高等学校化学学报

高等学校化学学报 ›› 1999, Vol. 20 ›› Issue (10): 1574.

• 论文 • 上一篇    下一篇

不对称环磷酸肟酯的合成和生物活性研究

马治华, 邵瑞链, 马红敏, 成俊然, 黄润秋   

  1. 南开大学元素有机化学研究所, 天津 300071
  • 收稿日期:1999-02-07 出版日期:1999-10-24 发布日期:1999-10-24
  • 通讯作者: 邵瑞链
  • 作者简介:马治华,男,25岁,北京大学有机化学研究所博士研究生.
  • 基金资助:

    天津市自然科学基金(批准号:983602711);元素有机化学国家重点实验室基金

Synthesis and Bioactivities of Novel 1,3,2-Dioxaphosphorinane 2-one Containing Arylglyoxylonitrile Oxime

MA Zhi-Hua, SHAO Rui-Lian, MA Hong-Min, CHENG Jun-Ran, HUANG Run-Qiu   

  1. Institute of Elemento Organic Chemistry, State Key Laboratory of Elemento Organic Chemistry, Nankai University, Tianjin 300071, China
  • Received:1999-02-07 Online:1999-10-24 Published:1999-10-24

PDF (PC)

被引次数

28

摘要： 通过反式-2-氯-2-氧-4-苯基-5,5-二甲基-1,3,2-二氧磷杂环己烷(Ⅱ)和α-氰基-芳基甲醛肟(Ⅰa-Ⅰf)在相转移催化条件下反应,制得新型的1,3,2-二氧磷杂环磷酸肟酯(Ⅲa_Ⅲf),产物中的非对映异构体经1HNMR、31PNMR和单晶X射线衍射确证.但化合物Ⅱ与芳基甲醛肟反应,得到芳基甲腈和环磷酸,这可能是生成不稳定的环磷酸醛肟酯(Ⅳ)经Beckmann裂解所致.生物活性测试表明,化合物cis-Ⅲd具有很好的抗烟草花叶病毒活性.

关键词: 1, 3, 2-二氧磷杂环己烷, &alpha, -氰基-芳基甲醛肟, 非对映异构体, 植物病毒抑制活性

Abstract: The reaction of trans-2-chloro-2-oxo-4-phenyl-5,5-dimethyl-1,3,2-dioxapho-sphorinane(Ⅱ) with arylglyoxylonitrile oximes in the presence of PTC resulted in diastereomers of novel cyclic phosphate of arylglyoxylonitrile oxime(Ⅲ). The configuration and ratio of cis/trans diastereomers of Ⅲ were confined by 1HNMR, 31PNMR and X-ray diffraction analysis. The reaction of arylaldoxime with trans-Ⅱ yielded an unstable arylaldoxime cyclic phosphate which was decomposed through Beckmann fragmentation to give nitrile and cyclic phosphate acid. The bioassay indicated that compound cis-Ⅲd showed a high antiviral activity against TMV.

Key words: 1,3,2-Dioxaphosphorinane, Arylglyoxylonitrile oximes, Diastereomers, An-tiphytoviral activity

中图分类号: 

TrendMD: