高等学校化学学报

高等学校化学学报 ›› 2001, Vol. 22 ›› Issue (S1): 218.

• 研究论文 • 上一篇    下一篇

3-聚苯乙烯磺酰基丙醇的制备及其在固相有机合成中的应用

孙维敏, 黄文强   

  1. 南开大学吸附分离功能高分子材料国家重点实验室, 高分子化学研究所, 天津 300071
  • 收稿日期:2001-06-25 出版日期:2001-12-31 发布日期:2001-12-31
  • 通讯作者: 黄文强(1940年生),男,硕士,教授,博士生导师,从事功能高分子、组合化学,固相有机合成研究.
  • 基金资助:

    国家自然科学基金(批准号:20074017)资助.

Preparation of 3-(PolystyrylsuIfonyl) propanol and It's Application in Solid-Phase Organic Synthesis

SUN Wei-Min, HUANG Wen-Qiang   

  1. The State Key Laboratory of Functional Polymer Material for Adsorption and Separation, Institute of Polymer Chemistry, Nankai University, Tianjin 300071, China
  • Received:2001-06-25 Online:2001-12-31 Published:2001-12-31

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摘要：

本文采用聚苯乙烯亚磺酸钠树脂1与3-氯丙醇在碘化四正丁胺和碘化钾的存在下反应制备了3-聚苯乙烯磺酰基丙醇树脂2.以该树脂为载体固载了Boc保护的L-丙氨酸,再经封羟基、脱保护、中和,与异氰酸苯酯反应制得聚合物支载的脲6.脲树脂6在酸性或强碱条件下解脱得到取代的海因化合物,在弱碱条件下解脱得到取代的脲化合物.

关键词: 固相合成, 3-聚苯乙烯磺酰基丙醇, 海因, 脲

Abstract:

Synthesis of 3-(polystyrylsulfonyl)propanol resin and its application in solid-phase organic synthesis is reported. Polystyrene sodium sulfinate 1 reacted with 3-chloropropanol in the presence of the phase transfer catalyst Bu4NI and cocatalyst KI to give the 3-(polystyrylsulfonyl)propanol resin 2. The use of resin 2 as a solid support in solid-phase synthesis was discussed. Boc-L-Ala was immobilized onto resin 2 to give resin 3. Hie remaining hydroxyl group was blocked by benzoyl chloride. Then the Boc-protecting group was removed with 6 mol/L HCl in dioxane and then neutralized with Et3N to afford resin 5. Resin 5 was reacted with phenyl isocyanate to give polymer-supported urea 6. Resin 6 was treated with 6 mol/L hydrochloric acid or a saturated mixture of sodium methoxide in methanol to give N-phenyl-4-methyl hydantoin, while resin 6 was cleaved with a solution of dioxane/methanol/4 mol/L sodium hydroxide (V:V:V=30:9:l)(containing 0.1 mol/L NaOH) to afford N-(α-methyl) carboxymethyl-N'-phenyl urea.

Key words: Solid-phase organic synthesis, 3-(Polystyrylsulfonyl)propanol, Hydantoin, Urea

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