(E,E,E)-5-{N,N-bis{4-[2-(pyridin-4-yl)vinyl]phenyl}amino}-2-[2-(pyridin-4-yl)vinyl]benzoic acid | 1016164-07-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (E,E,E)-5-{N,N-bis{4-[2-(pyridin-4-yl)vinyl]phenyl}amino}-2-[2-(pyridin-4-yl)vinyl]benzoic acid
• 英文别名: 2-[(E)-2-pyridin-4-ylethenyl]-5-[4-[(E)-2-pyridin-4-ylethenyl]-N-[4-[(E)-2-pyridin-4-ylethenyl]phenyl]anilino]benzoic acid
• CAS: 1016164-07-0
• 化学式: C₄₀H₃₀N₄O₂
• 分子量: 598.704
• InChiKey: ZIRZSFISFTYCFQ-BQHNWJHOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  46
• 可旋转键数：
  10
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  79.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (E,E,E)-5-{N,N-bis{4-[2-(pyridin-4-yl)vinyl]phenyl}amino}-2-[2-(pyridin-4-yl)vinyl]benzoic acid 、 2-(2-(2-氨基乙氧基)乙氧基)乙基氨基甲酸叔丁酯 在 N-羟基-7-氮杂苯并三氮唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 以30%的产率得到[2-(2-{2-[5-{bis[4-(2-(pyridin-4-yl)vinyl)phenyl]amino}-2-(2-(pyridin-4-yl)vinyl)benzoylamino]ethoxy}ethoxy)ethyl]carbamic acid tert-butyl ester
  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
• 作为产物：
  描述：

  (E,E,E)-methyl 5-{N,N-bis{4-[2-(pyridin-4-yl)vinyl]phenyl}amino}-2-[2-(pyridin-4-yl)vinyl]benzoate 在 lithium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 72.0h， 以100%的产率得到(E,E,E)-5-{N,N-bis{4-[2-(pyridin-4-yl)vinyl]phenyl}amino}-2-[2-(pyridin-4-yl)vinyl]benzoic acid
  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.