡椒醛 | CAS号58095-77-5 3,4-methylenedi... | CAS号26536-93-6 methyl 4-bromo-... | CAS号99-50-3 原儿茶酸 | CAS号120-57-0 胡椒醛 | CAS号3155-58-6 7-(1,3-benzodio... | CAS号3155-57-5 二氢卡瓦胡椒素

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    📜1-碘-3,4-亚甲基二氧基苯,(R)-6-((E)-2-(Tributylstannyl)Vinyl)-5,6-Dihydro-4-Methoxypyran-2-One置于tris(Dibenzylideneacetone)Dipalladium (0) 三(2-呋喃基)膦体系中,用 甲苯 作为反应溶剂,以44%的收率获得产物麻醉椒苦素
    参考文献:Versatile Asymmetric Synthesis Of The Kavalactones: First Synthesis Of (+)-Kavain
    标题:Versatile Asymmetric Synthesis Of The Kavalactones: First Synthesis Of (+)-Kavain
    摘要:Three Asymmetric Pathways To The Kavalactones Have Been Developed. The First Method Is Chiral Auxiliary-Based And Utilizes Aldol Reactions Of N-Acetyl Thiazolidinethiones Followed By A Malonate Displacement/decarboxylation Reaction. The Second Approach Uses The Asymmetric Catalytic Mukaiyama Additions Of Dienolate Nucleophile Equivalents Developed By Carreira And Sato. Finally,Tin-Substituted Intermediates,Prepared By Either Of These Routes,Can Serve As Advanced General Precursors Of Kavalactone Derivatives Via Pd(0)-Catalyzed Stille Couplings With Aryl Halides.
    DOI:10.1021/ol0493960

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    专利信息


    专利号:US-11746364-B2
    优先权日:2018-01-17
    标题 :Enzymatic synthesis of kavalactones and flavokavains
    发明人:PLUSKAL TOMÃ?S; Weng jing-ke
    权利人:WHITEHEAD INST BIOMEDICAL RES
    摘要:Disclosed are methods, compositions, proteins, nucleic acids, cells, vectors, compounds, reagents, and systems for the preparation of kavalactones, flavokavains, and kavalactone and flavokavain biosynthetic intermediates using enzymes expressed in heterologous host cells, such as microorganisms or plants, or using in vitro enzymatic reactions. This invention also provides for the expression of the enzymes by recombinant cell lines and vectors. Furthermore, the enzymes can be components of constructs such as fusion proteins. The kavalactones produced can be utilized to treat anxiety disorder, insomnia, and other psychological and neurological disorders. The flavokavains produced can be utilized to treat various cancers including colon, bladder, and breast cancers.

    专利号:US-6677462-B2
    优先权日:2001-08-06
    标题:Asymmetric synthesis of kavalactones
    发明人:CHEN SHOUJUN; SUN LIJUN; MCCLEARY JOEL
    权利人:KAVA PHARMACEUTICALS INC
    摘要:This invention relates to preparation of enantio-enriched compounds, and more particularly to enantio-enriched kavalactone compounds and derivatives thereof. The methods provide compounds that are useful as reagents, or building blocks, in the construction of other enantio-enriched compounds.

    专利号:US-2019271015-A1
    优先权日:2018-01-17
    标题 :Enzymatic synthesis of kavalactones and flavokavains

    专利号:US-10941429-B2
    优先权日:2018-01-17
    标 题:Enzymatic synthesis of kavalactones and flavokavains

    专利号:CA-2456720-A1
    优先权日:2001-08-06
    标题 :Asymmetric synthesis of kavalactones

    专利号:EP-1414463-A4
    优先权日:2001-08-06
    标题 :ASYMMETRIC SYNTHESIS OF KAVALACTONES

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    ✅ COA系统入驻 | 共享模式

    主要参考文献


    1: Li Y, Mei H, Wu Q, Zhang S, Fang JL, Shi L, Guo L. Methysticin and 7,8-dihydromethysticin are two major kavalactones in kava extract to induce CYP1A1. Toxicol Sci. 2011 Dec;124(2):388-99. doi: 10.1093/toxsci/kfr235. Epub 2011 Sep 9. doi: 10.1002/ptr.3283. Epub 2010 Aug 23. doi: 10.1002/bmc.1087. Erratum in: Neuroscience 1998 May;84(1):323. doi: 10.1016/j.bmcl.2009.08.003. Epub 2009 Aug 6.
    8: Abourashed EA, Khan IA. Microbial transformation of kawain and methysticin. Chem Pharm Bull (Tokyo). 2000 Dec;48(12):1996-8. doi: 10.1055/s-0034-1382949. Epub 2014 Aug 6. doi: 10.1016/j.redox.2017.04.024. Epub 2017 Apr 19.
    11: Csupor L. [Quantitative determination of kawa lactones in Piper methysticum (Forster). 2. Determination of kawain, methysticin and yangonin]. Pharmazie. 1970 Mar;25(3):197-8. German. doi: 10.1002/ptr.4656. Epub 2012 Mar 9. German. doi: 10.1002/ptr.3695. Epub 2011 Dec 22. doi: 10.1007/s13197-013-1047-2. Epub 2013 Jun 25.

    合成参考文献


    参考文献:10.1248/bpb.29.834
    摘要:Matsuda H, Hirata N, Kawaguchi Y, Naruto S, Takata T, Oyama M, Iinuma M, Kubo M. Melanogenesis Stimulation in Murine B16 Melanoma Cells by Kava (Piper methysticum) Rhizome Extract and Kavalactones. Biological & Pharmaceutical Bulletin. 2006;29(4):834–7. doi: 10.1248/bpb.29.834.
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