5-(sec-butyl)furan-2-carbaldehyde | 1268242-43-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-(sec-butyl)furan-2-carbaldehyde
• 英文别名: 5-Butan-2-ylfuran-2-carbaldehyde；5-butan-2-ylfuran-2-carbaldehyde
• CAS: 1268242-43-8
• 化学式: C₉H₁₂O₂
• 分子量: 152.193
• InChiKey: ZJNXEXUNRLHHKE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  30.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  5-碘-2-呋喃甲醛 、 2-碘丁烷 在 锌 、 α,α,α-三联吡啶 、 nickel dichloride 作用下， 以 四氢呋喃 为溶剂， 反应 22.0h， 以71%的产率得到5-(sec-butyl)furan-2-carbaldehyde
  参考文献：
  名称：

  Nickel-Catalyzed Negishi Cross-Coupling Reactions of Secondary Alkylzinc Halides and Aryl Iodides

  摘要：

  A general Ni-catalyzed process for the cross-coupling of secondary alkylzinc halides and aryl/heteroaryl iodides has been developed. This is the first process to overcome the isomerization and beta-hydride elimination problems that are associated with the use of secondary nucleophiles, and that have limited the analogous Pd-catalyzed systems. The impact of salt additives was also investigated. It was found that the presence of LiBF4 dramatically improves both isomeric retention and yield for challenging substrates.

  DOI：

  10.1021/ol200098d

文献信息

• Nickel-Catalyzed Negishi Cross-Coupling Reactions of Secondary Alkylzinc Halides and Aryl Iodides
  作者：Amruta Joshi-Pangu、Madhu Ganesh、Mark R. Biscoe

  DOI：10.1021/ol200098d

  日期：2011.3.4

  A general Ni-catalyzed process for the cross-coupling of secondary alkylzinc halides and aryl/heteroaryl iodides has been developed. This is the first process to overcome the isomerization and beta-hydride elimination problems that are associated with the use of secondary nucleophiles, and that have limited the analogous Pd-catalyzed systems. The impact of salt additives was also investigated. It was found that the presence of LiBF4 dramatically improves both isomeric retention and yield for challenging substrates.