2-formyl-2-(1,3,3-trimethylindolin-2-ylidene)acetonitrile | 106421-82-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 2-formyl-2-(1,3,3-trimethylindolin-2-ylidene)acetonitrile
• 英文别名: Propanenitrile, 2-(1,3-dihydro-1,3,3-trimethyl-2H-indol-2-ylidene)-3-oxo-；3-oxo-2-(1,3,3-trimethylindol-2-ylidene)propanenitrile
• CAS: 106421-82-3
• 化学式: C₁₄H₁₄N₂O
• 分子量: 226.278
• InChiKey: FSNRHUFUPQFMBI-UHFFFAOYSA-N

物化性质

• 沸点：
  346.6±42.0 °C(Predicted)
• 密度：
  1.128±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  44.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-formyl-2-(1,3,3-trimethylindolin-2-ylidene)acetonitrile 、 3-(4-methylquinolin-1-ium-1-yl)propane-1-sulfonate 反应 1.0h， 以46%的产率得到3-(4-(3-cyano-3-(1,3,3-trimethylindolin-2-ylidene)prop-1-en-1-yl)quinolin-1-ium-1-yl)propane-1-sulfonate
  参考文献：
  名称：

  Enhanced Photostability of Genetically Encodable Fluoromodules Based on Fluorogenic Cyanine Dyes and a Promiscuous Protein Partner

  摘要：

  Fluoromodules are discrete complexes of biomolecules and fluorogenic dyes. Binding of the dyes to their cognate biomolecule partners results in enhanced dye fluorescence. We exploited a previously reported promiscuous binding interaction between a single-chain, variable fragment antibody protein and a family of cyanine dyes to create new protein-dye fluoromodules that exhibit enhanced photostability while retaining high affinity protein-dye binding. Modifications to the dye structure included electron-withdrawing groups that provide resistance to photo-oxidative damage. Low nanomolar equilibrium dissociation constants were found for the new dyes. Fluorescence microscopy illustrates how yeast can be surface-labeled with three different colors based on a single protein and appropriately chosen dyes.

  DOI：

  10.1021/ja9016864
• 作为产物：
  描述：

  1,3,3-trimethyl-2-cyanomethyleneindoline 、 N-甲基甲酰苯胺 在 三氯氧磷 作用下， 以 邻二氯苯 为溶剂， 以48%的产率得到2-formyl-2-(1,3,3-trimethylindolin-2-ylidene)acetonitrile
  参考文献：
  名称：

  Enhanced Photostability of Genetically Encodable Fluoromodules Based on Fluorogenic Cyanine Dyes and a Promiscuous Protein Partner

  摘要：

  Fluoromodules are discrete complexes of biomolecules and fluorogenic dyes. Binding of the dyes to their cognate biomolecule partners results in enhanced dye fluorescence. We exploited a previously reported promiscuous binding interaction between a single-chain, variable fragment antibody protein and a family of cyanine dyes to create new protein-dye fluoromodules that exhibit enhanced photostability while retaining high affinity protein-dye binding. Modifications to the dye structure included electron-withdrawing groups that provide resistance to photo-oxidative damage. Low nanomolar equilibrium dissociation constants were found for the new dyes. Fluorescence microscopy illustrates how yeast can be surface-labeled with three different colors based on a single protein and appropriately chosen dyes.

  DOI：

  10.1021/ja9016864

文献信息

• Enhanced Photostability of Genetically Encodable Fluoromodules Based on Fluorogenic Cyanine Dyes and a Promiscuous Protein Partner
  作者：Nathaniel I. Shank、Kimberly J. Zanotti、Frederick Lanni、Peter B. Berget、Bruce A. Armitage

  DOI：10.1021/ja9016864

  日期：2009.9.16

  Fluoromodules are discrete complexes of biomolecules and fluorogenic dyes. Binding of the dyes to their cognate biomolecule partners results in enhanced dye fluorescence. We exploited a previously reported promiscuous binding interaction between a single-chain, variable fragment antibody protein and a family of cyanine dyes to create new protein-dye fluoromodules that exhibit enhanced photostability while retaining high affinity protein-dye binding. Modifications to the dye structure included electron-withdrawing groups that provide resistance to photo-oxidative damage. Low nanomolar equilibrium dissociation constants were found for the new dyes. Fluorescence microscopy illustrates how yeast can be surface-labeled with three different colors based on a single protein and appropriately chosen dyes.