高等学校化学学报

高等学校化学学报 ›› 2001, Vol. 22 ›› Issue (11): 1829.

• 研究论文 • 上一篇    下一篇

1,5-苯并硫氮杂-β-内酰胺衍生物的不对称合成及晶体结构

李媛1, 张萍1, 李旭2, 张丽君1   

  1. 1. 河北师范大学化学系, 石家庄 050016;
    2. 中国人民武装警察部队学院基础部, 廊坊 065000
  • 收稿日期:2000-08-31 出版日期:2001-11-24 发布日期:2001-11-24
  • 通讯作者: 李媛(1957年出生),女,硕士,教授,从事有机合成研究.
  • 基金资助:

    河北省自然科学基金(批准号:200154)资助

Asymmetric Synthesis and Crystal Structure of β-Lactam Derivatives of1,5-Benzothiazepines

LI Yuan1, ZHANG Ping1, LI Xu2, ZHANG Li-Jun1   

  1. 1. Department of Chemistry, Hebei Normal University, Shijiazhuang 050016, China;
    2. Department of Basic Course, The Chinese Policemen Army College, Langfang 065000, China
  • Received:2000-08-31 Online:2001-11-24 Published:2001-11-24

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摘要： 用(-)-4R-苯基唑烷酮为手性诱导试剂,N-端保护的N-乙酰氯与1,5-苯并硫氮杂反应合成了5个具有光学活性的1,5-苯并硫氮杂-β-内酰胺衍生物,并通过1HNMR,MS,IR,[α]D20和元素分析对此类化合物进行了表征,用X射线衍射法确定了产物Ⅱb的立体结构.晶体X射线衍射分析结果表明,化合物Ⅱb属单斜晶系,P212121空间群,晶胞参数:Mr=553.05,a=1.2293(2)nm,b=2.6026(5)nm,c=1.0146(2)nm,β=90°,V=3.2461nm3,Z=4,Dc=1.312g/cm3,F(000)=1344,R1=0.0584,wR2=0.1140.该化合物分子中七元杂环为类椅式构象,四元环上连接的两个取代基在环的同侧.

关键词: 不对称合成, 1, 5-苯并硫氮杂, &beta, -内酰胺, 4R-苯基唑烷酮

Abstract: Five optially active β-lactam derivatives of1,5 benzothiazepine have been synthesized by the reaction of 1,5 benzothiazepines with Nprotected glycine chloride using chiral oxazolidone as the chiral auxiliary and characterized by elementary analysis, IR,1H NMR, MSand [α]D20. The crystal structure of compound Ⅱb was determined by single crystal X-ray diffraction. Crystal data: Mr=553.05, monoclinic with P212121 space group, a=1.2293(2) nm, b=2.6026(5) nm, c=1.0146(2) nm, β=90°, V=3.2461(10) nm3, F (000)=1344, Z=4, Dc=1.312 g/cm3, R=0.0584, wR=0.1140. The structure analysis reveals that the conformation of sever-membered ring is chair-like, the substituents at C8 and C9 in β-lactam ring are located on the same side.

Key words: Asymmetric synthesis, 1,5-Benzothiazepine, β-Lactam, 4R-Phenyloxazolidone

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