1,3-bis[p-(dimethylamino)phenyl]-1,3-propanedione | 122065-71-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 1,3-bis[p-(dimethylamino)phenyl]-1,3-propanedione
• 英文别名: 1,3-bis(4-(dimethylamino)phenyl)propane-1,3-dione；1,3-bis[4-(dimethylamino)phenyl]-1,3-propanedione；1,3-Bis[4-(dimethylamino)phenyl]propane-1,3-dione
• CAS: 122065-71-8
• 化学式: C₁₉H₂₂N₂O₂
• 分子量: 310.396
• InChiKey: IIPQUIUZRRELBR-UHFFFAOYSA-N

物化性质

• 沸点：
  496.5±40.0 °C(Predicted)
• 密度：
  1.137±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  40.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Cytochrome鎐frompigeonbreastmuscle 、 1,3-bis[p-(dimethylamino)phenyl]-1,3-propanedione 在 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 8.0h， 以25%的产率得到1-ethyl-4,6-bis(4-(dimethylamino)phenyl)-2(1H)-pyrimidone
  参考文献：
  名称：

  Highly Chromic, Proton-Responsive Phenyl Pyrimidones

  摘要：

  Aryl pyrimidones are pharmacologically relevant compounds whose optical properties have only been partially explored. We report the synthesis and optical characterization of a series of aryl- and diaryl-2(1H)-pyrimidones. The electronic transitions of these chromophores are modulated by the extent of conjugation between the pendant phenyl ring and the pyrimidone core as well as the presence of electron-donating auxochromes. Monoprotonation of the pyrimidone ring results in large hyperchromic and bathochromic shifts as well as switching of fluorescence making these phenyl pyrimidones of interest as sensory materials.

  DOI：

  10.1021/ol2014945
• 作为产物：
  描述：

  4-二甲氨基苯甲酸甲酯 、 4-二甲氨基苯甲酸乙酯 在 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 8.17h， 生成 1,3-bis[p-(dimethylamino)phenyl]-1,3-propanedione
  参考文献：
  名称：

  A simple approach to aggregation-induced emission in difluoroboron dibenzoylmethane derivatives

  摘要：

  The first example of an AIE active BF(2)dbm derivative with a single dimethylamino group connecting to the phenyl ring was revealed. It also showed capability of sensing HCI gas both in solution and in the solid state. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.05.099

文献信息

• Metal‐Free 1,3‐Boronate Rearrangement to Ketones Driven by Visible Light
  作者：Kejia Hao、Defang Li、Dongmin Fu、Peng Zou、Shasha Xie、Yu Lan、Yiyun Chen

  DOI：10.1002/anie.202316481

  日期：2024.1.22

  The first 1,3-boronate rearrangement to ketones is reported. The reaction is driven by visible light irradiation, leading to various β-keto tertiary alcohols under metal-free conditions. The excited state overcomes the energy barrier for the rearrangement, and mechanistic studies have excluded a free-radical reaction pathway.

  报道了第一个 1,3-硼酸酯重排为酮的情况。该反应由可见光照射驱动，在无金属条件下生成各种β-酮叔醇。激发态克服了重排的能垒，并且机理研究已经排除了自由基反应途径。
• Visible‐Light Excitation of Infrared Lanthanide Luminescence via Intra‐Ligand Charge‐Transfer State in 1,3‐Diketonates Containing Push‐Pull Chromophores
  作者：Nail M. Shavaleev、Rosario Scopelliti、Frédéric Gumy、Jean‐Claude G. Bünzli

  DOI：10.1002/ejic.200701197

  日期：2008.3

  AbstractA new 1,3‐diketonato ligand containing both an electron‐donor [4‐(dimethylamino)benzene] and an electron‐acceptor (4‐nitrobenzene) group and its lanthanide complexes have been prepared. They display an intense intra‐ligand charge‐transfer absorption transition in the visible region of the spectrum at 400–550 nm which was utilized to achieve visible‐light excitation of metal‐centred infrared luminescence of NdIII, ErIII and YbIII ions. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)