波谱学杂志 ›› 2001, Vol. 18 ›› Issue (4): 299-303.

• 研究论文 • 上一篇    下一篇

应用NMR技术确证5-(R)-(1-孟氧基)-2(5H)-呋喃酮与苯甲醛肟1,3-偶极环加成产物的结构

黄海洪1, 张翔1*, 陈庆华2   

  1. 1.中国医学科学院,中国协和医科大学药物研究所, 北京 100050;2.北京师范大学化学系, 北京 100875
  • 收稿日期:2001-07-20 修回日期:2001-08-24 出版日期:2001-12-05 发布日期:2001-12-05
  • 作者简介:黄海洪(1967-),女,硕士,副研究员.*通讯联系人.

STRUCTURAL CONFIRMATION OF TWO ADDICTIVES OBTAINED FROM THE 1,3-DIPOLAR CYCLOADDITION OF BENZALDOXIME TO 5-(R)-(l-ENTHYLOXY)-2(5H)-FURANONE BY NMR TECHNIQUES

HUANG Hai-hong1, ZHANG Xiang1* , CHEN Qing-hua2
  

  1. 1.Institute of Materia Medica, Chinese Academy of Medical Sciences & Peking Union  Medical College, Beijing 100050;
    2.Department of Chemistry, Beijing Normal University, Beijing 100875
  • Received:2001-07-20 Revised:2001-08-24 Online:2001-12-05 Published:2001-12-05
  • About author:*Correspondence author.

摘要:

5-(R)-(l-孟氧基)-2(5H)-呋喃酮(A)与苯甲醛肟(B)进行1,3-偶极环加成反应时得到两个产物, 我们应用NOE及HMBC技术确证了它们的结构. 由于反应物(A)的绝对构型已经X-射线单晶衍射法确证, 因此通过NMR研究产物呋喃酮环上各手性碳的关系, 最终确立产物的绝对构型.

关键词: 1,3-偶极环加成, 绝对构型, NOE, HMBC, 碳氢信号全归属

Abstract:

Compound (Ⅰ) & (Ⅱ) were obtained by the 1,3-dipolar cycloaddition of benzal do xime to 5-(R)-(l-menthyloxy)-2(5H)-furanone. As usual, the structure of an  unknown  compound can only be determined by X-Ray diffraction analysis or by relating it  with the known-configuration compound via chemical method. As the configuration of the former material had been studied by X-Ray diffraction analysis and the known chiral carbon is unaffected during the reaction, the structures of  these two newly obtained products can be simply established by the relationship s between the new-formed and the known chiral centers via the analysis of NMR data (N OEID and HMBC) and the reaction can be shown to occur regioselectivel y.

Key words: 1,3-Dipolar Cycloaddition, Configuration,  1H NMR, 13C NMR, NOE, HMBC

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