期刊文献+

有机化学中的异头效应 被引量:3

Anomeric Effect in Organic Chemistry
下载PDF
导出
摘要 1955年Edward首次发现吡喃糖C(1)位的电负性强的取代基处于a键上,随后被Lemieux和Chü定义为异头效应.它是有机化学中最重要的立体电子效应之一,通常存在于有Lp-X-A-Y结构单元的分子中,其中X是带有孤对电子的电负性强的元素,A是一般元素,Y也是电负性强的元素,Lp是X的孤对电子,其轨道与A—Y键反平行.异头效应对分子的结构和反应活性有重要影响.综述了各类化合物中存在的异头效应、广义异头效应、反异头效应及在有机化学中的应用. The anomalous axial preference of electronegative substituents at the anomeric center C(1) of the pyranose ring was first noted by Edward in 1955 and was clearly defined as the anomeric effect by Lemieux and Chu, which plays a defining role in molecular conformation and reactivity, and is now recognized as one of the most important stereo-electronic effect in organic chemistry. The anomeric effect is recognized in an Lp-X-A-Y moiety as a preference for an antiperiplanar arrangement of the lone pair (Lp) and the A--Y bond, where X is a heteroatom, A is an element with intermediate electronegativity, and Y is a group with higher electronegativity (such as oxygen, nitrogen, fluorine, etc.). In this paper, the anomeric effect, general- ized anomeric effect, reverse anomeric effect, endo-anomeric effect and exo-anomeric effect are described. The potential application of the anomeric effect is supplied.
出处 《有机化学》 SCIE CAS CSCD 北大核心 2008年第10期1664-1675,共12页 Chinese Journal of Organic Chemistry
基金 国家自然科学基金(No.20472064) 天津市自然科学基金(No.04304311)资助项目.
关键词 异头效应 广义异头效应 反异头效应 氢键 anomeric effect generalized anomeric effect reverse anomeric effect hydrogen bond
  • 相关文献

参考文献2

二级参考文献6

共引文献13

同被引文献15

  • 1王宝珠,徐晓勇,陶玉成,柯少勇,钱旭红,李忠.嘧啶酮类衍生物的合成及杀虫活性[J].农药学学报,2010,12(4):429-434. 被引量:6
  • 2ZHANG J, Garrossian M, Gardner D, et al. Synthesis and Anticancer Activity Studies of Cyclopamine Derivatives [J]. Bioorganic & Medicinal Chemistry Letters, 2008, 18(4): 1359- 1363.
  • 3Park J, Lee H Y, Cho M H, et al. Development of a Cy3-Labeled Glucose Bioprobe and Its Application in Bioimaging and Screening for Antieancer Agents [J]. Angewandte Chemic International Edition, 2007, 119(12): 2064- 2068.
  • 4Edrada R A, Ebel R, Supriyono A, et al. A New Highly Active Calyeulin Derivate from the Marine Sponge [J]. Journal of Natural Products, 2002, 65(8): 1168--1172.
  • 5Florante A Q, Nand K V. Novel Stereospecificity of the L-Arabinose-Binding Protein [J]. Nature, 1984, 310:381 -- 386.
  • 6Edward J T. Stability of Glycosides to Acid Hydrolysis [J]. Chemistry & Industry (London, United Kingdom), 1955, 1102 -- 1104.
  • 7Deslongchamps P, Rowan D D, Pothier N, et al. 1,7-Dioxaspiro [5.5] Undecanes, an Excellent System for the Study of Stereoelectronic Effects (Anomeric and Exo-Anomeric Effects) in Acetals [J]. Can J Chem, 1981, 59.. 1105 -- 1121.
  • 8Parr R G, Yang W. Density-Functional Theory of' Atoms and Molecules [M]. New York.. Oxford University Press, 1989.
  • 9Frisch M J, Trucks G W, Schlegel H B, et al. Gaussian 03 Revision A1 [M]. Pittsburgh PA: Gonzalez, C and People, A Gaussian Inc, 2003.
  • 10魏荣宝,张大为,刘博,刘洋,李文丽,贾辰熙.螺共轭效应及其应用[J].有机化学,2009,29(4):517-527. 被引量:5

引证文献3

二级引证文献8

相关作者

内容加载中请稍等...

相关机构

内容加载中请稍等...

相关主题

内容加载中请稍等...

浏览历史

内容加载中请稍等...
;
使用帮助 返回顶部