CAS: 492-87-5; Julocrotine

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    (3S)-3-Amino-1-(2-Phenylethyl)Piperidine-2,6-Dione 1175950-31-8
    Phenylmethyl (3S)-[2,6-Dioxo-1-(2-Phenylethyl)-3-Piperidinyl]Carbamate 1304774-09-1

    合成工艺路线路线简述

      📜(S)-N-((S)-2,6-Dioxo-1-Phenethylpiperidin-3-yl)-N-((R)-1-(4-Methoxyphenyl)Ethyl)-2-Methylbutanamide置于三氟乙酸体系中,化学反应 24.17H,以96%的收率获得产物n-[2,6-二氧代-1-(2-苯基乙基)-3-哌啶基]-2-甲基丁烷酰胺
      参考文献:通过多组分反应化学制备戊二酰亚胺生物碱
      标题:通过多组分反应化学制备戊二酰亚胺生物碱
      摘要:介绍了具有高度生物学意义的戊二酰亚胺生物碱的简洁四步合成路线.通过 Ugi 四组分反应访问支架,从而引入两个变化点.接着是水解,温和条件下的环化和胺脱保护.环化中间体的非对映异构体很容易分离,从而得到光学纯的生物碱.通过这条路线,合成了四种天然产物和十种衍生物.研究了合成方法的范围和局限性.
      DOI:10.1002/ejoc.201801276

      海关参考信息

      专利信息


      专利号:WO-2012002913-A1
      优先权日:2010-07-02
      标 题:Process of forming a cyclic imide
      发明人:HONG SOON HYEOK; ZHANG JIAN; MUTHAIAH SENTHILKUMAR; GHOSH SUBHASH CHANDRA
      权利人:UNIV NANYANG TECH; HONG SOON HYEOK; ZHANG JIAN; MUTHAIAH SENTHILKUMAR; GHOSH SUBHASH CHANDRA
      摘要:A process is provided for the synthesis of a cyclic imide. A primary amine and a diol compound are contacted in the presence of a Ruthenium (II) complex. The Ruthenium (II) catalyst includes at least one of an alicyclic ligand, an aromatic ligand, an arylalicyclic ligand, an arylaliphatic ligand and a phosphine ligand.

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      ✅ COA系统入驻 | 共享模式

      主要参考文献


      1: Ndunda B, Langat MK, Wanjohi JM, Midiwo JO, Kerubo LO. Alienusolin, a new 4α-deoxyphorbol ester derivative, and crotonimide C, a new glutarimide alkaloid from the Kenyan Croton alienus. Planta Med. 2013 Dec;79(18):1762-6. doi: 10.1055/s-0033-1351044. Epub 2013 Dec 19. doi: 10.3762/bjoc.7.175. Epub 2011 Nov 7.
      3: Silva LL, Joussef AC. Synthesis of N-[(3S)-2,6-dioxo-1-(2-phenylethyl)-3-piperidinyl]-(2S)-2-methylbutanamide ((-)-julocrotine). J Nat Prod. 2011 Jun 24;74(6):1531-4. doi: 10.1021/np200234e. Epub 2011 May 5. doi: 10.1007/s00436-010-1973-0. Epub 2010 Jul 27.

      合成参考文献


      参考文献:10.1002/qua.21355
      摘要:Moreira RYO, Brasil DSB, Alves CN, Guilhon GMSP, Santos LS, Arruda MSP, Müller AH, Barbosa PS, Abreu AS, Silva EO, Rumjanek VM, Souza J, da Silva ABF, Santos RHDA. Crystal structure and theoretical calculations of Julocrotine, a natural product with antileishmanial activity. Int J of Quantum Chemistry. 2007 Oct 03;108(3):513–20. doi: 10.1002/qua.21355.
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