4-Chloro-2-(furan-2-yl)pyridine-3-carbaldehyde | 1265175-32-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 4-Chloro-2-(furan-2-yl)pyridine-3-carbaldehyde
• 英文别名: 4-chloro-2-(furan-2-yl)pyridine-3-carbaldehyde
• CAS: 1265175-32-3
• 化学式: C₁₀H₆ClNO₂
• 分子量: 207.616
• InChiKey: GMWBOWXSXPPAMN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  43.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-(三丁基锡烷基)呋喃 、 2,4-二氯烟醛 在 bis-triphenylphosphine-palladium(II) chloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 以64%的产率得到4-Chloro-2-(furan-2-yl)pyridine-3-carbaldehyde
  参考文献：
  名称：

  Reactivity and regioselectivity in Stille couplings of 3-substituted 2,4-dichloropyridines

  摘要：

  The influence of substituents at C-3 of 2,4-dichloropyridines on their reactivity and regioselectivity in Pd-catalyzed cross-couplings is studied. As a model reaction, the (Ph3P)(2)PdCl2-catalyzed Stille coupling between 2-furyl(tributyl)tin and pyridines is chosen. Increased electron-withdrawing ability of a substituent at the pyridine 3-position improves the overall reactivity. Absolute selectivity for coupling at C-2 is achieved with an amino group at C-3, and the selectivity is totally reversed when the amino group is exchanged for a nitro substituent. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.11.108

文献信息

• Reactivity and regioselectivity in Stille couplings of 3-substituted 2,4-dichloropyridines
  作者：Abhijit Datta Khoje、Lise-Lotte Gundersen

  DOI：10.1016/j.tetlet.2010.11.108

  日期：2011.1

  The influence of substituents at C-3 of 2,4-dichloropyridines on their reactivity and regioselectivity in Pd-catalyzed cross-couplings is studied. As a model reaction, the (Ph3P)(2)PdCl2-catalyzed Stille coupling between 2-furyl(tributyl)tin and pyridines is chosen. Increased electron-withdrawing ability of a substituent at the pyridine 3-position improves the overall reactivity. Absolute selectivity for coupling at C-2 is achieved with an amino group at C-3, and the selectivity is totally reversed when the amino group is exchanged for a nitro substituent. (C) 2010 Elsevier Ltd. All rights reserved.