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有机化学
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有机化学 ›› 2010, Vol. 30 ›› Issue (04): 601-605. 上一篇    下一篇

研究简报

(S)-(＋)-N-取代吡咯烷甲醇衍生物的合成及晶体结构

尹安琴，薛思佳*，方治坤，陈龙，胥杨   

  1. (上海师范大学生命与环境科学学院 上海 200234)
  • 收稿日期:2009-06-04 修回日期:2009-09-13 发布日期:2010-04-28
  • 通讯作者: 薛思佳 E-mail:sjxue@sh163.net;sjxue@sohu.com;sjxue@shnu.edu.cn
  • 基金资助:

    国家级.国家自然科学基金

Synthesis and Crystal Structure of (S)-(＋)-N-Substituted Pyrrolidinyl Methanol Derivatives

Yin Anqin Xue Sijia* Fang Zhikun Chen Long Xu Yang   

  1. (College of Life and Environment Science, Shanghai Normal University, Shanghai 200234)
  • Received:2009-06-04 Revised:2009-09-13 Published:2010-04-28

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从L-α-脯氨酸出发, 经过酯化、N-烷基化、与格氏试剂反应合成了6个未见文献报道的(S)-(＋)-N-取代吡咯烷甲醇衍生物3a～3f, 其结构经IR, 1H NMR和元素分析测定确证. 并用X射线单晶衍射法测定了化合物(S)-(＋)-N-(5-氯-2-噻唑)甲基-α,α-二苯基-2-吡咯烷甲醇(3e)的晶体结构. 晶体为单斜晶系, 空间群为P2(1), a＝0.8737(14) nm, b＝0.9098(14) nm, c＝1.2180(17) nm, α＝90.00°, β＝92.55(3)°, γ＝90.00°, V＝0.9671(3) nm3, Z＝2, Dc＝1.3217 g/cm3, F(000)＝404, R＝0.0584, wR＝0.1335.

关键词: N-取代吡咯烷甲醇, 单晶结构, 合成

Six unreported (S)-(＋)-N-substituted pyrrolidinyl methanol deivatives 3a～3f were synthesized with L-α-proline as raw materials via esterification, N-alkylation and Grignard reaction. The structures of all newly synthesized compounds were elucidated and confirmed by elemental analysis, IR and 1H NMR spectra. The crystal structure of (S)-(＋)-1-[N-(5-chloro-2-thiazolmethyl)pyrrolidin-2-yl]-1,1-diphenylmethanol (3e) was determined by X-ray diffraction analysis, which belongs to the monoclinic system, space group P2(1) with a＝0.8737(14) nm, b＝0.9098(14) nm, c＝1.2180(17) nm, α＝90.00°, β＝92.55(3)°, γ＝90.00°, V＝0.9671(3) nm3, Z＝2, Dc＝1.3217 g/cm3, F(000)＝404, R＝0.0584, and wR＝0.1335.

Key words: N-substituted pyrrolidinyl methanol, crystal structure, synthesis