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化学学报
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化学学报 ›› 2000, Vol. 58 ›› Issue (3): 363-367. 上一篇    下一篇

研究论文

手性4-膦酸二酯基-3-卤-2(5H)-呋喃酮的合成与结构

李学强;黄敏;陈庆华   

  1. 宁夏大学化学系.银川;广东石油化工高等专科学校;北京师范大学化 学系.北京(100875)
  • 发布日期:2000-03-15

Synthesis and structure of the novel chiral 4-dialkyloxyphosphonyl-2 (5H)-furanones

Li Xueqiang;Huang Min;Chen Qinghua   

  1. Ningxia Univ., Dept of Chem.Yinchuan;Beijing Normal Univ., Dept of Chem..Beijing(100875)
  • Published:2000-03-15

PDF

509

被引次数

42

手性呋喃酮1a-1b与亚磷酸三酯2a-2b通过串联的不对称Michael加成/分子内Michalis-Arbazov重排反应,得到了含磷官能团的新手性化合物,5-(S)-(l-孟氧基)-4-膦酸二酯基-3-卤素-2(5H)-呋喃酮4a-4d。该反应具有条件温和,产率高(86%-95%),光学纯度单一(d.e.≥98%)的特点。通过元素分析,IR,UV,^1HNMR,^1^3CNMR,MS,[α]~D^2^0波谱分析数据以及X射线四圆衍射数据确定了它们的化学结构和绝对构型。

关键词: 锍化合物, 苯酚P, 苯并呋喃P, Ｘ射线衍射分析, 晶体结构

In this paper, we report that the tandem asymmetric Michael addition/internal Michalis-Arbazov reaction of 1 with nucleophilic trialkylphosphites afforded optically pure 5-(S)-l-menthyloxy-4- dialkyloxy-phosphonyl-3-halo-2(5H)-furanones 4a-4d in 86%-95% yield with d.e.≥98%. The optically pure compounds 4a-4d were identified on the basis of their analytical data, such as [α]~D^2^0, UV, IR, ^1H NMR, ^1^3C NMR, MS and elemental analysis. The absolute configuration of the novel chiral phosphorous compound 4b was established X-ray crystallography.

Key words: SULFONIUM COMPOUNDS, PHENOL P, BENZOFURAN P, X-RAY DIFFRACTION ANALYSIS, CRYSTAL STRUCTURE

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