2-([1,1'-biphenyl]-4-yl)phthalazin-1(2H)-one | 1394916-71-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-([1,1'-biphenyl]-4-yl)phthalazin-1(2H)-one
• 英文别名: 2-(4-Phenylphenyl)phthalazin-1-one；2-(4-phenylphenyl)phthalazin-1-one
• CAS: 1394916-71-2
• 化学式: C₂₀H₁₄N₂O
• 分子量: 298.344
• InChiKey: YIECKMLUVVZTTC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  32.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  碳酸亚乙烯酯 、 2-([1,1'-biphenyl]-4-yl)phthalazin-1(2H)-one 在 silver hexafluoroantimonate 、 [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂ 、 1-金刚烷甲酸 、 三甲基乙酸 作用下， 以40 %的产率得到2-(4-(1-oxophthalazin-2(1H)-yl)-[1,1'-biphenyl]-3-yl)acetaldehyde
  参考文献：
  名称：

  碳酸亚乙烯酯作为潜在甲酰甲基替代物：钌 (II) 催化获取芳基乙醛、芳基乙酸酯和乙缩醛的便利性

  摘要：

  在此，我们报道了一种Ru(II)催化添加剂控制的二氮杂萘酮的直接甲酰甲基化和顺序脱氢酯化，以使用碳酸亚乙烯酯作为C2合成子来获得芳基乙醛、芳基乙酸酯和缩醛。使用各种对照实验并通过质谱法确认可能的中间体来阐明反应机理。

  DOI：

  10.1002/ejoc.202300847
• 作为产物：
  描述：

  4-碘联苯 、 1-(2H)-酞嗪酮 在 bis(tetrapropylammonium) tetraiododicuprate(I) 、 trans-1,2-cyclohexanediamine methanesulfonic acid 、 caesium carbonate 作用下， 以 1,4-二氧六环 为溶剂， 反应 24.0h， 以80%的产率得到2-([1,1'-biphenyl]-4-yl)phthalazin-1(2H)-one
  参考文献：
  名称：

  A Soluble Copper(I) Source and Stable Salts of Volatile Ligands for Copper-Catalyzed C–X Couplings

  摘要：

  A stable adduct of Cul with Bu4NI, soluble in organic solvents, has been identified as an effective catalyst for copper-catalyzed C-N and C-O couplings. In addition, stable nonhygroscopic salts of some high performance ligands (diamine MsOH salts/CuX and copper(II) diketonates) were shown to be of similar and sometimes greater reactivity compared to the literature reagents for these couplings. Furthermore, these more robust conditions result in more reproducible results.

  DOI：

  10.1021/jo300905w

文献信息

• A Soluble Copper(I) Source and Stable Salts of Volatile Ligands for Copper-Catalyzed C–X Couplings
  作者：Peter E. Maligres、Shane W. Krska、Peter G. Dormer

  DOI：10.1021/jo300905w

  日期：2012.9.7

  A stable adduct of Cul with Bu4NI, soluble in organic solvents, has been identified as an effective catalyst for copper-catalyzed C-N and C-O couplings. In addition, stable nonhygroscopic salts of some high performance ligands (diamine MsOH salts/CuX and copper(II) diketonates) were shown to be of similar and sometimes greater reactivity compared to the literature reagents for these couplings. Furthermore, these more robust conditions result in more reproducible results.
• Vinylene Carbonate as Latent Formylmethyl Surrogate: The Expediency of Ruthenium(II) Catalysis in Accessing Arylacetaldehydes, Arylacetates and Acetals
  作者：Dolly David Thalakottukara、Thirumanavelan Gandhi

  DOI：10.1002/ejoc.202300847

  日期：2024.2.5

  Herein, we report a Ru(II)-catalyzed additive controlled direct formylmethylation and sequential dehydrogenative esterification of phthalazinones to access arylacetaldehydes, arylacetates, and acetals using vinylene carbonate as a C2 synthon. The reaction mechanism is elucidated using various control experiments and confirmation of possible intermediates by mass spectrometry.

  在此，我们报道了一种Ru(II)催化添加剂控制的二氮杂萘酮的直接甲酰甲基化和顺序脱氢酯化，以使用碳酸亚乙烯酯作为C2合成子来获得芳基乙醛、芳基乙酸酯和缩醛。使用各种对照实验并通过质谱法确认可能的中间体来阐明反应机理。