(Z)-methyl 2-azido-3-(3,5-difluoro-4-methoxyphenyl)acrylate | 1539318-37-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (Z)-methyl 2-azido-3-(3,5-difluoro-4-methoxyphenyl)acrylate
• CAS: 1539318-37-0
• 化学式: C₁₁H₉F₂N₃O₃
• 分子量: 269.208
• InChiKey: DGJIBMGNHBQKDA-UITAMQMPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  84.29
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (Z)-methyl 2-azido-3-(3,5-difluoro-4-methoxyphenyl)acrylate 在 三苯基膦 作用下， 以 乙醇 、 水 、 甲苯 为溶剂， 反应 26.0h， 生成 (Z)-4-(3,5-difluoro-4-methoxybenzylidene)-1-methyl-2-(trifluoromethyl)-1H-imidazol-5(4H)-one
  参考文献：
  名称：

  Plug-and-Play Fluorophores Extend the Spectral Properties of Spinach

  摘要：

  Spinach and Spinach2 are RNA aptamers that can be used for the genetic encoding of fluorescent RNA. Spinach2 binds and activates the fluorescence of (Z)-4-(3,5-difluoro-4-hydroxybenzylidene)-1,2-dimethyl-1H-imidazol-5 (4H)-one (DFHBI), allowing the dynamic localizations of Spinach2-tagged RNAs to be imaged in live cells. The spectral properties of Spinach2 are limited by DFHBI, which produces fluorescence that is bluish-green and is not optimized for filters commonly used in fluorescence microscopes. Here we characterize the structural features that are required for fluorophore binding to Spinach2 and describe novel fluorophores that bind and are switched to a fluorescent state by Spinach2. These diverse Spinach2 fluorophore complexes exhibit fluorescence that is more compatible with existing microscopy filter sets and allows Spinach2-tagged constructs to be imaged with either GFP or YFP filter cubes. Thus, these "plug-and-play" fluorophores allow the spectral properties of Spinach2 to be altered on the basis of the specific spectral needs of the experiment.

  DOI：

  10.1021/ja410819x
• 作为产物：
  描述：

  2-叠氮基乙酸甲酯 、 3,5-二氟-4-羟基苯甲醛 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以62%的产率得到(Z)-methyl 2-azido-3-(3,5-difluoro-4-methoxyphenyl)acrylate
  参考文献：
  名称：

  Plug-and-Play Fluorophores Extend the Spectral Properties of Spinach

  摘要：

  Spinach and Spinach2 are RNA aptamers that can be used for the genetic encoding of fluorescent RNA. Spinach2 binds and activates the fluorescence of (Z)-4-(3,5-difluoro-4-hydroxybenzylidene)-1,2-dimethyl-1H-imidazol-5 (4H)-one (DFHBI), allowing the dynamic localizations of Spinach2-tagged RNAs to be imaged in live cells. The spectral properties of Spinach2 are limited by DFHBI, which produces fluorescence that is bluish-green and is not optimized for filters commonly used in fluorescence microscopes. Here we characterize the structural features that are required for fluorophore binding to Spinach2 and describe novel fluorophores that bind and are switched to a fluorescent state by Spinach2. These diverse Spinach2 fluorophore complexes exhibit fluorescence that is more compatible with existing microscopy filter sets and allows Spinach2-tagged constructs to be imaged with either GFP or YFP filter cubes. Thus, these "plug-and-play" fluorophores allow the spectral properties of Spinach2 to be altered on the basis of the specific spectral needs of the experiment.

  DOI：

  10.1021/ja410819x