methyl 4-((4-formylphenyl)(phenyl)amino)benzoate | 1016164-20-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: methyl 4-((4-formylphenyl)(phenyl)amino)benzoate
• CAS: 1016164-20-7
• 化学式: C₂₁H₁₇NO₃
• 分子量: 331.371
• InChiKey: QBUHRPGKJAGGOM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.76
• 重原子数：
  25.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  46.61
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  methyl 4-((4-formylphenyl)(phenyl)amino)benzoate 、 2-氨基苯硫醇 以 乙醇 为溶剂， 反应 6.0h， 以87%的产率得到
  参考文献：
  名称：

  Small-molecule fluorescent dyes based on benzothiazole derivatives for targeting endoplasmic reticulum and tissue imaging

  摘要：

  Small-molecule fluorescent dyes with excellent biocompatibility and deep tissue permeability are playing an important part in biological development. Herein, a series of D-A typesmall-molecules L1, L2 and L3 containing different terminal groups have been designed and synthesized, of which the structures were confirmed by single crystal X-ray diffraction analysis. Interestingly, it was found that different end groups within the molecules gave an obvious effect on the fluorescent emission properties while unconspicuous influence on the absorption properties. Moreover, these compounds were successfully applied to fluorescent imaging for staining cellular endoplasmic reticulum (ER) and tissue slice from mouse exhibiting negligible cytotoxicity as well as favourable permeability. These compounds may act as probes for ER targeting and alternative bio-imaging reagents. (C) 2020 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2020.151703
• 作为产物：
  描述：

  4-(二苯基氨基)苯甲酸甲酯 、 N,N-二甲基甲酰胺 在 三氯氧磷 、 sodium hydroxide 作用下， 反应 5.0h， 以65%的产率得到methyl 4-((4-formylphenyl)(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