2-(2-methylpyrimidin-5-yl)benzaldehyde

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 2-(2-methylpyrimidin-5-yl)benzaldehyde
• 英文别名: 2-(2-Methylpyrimidin-5-yl)benzaldehyde
• 化学式: C₁₂H₁₀N₂O
• 分子量: 198.224
• InChiKey: XOXMCNIEPBRFNO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  42.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-甲基-5-溴嘧啶 、 2-甲酰基苯硼酸 在 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 甲醇 、 乙二醇二甲醚 、 水 为溶剂， 以82%的产率得到2-(2-methylpyrimidin-5-yl)benzaldehyde
  参考文献：
  名称：

  Palladium-Catalyzed meta-C–H Olefination of Arene-Tethered Diols Directed by Well-Designed Pyrimidine-Based Group

  摘要：

  The palladium-catalyzed meta-olefination of arene-tethered diols attached to a well-designed pyrimidine moiety is presented. Applications of the protocol are illustrated by the synthesis of various diol-based natural products, such as coumarins, phenylpropanoids, stilbenes, and chalcones. Advantages of this method are demonstrated through the easy removal of the template and a gram-scale olefination reaction. Finally, experimental verification, including H-1 NMR, ESI-MS and IR, and DFT studies are undertaken to elucidate the mechanistic complexity.

  DOI：

  10.1021/acs.orglett.9b00433

文献信息

• Palladium-Catalyzed <i>meta</i>-C–H Olefination of Arene-Tethered Diols Directed by Well-Designed Pyrimidine-Based Group
  作者：Siqiang Fang、Xiaobing Wang、Fucheng Yin、Pei Cai、Huali Yang、Lingyi Kong

  DOI：10.1021/acs.orglett.9b00433

  日期：2019.3.15

  The palladium-catalyzed meta-olefination of arene-tethered diols attached to a well-designed pyrimidine moiety is presented. Applications of the protocol are illustrated by the synthesis of various diol-based natural products, such as coumarins, phenylpropanoids, stilbenes, and chalcones. Advantages of this method are demonstrated through the easy removal of the template and a gram-scale olefination reaction. Finally, experimental verification, including H-1 NMR, ESI-MS and IR, and DFT studies are undertaken to elucidate the mechanistic complexity.