2-{2-[2-(4-aminophenyl)vinyl]-6-methylpyran-4-ylidene}malononitrile | 1193501-31-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-{2-[2-(4-aminophenyl)vinyl]-6-methylpyran-4-ylidene}malononitrile
• 英文别名: [(2-ethenyl-4'-aminophenyl)-6-methylpyran-4-ylidene]-malononitrile；2-[2-[2-(4-Aminophenyl)ethenyl]-6-methylpyran-4-ylidene]propanedinitrile；2-[2-[2-(4-aminophenyl)ethenyl]-6-methylpyran-4-ylidene]propanedinitrile
• CAS: 1193501-31-3
• 化学式: C₁₇H₁₃N₃O
• 分子量: 275.31
• InChiKey: IMTNHQGDJCALRR-UHFFFAOYSA-N

物化性质

• 沸点：
  446.9±45.0 °C(Predicted)
• 密度：
  1.316±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  82.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-{2-[2-(4-aminophenyl)vinyl]-6-methylpyran-4-ylidene}malononitrile 在 盐酸 、 sodium nitrite 、 sodium azide 作用下， 以 水 为溶剂， 反应 0.75h， 以45%的产率得到2-{2-[2-(4-azidophenyl)vinyl]-6-methylpyran-4-ylidene}malononitrile
  参考文献：
  名称：

  Fluorogenic compounds converted to fluorophores by photochemical or chemical means and their use in biological systems

  摘要：

  从可光活化的叠氮-π-受体荧光发色团或从叠氮-π-受体荧光发色团与烯烃或炔烃的热反应中衍生的荧光色团被披露。还披露了从炔烃-π-受体荧光发色团与叠氮的热反应中衍生的荧光色团。这些荧光色团可以很容易地被光激活，并可用于标记生物分子，并在活细胞中以单分子水平进行成像。

  公开号：

  US20100029952A1
• 作为产物：
  描述：

  2-{2-[2-(4-azidophenyl)vinyl]-6-methylpyran-4-ylidene}malononitrile 以 乙醇 为溶剂， 以30%的产率得到2-{2-[2-(4-aminophenyl)vinyl]-6-methylpyran-4-ylidene}malononitrile
  参考文献：
  名称：

  Azido Push−Pull Fluorogens Photoactivate to Produce Bright Fluorescent Labels

  摘要：

  Dark azido push-pull chromophores have the ability to be photoactivated to produce bright fluorescent labels suitable for single-molecule imaging Upon illumination, the aryl azide functionality in the fluorogens participates in a photochemical conversion to an aryl amine thus restoring charge-transfer absorption and fluorescence Previously we reported that one compound DCDHF-V-P-azide was photoactivatable Here we demonstrate that the azide-to amine photoactivation process is generally applicable to a variety of push-pull chromophores, and we characterize the photophysical parameters including photoconversion quantum yield photostability and turn-on ratio Azido push-pull fluorogens provide a new class of photoactivatable single molecule probes for flourescent labeling and super-resolution microscopy Lastly we demonstrate that photoactivated push-pull dyes can insert into bonds of nearby biomolecules, simultaneously forming a covalent bond and becoming fluorescent (fluorogenic photoaffinity labeling)

  DOI：

  10.1021/jp907080r

文献信息

• 一种荧光化合物及其在医药上的用途
  申请人：四川大学

  公开号：CN104178132B

  公开（公告）日：2017-01-25

  本发明涉及通式（I）表示的具有Aβ斑块亲和力的荧光化合物，其中通式中的取代基如说明书所示，以及含有该衍生物的组合物。本发明还涉及其制法和其在显像Aβ斑块的方法中的应用。
• Fluorogenic compounds converted to fluorophores by photochemical or chemical means and their use in biological systems
  申请人：Tweg Robert J.

  公开号：US20100029952A1

  公开（公告）日：2010-02-04

  Fluorophores derived from photoactivatable azide-pi-acceptor fluorogens or from a thermal reaction of an azide-pi-acceptor fluorogen with an alkene or alkyne are disclosed. Fluorophores derived from a thermal reaction of an alkyne-pi-acceptor fluorogen with an azide are also disclosed. The fluorophores can readily be activated by light and can be used to label a biomolecule and imaged on a single-molecule level in living cells.

  从可光活化的叠氮-π-受体荧光发色团或从叠氮-π-受体荧光发色团与烯烃或炔烃的热反应中衍生的荧光色团被披露。还披露了从炔烃-π-受体荧光发色团与叠氮的热反应中衍生的荧光色团。这些荧光色团可以很容易地被光激活，并可用于标记生物分子，并在活细胞中以单分子水平进行成像。
• Azido Push−Pull Fluorogens Photoactivate to Produce Bright Fluorescent Labels
  作者：Samuel J. Lord、Hsiao-lu D. Lee、Reichel Samuel、Ryan Weber、Na Liu、Nicholas R. Conley、Michael A. Thompson、Robert J. Twieg、W. E. Moerner

  DOI：10.1021/jp907080r

  日期：2010.11.18

  Dark azido push-pull chromophores have the ability to be photoactivated to produce bright fluorescent labels suitable for single-molecule imaging Upon illumination, the aryl azide functionality in the fluorogens participates in a photochemical conversion to an aryl amine thus restoring charge-transfer absorption and fluorescence Previously we reported that one compound DCDHF-V-P-azide was photoactivatable Here we demonstrate that the azide-to amine photoactivation process is generally applicable to a variety of push-pull chromophores, and we characterize the photophysical parameters including photoconversion quantum yield photostability and turn-on ratio Azido push-pull fluorogens provide a new class of photoactivatable single molecule probes for flourescent labeling and super-resolution microscopy Lastly we demonstrate that photoactivated push-pull dyes can insert into bonds of nearby biomolecules, simultaneously forming a covalent bond and becoming fluorescent (fluorogenic photoaffinity labeling)