高等学校化学学报 ›› 2000, Vol. 21 ›› Issue (12): 1939.

• 论文 • 上一篇    下一篇

芳香型螺双内酯二胺的合成

曲建强, 王德秋, 韩福社, 丁孟贤, 高连勋   

  1. 中国科学院长春应用化学研究所高分子物理与化学国家重点实验室, 中国科学院、中国石化总公司高分子化学联合开放实验室 长春 130022
  • 收稿日期:2000-01-18 出版日期:2000-12-24 发布日期:2000-12-24
  • 通讯作者: 高连勋(1956年出生),博士,研究员,博士生导师,主要从事手性化合物的合成和聚酰亚胺的合成及应用.
  • 基金资助:

    国家自然科学基金(批准号:29774029)资助

Synthesis of Aromatic Diaminospirodilactone

QU Jian-Qiang, WANG De-Qiu, HAN Fu-She, DING Meng-Xian, GAO Lian-Xun    

  1. State Key Laboratoryof Polymer Physicsand Chemistry, Changchun Instituteof App lied Chemistry, Chinese Academy of Sciences;Polymer Chemistry Laboratory, Chinese Academy of Sciencesand China Petrochemical Corporation, Changchun Instituteof App lied Chemistry, Chinese Academy of Sciences, Changchun 130022, China
  • Received:2000-01-18 Online:2000-12-24 Published:2000-12-24

摘要: 以对硝基甲苯和多聚甲醛为原料,经过两种途径合成了二氨基芳香型螺双内酯--6,6′-二氨基-3,3′-螺双苯酞.发现二(2-甲基-5-硝基苯基)甲烷在酸性体系中经氧化反应可高收率地得到二硝基螺双内酯,还原二硝基螺双内酯时发现,在低极性溶剂中主要生成一种稳定的芳香型羟胺类化合物--6,6′-二羟氨基-3,3′-螺双苯酞,在高极性溶剂中主要生成6,6′-二氨基-3,3′-螺双苯酞.通过1HNMR,13CNMR,IR,MS及元素分析确证了二氨基螺双内酯及其中间产物的结构

关键词: 合成, 芳香性螺双内酯, 内酯化, 芳香性羟胺

Abstract: Anew kind of aromatic diaminospirodilactone, i.e. 6,6′-diamino-3,3′-spirobiphthalide, was synthesized through multistep reactions from p nitrotoulene and paraformaldehyde.It was found that dinitrospirolactone could be synthesized directly in the acid system through oxidation reaction with a high yield.The increase of solvent polarity leads to an increase of reduction yield of dinitrolactone.The resulting intermediates6,6′- dihydroxylamino-3,3′ spirobiphthalide and6-amino-6′-hydroxylanimo-3,3′ spirobiphthalide were steady aromatic hydroxylamine.The structures of6,6′-diamino-3,3′-spirobiphthalide and its intermediates were confirmed by1H NMR, 13C NMR, MS, IRand elemental analyses

Key words: Synthesis, Aromatic spirodilactone, Lactonization, Aromatic hydroxylamine

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