4-[2-(4'-N,N-diphenylaminobiphenyl-4-yl)vinyl]pyrimidine

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 4-[2-(4'-N,N-diphenylaminobiphenyl-4-yl)vinyl]pyrimidine
• 英文别名: N,N-diphenyl-4-[(E)-2-pyrimidin-4-ylethenyl]aniline
• 化学式: C₂₄H₁₉N₃
• 分子量: 349.435
• InChiKey: ODTAHBGRCQLMGK-SDNWHVSQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  29
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-[2-(4'-N,N-diphenylaminobiphenyl-4-yl)vinyl]pyrimidine 、 4-溴三苯胺 在 [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂ 、 potassium acetate 、 potassium carbonate 作用下， 以 N-甲基吡咯烷酮 为溶剂， 反应 3.0h， 以89%的产率得到4,4′-(2-(pyrimidin-4-yl)ethene-1,1-diyl)bis(N,N-diphenylaniline)
  参考文献：
  名称：

  钌（II）催化的烯基1，n-二嗪（n = 2、3和4）的CH（杂）芳基化：范围，机理和在串联加氢中的应用

  摘要：

  提出了一种通用的钌（II）催化方法，该方法利用一系列合成吸引性的二嗪作为导向基团实现烯基CH键的（杂）芳基化。尽管在远离C–H键活化位点的位置存在额外的氮孤对可能最终使催化剂中毒，但反应时间短（3 h），因此适合于选择性的双C–H键芳基化。在某些情况下，观察到E：Z异构体的混合物，这些混合物在第一步剩下的钌催化剂存在下以串联方式进一步氢化，代表了更困难的C（sp 3）-H键官能化的另一种方法。根据机理研究，意外的E：Z产物的形成似乎是通过在还原消除步骤后进行的热C═C键异构化而发生的。

  DOI：

  10.1021/acs.joc.7b03024
• 作为产物：
  描述：

  4-甲基嘧啶 在 四(三苯基膦)钯 、 甲基三辛基氯化铵 、 sodium carbonate 、 sodium hydroxide 作用下， 以 乙醇 、 水 、 甲苯 为溶剂， 反应 17.0h， 生成 4-[2-(4'-N,N-diphenylaminobiphenyl-4-yl)vinyl]pyrimidine
  参考文献：
  名称：

  Synthesis and Photophysical Investigation of a Series of Push–Pull Arylvinyldiazine Chromophores

  摘要：

  A new series of push-pull arylvinyldiazines has been efficiently prepared by aldol condensation between the appropriate methyldiazine and aromatic aldehyde. The optical absorption and emission properties of these chromophores were studied in different solvents and media. These compounds act as polarity sensors with a strong positive emission solvatochromism. This behavior suggests a highly polar emitting state, which is characteristic of compounds that undergo an internal charge transfer upon excitation. These molecules also exhibit halochromic properties and are potential colorimetric and luminescence pH sensors. The second-order nonlinear properties have been investigated for some of the compounds, and large and positive mu beta are obtained, in particular, for pyrimidine derivatives.

  DOI：

  10.1021/jo3004919

文献信息

• Synthesis and Photophysical Investigation of a Series of Push–Pull Arylvinyldiazine Chromophores
  作者：Sylvain Achelle、Alberto Barsella、Christine Baudequin、Bertrand Caro、Françoise Robin-le Guen

  DOI：10.1021/jo3004919

  日期：2012.4.20

  A new series of push-pull arylvinyldiazines has been efficiently prepared by aldol condensation between the appropriate methyldiazine and aromatic aldehyde. The optical absorption and emission properties of these chromophores were studied in different solvents and media. These compounds act as polarity sensors with a strong positive emission solvatochromism. This behavior suggests a highly polar emitting state, which is characteristic of compounds that undergo an internal charge transfer upon excitation. These molecules also exhibit halochromic properties and are potential colorimetric and luminescence pH sensors. The second-order nonlinear properties have been investigated for some of the compounds, and large and positive mu beta are obtained, in particular, for pyrimidine derivatives.
• Ruthenium(II)-Catalyzed C–H (Hetero)Arylation of Alkenylic 1,<i>n</i>-Diazines (<i>n</i> = 2, 3, and 4): Scope, Mechanism, and Application in Tandem Hydrogenations
  作者：Rafael Gramage-Doria、Sylvain Achelle、Christian Bruneau、Françoise Robin-le Guen、Vincent Dorcet、Thierry Roisnel

  DOI：10.1021/acs.joc.7b03024

  日期：2018.2.2

  C–H bond arylation. Mixtures of E:Z isomeric products were observed in some cases, which were further hydrogenated in a tandem manner in the presence of the remaining ruthenium catalyst from the first step, representing an alternative approach to more difficult C(sp3)–H bond functionalization. According to mechanistic studies, the unexpected E:Z product formation seems to occur by thermal C═C bond isomerization

  提出了一种通用的钌（II）催化方法，该方法利用一系列合成吸引性的二嗪作为导向基团实现烯基CH键的（杂）芳基化。尽管在远离C–H键活化位点的位置存在额外的氮孤对可能最终使催化剂中毒，但反应时间短（3 h），因此适合于选择性的双C–H键芳基化。在某些情况下，观察到E：Z异构体的混合物，这些混合物在第一步剩下的钌催化剂存在下以串联方式进一步氢化，代表了更困难的C（sp 3）-H键官能化的另一种方法。根据机理研究，意外的E：Z产物的形成似乎是通过在还原消除步骤后进行的热C═C键异构化而发生的。