2,4-dibromoquinoline-3-carbaldehyde | 532392-87-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2,4-dibromoquinoline-3-carbaldehyde
• 英文别名: 2,4-dibromo-3-quinolinecarboxaldehyde；2,4-Dibromoquinoline-3-carboxaldehyde
• CAS: 532392-87-3
• 化学式: C₁₀H₅Br₂NO
• 分子量: 314.964
• InChiKey: PSSFBANKPZRHIQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  30
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,4-dibromoquinoline-3-carbaldehyde 在 bis-triphenylphosphine-palladium(II) chloride N-甲基哌嗪 、 copper(l) iodide 、 正丁基锂 、 TEA 作用下， 以 四氢呋喃 为溶剂， 反应 4.5h， 生成 2,4-bis(trimethylsilanylethynyl)quinoline-3-carboxaldehyde
  参考文献：
  名称：

  Regioselective lithium–halogen exchange and palladium-catalyzed cross-coupling reactions of 2,4-dihaloquinolines

  摘要：

  Lithium-halogen exchange of 2,4-dibromoquinolines proceeds regioselectively at C-4 and affords 4-substituted quinolines on quenching with electrophiles. Palladium-catalyzed cross-coupling reactions of 2-bromo-4-iodoquinoline provide 4-substituted 2-bromoquinoline derivatives. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.07.137
• 作为产物：
  描述：

  2,4-二溴喹啉 、 N,N-二甲基甲酰胺 在 正丁基锂 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.5h， 以78%的产率得到2,4-dibromoquinoline-3-carbaldehyde
  参考文献：
  名称：

  Regioselective Sonogashira Couplings of 2,4-Dibromoquinolines. A Correction

  摘要：

  Heteronuclear multiple bond correlation (HMBC) was used to determine the regiochemical outcome of palladium-catalyzed carbon-carbon bond formation between 2,4-dibromoquinolines and terminal acetylenes. The observed regioselectivity of these coupling reactions is opposite to that reported in the literature for analogous reactions.

  DOI：

  10.1021/jo034122w

文献信息

• Regioselective lithium–halogen exchange and palladium-catalyzed cross-coupling reactions of 2,4-dihaloquinolines
  作者：Daniel L. Comins、Jason M. Nolan、Ibrahim D. Bori

  DOI：10.1016/j.tetlet.2005.07.137

  日期：2005.9

  Lithium-halogen exchange of 2,4-dibromoquinolines proceeds regioselectively at C-4 and affords 4-substituted quinolines on quenching with electrophiles. Palladium-catalyzed cross-coupling reactions of 2-bromo-4-iodoquinoline provide 4-substituted 2-bromoquinoline derivatives. (c) 2005 Elsevier Ltd. All rights reserved.
• Regioselective Sonogashira Couplings of 2,4-Dibromoquinolines. A Correction
  作者：Jason M. Nolan、Daniel L. Comins

  DOI：10.1021/jo034122w

  日期：2003.5.1

  Heteronuclear multiple bond correlation (HMBC) was used to determine the regiochemical outcome of palladium-catalyzed carbon-carbon bond formation between 2,4-dibromoquinolines and terminal acetylenes. The observed regioselectivity of these coupling reactions is opposite to that reported in the literature for analogous reactions.