高等学校化学学报 ›› 2011, Vol. 32 ›› Issue (2): 300.

• 研究论文 • 上一篇    下一篇

4-氧-3-氮杂-三环[5.3.1.02.5]十一烷-9-甲酸甲酯的合成与晶体结构

梁国娟1,陈安齐2   

  1. 1. 重庆医科大学药学院, 重庆 400016;
    2. 厦门大学化学化工学院, 厦门 361005
  • 收稿日期:2010-03-29 修回日期:2010-08-06 出版日期:2010-02-10 发布日期:2011-02-23
  • 通讯作者: 梁国娟 E-mail:lgjdhr@163.com
  • 基金资助:

    重庆医科大学科研基金(批准号:  0200101105)资助.

Synthesis and Crystal Structure of 4-Oxo-3-aza-tricyclo-[5.3.1.0.2.5]undecane-9-carb-oxylic Acid Methyl Ester

LIANG Guo-Juan1*, CHEN An-Qi2   

  1. 1. College of Pharmacy, Chongqing Medical University, Chongqing 400016, China;
    2. College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, China
  • Received:2010-03-29 Revised:2010-08-06 Online:2010-02-10 Published:2011-02-23
  • Contact: LIANG Guo-Juan E-mail:lgjdhr@163.com
  • Supported by:

    重庆医科大学科研基金(批准号:  0200101105)资助.

摘要: 以2-金刚烷酮为起始原料,通过烯烃与氯磺酰异腈酸酯的【2+2】环加成等5步反应合成了新型双环β-内酰胺类化合物5。所有化合物的结构均经1H-NMR、IR和MS等手段进行了表征。此外,还采用X-射线单晶衍射分析方法进一步测定了化合物5的空间立体结构,证明烯烃3与氯磺酰异腈酸酯的【2+2】环加成具有高度的立体选择性和位置选择性。

关键词: β-内酰胺, 抗生素;氯磺酰异腈酸酯;【2+2】环加成

Abstract: The [2+2] cycloaddition of chlorosulfonyl isocyanate (CSI) with an alkene is a very effective method for the synthesis of β-lactams. The new type bicyclic β-lactam compound was synthesized by five steps starting from 2-adamantanone employing the [2+2] cycloaddition strategy. Their structures were characterized by 1H NMR、IR spectra and MS techniques, and the structure of 5 was further determined by X-ray single crystal diffraction analyses method. The results indicate that the [2+2] cycloaddition of cyclic alkene 3 with chlorosulfonyl isocyanate proceeded with excellent regio- and stereo-selectivity.

Key words: β-lactam, antibiotic;chlorosulfonyl isocyanate;[2+2]cycloaddition

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