4-[N-allyl-N-(4-formylphenyl)amino]benzaldehyde | 207669-94-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 4-[N-allyl-N-(4-formylphenyl)amino]benzaldehyde
• 英文别名: 4-(4-formyl-N-prop-2-enylanilino)benzaldehyde
• CAS: 207669-94-1
• 化学式: C₁₇H₁₅NO₂
• 分子量: 265.312
• InChiKey: XPXAZPPKTNVUQA-UHFFFAOYSA-N

物化性质

• 沸点：
  456.0±40.0 °C(Predicted)
• 密度：
  1.176±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-[N-allyl-N-(4-formylphenyl)amino]benzaldehyde 在 palladium on activated charcoal 甲烷磺酸 作用下， 以 乙醇 为溶剂， 以25%的产率得到4-[N-(4-甲酰基苯基)氨基]苯甲醛
  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：

  在 盐酸 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 2.0h， 以1.9 g的产率得到4-[N-allyl-N-(4-formylphenyl)amino]benzaldehyde
  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

• Photophysical and electrochemical investigation of highly conjugated pyridine based diphenylamine materials
  作者：K. Mahesh、V. Priyanka、A.S. Vijai Anand、S. Karpagam

  DOI：10.1016/j.molstruc.2017.10.058

  日期：2018.2

  Abstract Three simple and small donor-acceptor type conjugated moieties, namely (2Z, 2′Z)-3,3'-((hexylazanediyl)bis (4,1-phenylene))bis (2-(pyridin-2-yl)acrylonitrile) ( DPA-PA-1) , (2Z, 2′Z)-3,3'-((dodecylazanediyl)bis (4,1-phenylene))bis (2-(pyridin-2-yl)acrylonitrile) ( DPA-PA-2) , (2Z,2′Z)-3,3'-((allylazanediyl)bis (4,1-phenylene))bis (2-(pyridin-2-yl)acrylonitrile) DPA-PA-3 have been synthesized

  摘要 三个简单且小的供体-受体型共轭部分，即 (2Z, 2'Z)-3,3'-((hexylazanediyl)bis (4,1-phenylene))bis (2-(pyridin-2-yl)丙烯腈) ( DPA-PA-1) , (2Z, 2'Z)-3,3'-((dodecylazanediyl)bis (4,1-phenylene))bis (2-(pyridin-2-yl)丙烯腈) ( DPA-PA-2)、(2Z,2'Z)-3,3'-((烯丙基氮杂二基)双(4,1-亚苯基))双(2-(吡啶-2-基)丙烯腈)DPA-PA- 3 已根据 Knoevenagel 缩合合成。此处烷基（己基、十二烷基、烯丙基）二苯胺 (DPA) 部分充当电子供体，吡啶-乙腈 (PA) 部分充当电子受体。这些部分最近对光电应用表现出极大的兴趣。DPA-PA-1-3的结构由FT-IR、 1 H NMR和13 C N
• 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.