CAS: 500-64-1; (R,E)-4-Methoxy-6-Styryl-5,6-Dihydro-2H-Pyran-2-One

该化合物是一种自然产生的化合物,被归类为kavalactone,产自Kava工厂(Piper methysticum)的根部.该化合物以...

结构式图片

上下游产品

(E)-3-phenylpropenal ((E)-1,3-Dimethoxy-buta-1,3-dienyloxy)-trimethyl-silane ethyl γ-bromo-β-methoxy-cis-crotonate 3-phenyl-propenal7,8-dihydrokawain 5-((E)-2-Hydroxy-4-phenyl-but-3-enyl)-1,2-dihydro-pyrazol-3-one 5,6-dehydrokawain 7,8-dihydrokavain

合成工艺路线路线简述

  • 合成目标产物 L-Kawain 主要起始原料 Trans-Cinnamaldehyde And 2-Butenoic Acid, 4-Bromo-3-Methoxy-, Ethyl Ester, (2Z)-
  • (文献来源)合成步骤主要原料 Trans-Cinnamaldehyde 和 2-Butenoic Acid, 4-Bromo-3-Methoxy-, Ethyl Ester, (2Z)-
(E)-(R)-5-Hydroxy-3-Oxo-7-Phenyl-Hept-6-Enoic Acid Methyl Ester置于potassium Carbonate体系中,用 甲醇,丙酮 作为反应溶剂,化学反应 15.17H,反应生成 醉椒素
参考文献:A New Procedure For The Enantioselective Vinylogous Aldol Reaction Of Chan's Diene
标题:A New Procedure For The Enantioselective Vinylogous Aldol Reaction Of Chan's Diene
摘要:Chiral Delta-Hydroxy-Delta-Ketoesters Are Easily Available Through The Enantio Selective Vinylogous Aldol Reaction Of Chan'S Diene Promoted By A Sicl4/chiral Phosphoramide Catalytic System. The Procedure Is Conveniently Exploited For A Very Rapid Approach To (+)-Kavain,A Natural Bio-Active Alpha-Pyrone Compound. (C) 2007 Elsevier Ltd. All Rights Reserved.
DOI:10.1016/j.Tetasy.2006.12.016

海关参考信息

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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主要参考文献

1. Chua, H.C., Christensen, E.T., Hoestgaard-Jensen, K., et al. Kavain, the major constituent of the anxiolytic kava extract, potentiates GABAA receptors: Functional characteristics and molecular mechanism. PLoS One 11(6), e0157700 (2016). 2. Li, X., Liu, Z., Xu, X., et al. Kava components down-regulate expression of AR and AR splice variants and reduce growth in patient-derived prostate cancer xenografts in mice. PLoS One 7(2), e31213 (2012). 3. Tang, X., and Amar, S. Kavain Inhibition of LPS-Induced TNF-α via ERK/LITAF. Toxicol. Res. (Camb). 5(1), 188-196 (2016). 4. Kormann, E.C., de Aguiar Amaral, P., David, M., et al. Kavain analogues as potential analgesic agents. Pharmacol. Rep. 64(6), 1419-1426 (2012).

合成参考文献


参考文献:10.1021/ol8002282
摘要:Lin L, Chen Z, Yang X, Liu X, Feng X. Efficient enantioselective hetero-Diels-Alder reaction of Brassard's diene with aliphatic aldehydes: a one-step synthesis of (R)-(+)-kavain and (S)-(+)-dihydrokavain. Org Lett. 2008 Mar 20;10(6):1311–4. doi: 10.1021/ol8002282.
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