methyl 4-[N,N-bis(4-(2,2-dicyanovinyl)phenyl)amino]benzoate | 1016163-99-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: methyl 4-[N,N-bis(4-(2,2-dicyanovinyl)phenyl)amino]benzoate
• 英文别名: methyl 4-[4-(2,2-dicyanoethenyl)-N-[4-(2,2-dicyanoethenyl)phenyl]anilino]benzoate
• CAS: 1016163-99-7
• 化学式: C₂₈H₁₇N₅O₂
• 分子量: 455.475
• InChiKey: BWZBKFHNOYZGJL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  35
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  125
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  methyl 4-(N,N-bis(4-formylphenyl)amino)benzoate 、 丙二腈 在 吡啶 、 乙酸铵 、 溶剂黄146 作用下， 以96%的产率得到methyl 4-[N,N-bis(4-(2,2-dicyanovinyl)phenyl)amino]benzoate
  参考文献：
  名称：

  Synthetic Strategies to Derivatizable Triphenylamines Displaying High Two-Photon Absorption

  摘要：

  [Graphics]A versatile synthetic strategy to access a set of highly fluorescent g-conjugated triphenylamines bearing a functional linker at various positions on one phenyl ring is described. These compounds were designed for large two-photon absorption (2PA) and in particular for labeling of biomolecules. The monoderivatized trisformylated or trisiodinated intermediates described herein allow introduction of a large variety of electron-withdrawing groups required for large 2PA as well as a panel of chemical functions suitable for coupling to biomolecules. The monoderivatized three-branched compounds and in particular the benzothiazole JP-3Bz) series show remarkable linear (high extinction coefficients and high quantum yield) and nonlinear (high 2-photon cross sections) optical properties. Interestingly the presence of functional side chains does not disturb the two-photon absorption. Finally, monoderivatized two-branched derivatives also appear to be valuable candidates. Altogether the good optical properties of the new derivatizable pi-conjugated TPA combined with their small size and their compatibility with bioconjugation protocols suggest that they represent a new chemical class of labels potentially applicable for the tracking of biomolecules using two-photon scanning microscopy.

  DOI：

  10.1021/jo702002y

文献信息

• Synthetic Strategies to Derivatizable Triphenylamines Displaying High Two-Photon Absorption
  作者：Rémy Lartia、Clémence Allain、Guillaume Bordeau、Falk Schmidt、Céline Fiorini-Debuisschert、Fabrice Charra、Marie-Paule Teulade-Fichou

  DOI：10.1021/jo702002y

  日期：2008.3.1

  [Graphics]A versatile synthetic strategy to access a set of highly fluorescent g-conjugated triphenylamines bearing a functional linker at various positions on one phenyl ring is described. These compounds were designed for large two-photon absorption (2PA) and in particular for labeling of biomolecules. The monoderivatized trisformylated or trisiodinated intermediates described herein allow introduction of a large variety of electron-withdrawing groups required for large 2PA as well as a panel of chemical functions suitable for coupling to biomolecules. The monoderivatized three-branched compounds and in particular the benzothiazole JP-3Bz) series show remarkable linear (high extinction coefficients and high quantum yield) and nonlinear (high 2-photon cross sections) optical properties. Interestingly the presence of functional side chains does not disturb the two-photon absorption. Finally, monoderivatized two-branched derivatives also appear to be valuable candidates. Altogether the good optical properties of the new derivatizable pi-conjugated TPA combined with their small size and their compatibility with bioconjugation protocols suggest that they represent a new chemical class of labels potentially applicable for the tracking of biomolecules using two-photon scanning microscopy.