2-(3,5-dimethylphenyl)-1-phthalazinone

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 2-(3,5-dimethylphenyl)-1-phthalazinone
• 英文别名: 2-(3,5-dimethylphenyl)phthalazin-1(2H)-one；2-(3,5-Dimethylphenyl)-1,2-dihydrophthalazin-1-one；2-(3,5-dimethylphenyl)phthalazin-1-one
• 化学式: C₁₆H₁₄N₂O
• 分子量: 250.3
• InChiKey: LPQGFKNUGGDQHT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 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-(3,5-dimethylphenyl)-1-phthalazinone 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63 %的产率得到2-(2,4-dimethyl-6-(1-oxophthalazin-2(1H)-yl)phenyl)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：

  1,3-二甲基-5-碘苯 、 1-(2H)-酞嗪酮 在 copper(l) iodide 、 (1S,2S)-(+)-1,2-环己二胺 、 caesium carbonate 作用下， 以 1,4-二氧六环 、 十二烷 为溶剂， 反应 24.0h， 以90%的产率得到2-(3,5-dimethylphenyl)-1-phthalazinone
  参考文献：
  名称：

  一种通用且有效的铜催化剂，用于芳基卤化物的酰胺化和氮杂环的N-芳基化。

  摘要：

  DOI：

  10.1021/ja016226z

文献信息

• Palladium-Catalyzed Phthalazinone Synthesis Using Paraformaldehyde as Carbon Source
  作者：Huamin Wang、Jinhui Cai、Huawen Huang、Guo-Jun Deng

  DOI：10.1021/ol502498y

  日期：2014.10.17

  A palladium-catalyzed one-pot synthesis of phthalazinones from 2-halomethyl benzoates, paraformaldehyde, and aryl hydrazines is described. Various substituted phthalazinones were selectively obtained in good yields using paraformaldehyde as the cheap carbon source (CH).
• COPPER-CATALYZED FORMATION OF CARBON-HETEROATOM AND CARBON-CARBON BONDS
  申请人：MASSACHUSETTS INSTITUTE OF TECHNOLOGY

  公开号：EP1390340A1

  公开（公告）日：2004-02-25
• EP1390340A4
  申请人：——

  公开号：EP1390340A4

  公开（公告）日：2007-07-25
• [EN] COPPER-CATALYZED FORMATION OF CARBON-HETEROATOM AND CARBON-CARBON BONDS<br/>[FR] FORMATION PAR CATALYSE DE CUIVRE DE LIAISONS CARBONE-HETEROATOME ET CARBONE-CARBONE
  申请人：MASSACHUSETTS INST TECHNOLOGY

  公开号：WO2002085838A1

  公开（公告）日：2002-10-31

  The present invention relaters to copper-catalyzed carbon-heteroatom and carbon-carbon bond-forming methods. In certain embodiments, the present invention relates to copper-catalyzed methods of forming a carbon-nitrogen bond between the nitrogen atom of an amide or amine moiety and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. In additional embodiments, the present invention relates to cooper-catalyzed methods of forming a carbon-nitrogen bond between a nitrogen atom of an acyl hydrazine and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. In other embodiments, the present invention relates to copper-catalyzed methods of forming a carbon-nitrogen bond between the nitrogen atom of a nitrogen-containing heteroaromatic, e.g., indole, pyrazole, and indazole, and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. In certain embodiments, the present invention relates to copper-catalyzed methods of forming a carbon-oxygen bond between the oxygen atom of an alcohol and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. The present invention also relates to copper-catalyzed methods of forming a carbon-carbon bond between a reactant comprising a nucleophilic carbon atom, e.g., an enolate or malonate anion, and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. Importantly, all the methods of the present invention are relatively inexpensive to practice due to the low cost of the copper comprised by the catalysts.
• A General and Efficient Copper Catalyst for the Amidation of Aryl Halides and the <i>N</i>-Arylation of Nitrogen Heterocycles
  作者：Artis Klapars、Jon C. Antilla、Xiaohua Huang、Stephen L. Buchwald

  DOI：10.1021/ja016226z

  日期：2001.8.1