(3E)-2-(2'-tetrahydrofuranyl)oct-3-enal

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧唑烯
• 英文名称: (3E)-2-(2'-tetrahydrofuranyl)oct-3-enal
• 英文别名: (E,2R)-2-[(2S)-oxolan-2-yl]oct-3-enal
• 化学式: C₁₂H₂₀O₂
• 分子量: 196.29
• InChiKey: PNAUQFJTTOIZIK-YILIYONBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  tetrahydro-2-(2-propyn-1-yloxy)-furan 在 Lindlar's catalyst aluminum tris(2,6-diphenylphenoxide) 、 喹啉 、 正丁基锂 、 氢气 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 二氯甲烷 、 乙酸乙酯 为溶剂， -78.0~20.0 ℃ 、101.33 kPa 条件下， 反应 14.0h， 生成 (3E)-2-(2'-tetrahydrofuranyl)oct-3-enal
  参考文献：
  名称：

  Regio- and Stereoselective Ferrier Reaction of O-1,3-Dienyl Acetals Promoted by Organoaluminum Complexes

  摘要：

  The Ferrier reaction of O-1,3-dienyl acetals promoted by organoaluminum complexes such as methylaluminum bis(2,6-di-tert-butyl-4-methylphenoxide) (MAD) is shown to proceed with a high degree of regio- and stereoselectivity to afford the corresponding alpha-alkenyl-substituted beta-alkoxy aldehydes in good yields. The mechanistic origin of the high regiocontrolling ability of MAD is elucidated. This method, coupled with the easy availability of the requisite substrates, expands the synthetic scope of the Ferrier reaction.

  DOI：

  10.1021/ol062042j

文献信息

• Regio- and Stereoselective Ferrier Reaction of <i>O</i>-1,3-Dienyl Acetals Promoted by Organoaluminum Complexes
  作者：Eiji Tayama、Wataru Isaka

  DOI：10.1021/ol062042j

  日期：2006.11.1

  The Ferrier reaction of O-1,3-dienyl acetals promoted by organoaluminum complexes such as methylaluminum bis(2,6-di-tert-butyl-4-methylphenoxide) (MAD) is shown to proceed with a high degree of regio- and stereoselectivity to afford the corresponding alpha-alkenyl-substituted beta-alkoxy aldehydes in good yields. The mechanistic origin of the high regiocontrolling ability of MAD is elucidated. This method, coupled with the easy availability of the requisite substrates, expands the synthetic scope of the Ferrier reaction.