2-(4-(4'-azidophenylethenyl)-3-cyano-5,5-dimethyl-5H-furan-2-ylidene)malononitrile | 1037718-54-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 2-(4-(4'-azidophenylethenyl)-3-cyano-5,5-dimethyl-5H-furan-2-ylidene)malononitrile
• 英文别名: 2-[4-[2-(4-Azidophenyl)ethenyl]-3-cyano-5,5-dimethylfuran-2-ylidene]propanedinitrile；2-[4-[2-(4-azidophenyl)ethenyl]-3-cyano-5,5-dimethylfuran-2-ylidene]propanedinitrile
• CAS: 1037718-54-9
• 化学式: C₁₈H₁₂N₆O
• 分子量: 328.333
• InChiKey: HPXWFXZKCCRCRC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  95
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-(4-(4'-azidophenylethenyl)-3-cyano-5,5-dimethyl-5H-furan-2-ylidene)malononitrile 生成 (E)-2-(4-(4-aminostyryl)-3-cyano-5,5-dimethylfuran-2(5H)-ylidene)malononitrile
  参考文献：
  名称：

  A Photoactivatable Push−Pull Fluorophore for Single-Molecule Imaging in Live Cells

  摘要：

  We have reengineered a red-emitting dicyanomethylenedihydrofuran push-pull fluorophore so that it is dark until photoactivated with a short burst of low-intensity violet light. Photoactivation of the dark fluorogen leads to conversion of an azide to an amine, which shifts the absorption to long wavelengths. After photoactivation, the fluorophore is bright and photostable enough to be imaged on the single-molecule level in living cells. This proof-of-principle demonstration provides a new class of bright photoactivatable fluorophores, as are needed for super-resolution imaging schemes that require active control of single molecule emission.

  DOI：

  10.1021/ja802883k
• 作为产物：
  描述：

  3-羟基-3-甲基-2-丁酮 在 吡啶 、 magnesium ethylate 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 49.0h， 生成 2-(4-(4'-azidophenylethenyl)-3-cyano-5,5-dimethyl-5H-furan-2-ylidene)malononitrile
  参考文献：
  名称：

  硫化氢红色发射荧光探针及其在活细胞成像中的应用

  摘要：

  硫化氢已成为一种重要的生物信使和重视已经支付给荧光探针设计用于h 2 s到满足H的精确测量要求2 S.在这项工作中，一个新的红色发光荧光探针用于h 2 S是基于叠氮化物与H 2 S还原为胺以及二氰基亚甲基二氢呋喃的荧光团而开发的，因为它的激发和发射波长长。与竞争性阴离子和含硫化物的分析物相比，该探针对H 2 S具有很高的选择性。最后，将探针施加到感测ħ 2 S IN的活细胞。

  DOI：

  10.1016/j.tetlet.2013.03.133

文献信息

• 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。
• A red emission fluorescent probe for hydrogen sulfide and its application in living cells imaging
  作者：Tao Chen、Yi Zheng、Zhaochao Xu、Miao Zhao、Yongnan Xu、Jingnan Cui

  DOI：10.1016/j.tetlet.2013.03.133

  日期：2013.6

  Hydrogen sulfide has emerged as an important biological messenger and much attention has been paid to the design of fluorescent probes for H2S to meet the requirement of accurate measurement of H2S. In this work, a new red emission fluorescent probe for H2S was developed based on the reduction reaction of azide with H2S to amine with the fluorophore of dicyanomethylenedihydrofuran because of its long

  硫化氢已成为一种重要的生物信使和重视已经支付给荧光探针设计用于h 2 s到满足H的精确测量要求2 S.在这项工作中，一个新的红色发光荧光探针用于h 2 S是基于叠氮化物与H 2 S还原为胺以及二氰基亚甲基二氢呋喃的荧光团而开发的，因为它的激发和发射波长长。与竞争性阴离子和含硫化物的分析物相比，该探针对H 2 S具有很高的选择性。最后，将探针施加到感测ħ 2 S IN的活细胞。
• A Photoactivatable Push−Pull Fluorophore for Single-Molecule Imaging in Live Cells
  作者：Samuel J. Lord、Nicholas R. Conley、Hsiao-lu D. Lee、Reichel Samuel、Na Liu、Robert J. Twieg、W. E. Moerner

  DOI：10.1021/ja802883k

  日期：2008.7.1

  We have reengineered a red-emitting dicyanomethylenedihydrofuran push-pull fluorophore so that it is dark until photoactivated with a short burst of low-intensity violet light. Photoactivation of the dark fluorogen leads to conversion of an azide to an amine, which shifts the absorption to long wavelengths. After photoactivation, the fluorophore is bright and photostable enough to be imaged on the single-molecule level in living cells. This proof-of-principle demonstration provides a new class of bright photoactivatable fluorophores, as are needed for super-resolution imaging schemes that require active control of single molecule emission.