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有机化学
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有机化学 ›› 2009, Vol. 29 ›› Issue (06): 891-897. 上一篇    下一篇

研究论文

N′-叔丁基-N′-取代苯甲酰基-N-(苯并二氢吡喃-5-甲酰基)肼的 设计合成及晶体结构

黄治强 ; 宋红健; 崔志鹏; 周志强 ; 汪清民*   

  1. (南开大学元素有机化学研究所元素有机化学国家重点实验室 天津 300071)
  • 收稿日期:2008-06-25 修回日期:2008-12-10 发布日期:2009-06-20
  • 通讯作者: 汪清民

Design, Synthesis and Crystal Structure of Novel N′-tert-Butyl-N′- (sub stituted benzoyl)-N-(chromane-5-carbonyl)hydrazine Derivatives

Huang, Zhiqiang; Song, Hongjian ; Cui, Zhipeng; Zhou, Zhiqiang ; Wang, Qingmin*   

  1. (State Key Laboratory of Elemento-organic Chemistry, Institute of Elemento-organic Chemistry,
    Nankai University, Tianjin 300071)
  • Received:2008-06-25 Revised:2008-12-10 Published:2009-06-20
  • Contact: Wang, Qingmin

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被引次数

1

以间羟基苯甲酸为起始原料通过7步反应合成了15个新颖的N′-叔丁基-N′-取代苯甲酰基-N-(苯并二氢吡喃-5-甲酰基)肼类化合物. 中间体3-炔丙氧基苯甲酸甲酯在N,N-二乙基苯胺中发生克莱森重排后得到主要产物苯并吡喃-5-甲酸甲酯和副产物苯并吡喃-7-甲酸甲酯. 通过氢谱、元素分析或高分辨质谱确定了这些化合物的结构, 化合物1a的X射线单晶衍射分析发现苯并二氢吡喃的吡喃环与苯环不共平面, 其中的C(1)和C(2)分别位于相应苯环平面的两侧.

关键词: 双酰肼, 昆虫生长调节剂, 晶体结构, 苯并二氢吡喃

Fifteen new N′-tert-butyl-N′-(substituted benzoyl)-N-(chromane-5-carbonyl)hydrazine derivatives were synthesized from 3-hydroxybenzoic acid. The intermediate methyl 3-(prop-2-ynyloxy)benzoate was refluxed in N,N-diethylaniline to give methyl 2H-chromene-5-carboxylate as main product and methyl 2H-chromene-7-carboxylate as byproduct. The structures of the target compounds were confirmed by 1H NMR spectra, elemental analysis or high resolution mass spectra (HRMS). X-ray diffraction analysis of the target compound 1a shows that the pyran and the benzene rings of the chroman are not coplanar, and the C(1) and C(2) are at both sides of the plane of the corresponding benzene ring.

Key words: N,N′-diacylhydrazine, insect growth regulator, crystal structure, chromane