2-(((3,4,5)-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl)oxymethyl)acrylonitrile | 1108192-55-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(((3,4,5)-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl)oxymethyl)acrylonitrile
• 英文别名: 2-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]prop-2-enenitrile
• CAS: 1108192-55-7
• 化学式: C₁₀H₁₅NO₆
• 分子量: 245.232
• InChiKey: DBRWANAQMUPTPJ-HOTMZDKISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  123
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-(((3,4,5)-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl)oxymethyl)acrylonitrile 、 乙酸酐 在 吡啶 作用下， 反应 4.0h， 以91%的产率得到
  参考文献：
  名称：

  In vitro anti-influenza screening of several Euphorbiaceae species: Structure of a bioactive Cyanoglucoside from Codiaeum variegatum

  摘要：

  A bio-guided screening against influenza A virus (FLUAV) was carried out with seven Euphorbiaceae species. The results showed that chromatographic fractions from Phyllantus niruri, Euphorbia pulcherrima and Codiaeum variegatum had relevant anti-FLUAV activity, although only chromatographical subfractions from C. variegatum kept the activity. From this plant, the active compound against FLUAV was isolated. Its structure was assigned as 2-(3,4,5)-trihydroxy-6-hydroxymethyltetrahydropyran-2-yloxymethyl)acrylonitrile (1) on the basis of NMR, mass spectrometry and X-ray diffraction analysis. The compound displayed virucidal activity without impairment of haemagglutination properties of the used virus strain. This is the first report indicating antiviral activity of a cyanoglucoside. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2008.09.003