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有机化学
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有机化学 ›› 2010, Vol. 30 ›› Issue (9): 1377-1382. 上一篇    下一篇

研究简报

α-羟基膦酸酯芳甲酸酯的合成、晶体结构和质谱裂解规律研究

方华1，王东冬2，陈伟珠1,3，赵玉芬2,3，方美娟*,2   

  1. (1国家海洋局第三海洋研究所海洋生物资源化学与化工中心 厦门 361005)
    (2厦门大学医学院药学系 厦门 361005)
    (3厦门大学化学化工学院 福建省化学生物学省重点实验室 厦门 361005)
  • 收稿日期:2009-09-09 修回日期:2010-01-20 发布日期:2010-04-20
  • 通讯作者: 方美娟 E-mail:fangmj@xmu.edu.cn
  • 基金资助:

    福建自然科学基金；厦门市海洋与渔业局科技计划项目;国家级.国家自然科学基金

Synthesis, Crystal Structure and Fragmentation Pathway of Arylcar-boxy Ester of α-Hydroxyphosphonate

Fang Hua1 Wang Dongdong2 Chen Weizhu1,3 Zhao Yufen2,3 Fang Mei-juan*,2   

  1. (1 The Third Institute of Oceanography of the State Oceanic Administration, Xiamen 361005)
    (2 Department of Pharmaceutical Science, Medical College, Xiamen Univer-sity, Xiamen 361005)
    (3 Key Laboratory for Chemical Biology of Fujian Province, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005)
  • Received:2009-09-09 Revised:2010-01-20 Published:2010-04-20
  • Contact: meijuan fang E-mail:fangmj@xmu.edu.cn

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α-羟基膦酸酯与各种取代苯甲酸或吡啶甲酸, 通过酰氯或缩合剂的作用, 合成了一系列的O,O-二烷基-α-苯基-α- (取代芳基甲酸酯基)-甲基膦酸酯的衍生物. 它们的合成收率为61%～84%, 这些化合物的结构经过核磁(1H NMR, 13C NMR和31P NMR)、红外、质谱、元素分析或高分辨质谱确证, 同时化合物C1的结构在晶体结构解析上进一步得到证实. 利用多级质谱分析了化合物C2, C5和C8的质谱裂解规律, 解释了重排离子的形成机制.

关键词: 膦酸酯衍生物, 晶体结构, 裂解途径

Some novel arylcarboxy esters of α-hydroxyphosphonate were synthesized via the reaction of α-hydroxyphosphonate with benzoic acid chloride or isonicotinic acid chloride. Their structures were confirmed by elemental analysis, IR, 1H NMR, 13C NMR, 31P NMR and mass spectra. The crystal structure of compound C1 was determined by X-ray diffractometer. The sodiated adduct of the title compounds appeared a novel rearrangement reaction by positive ion electrospray ionization mass spectrometry in conjunction with tandem mass spectrometry. A possible rearrangement mechanism was proposed.

Key words: arylcarboxy ester of α-hydroxyphosphonate, crystal structure, fragmentation pathway