(2SR,3RS)-5-butoxy-2-tert-butyl-3-vinyl-tetrahydrofuran

• 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: (2SR,3RS)-5-butoxy-2-tert-butyl-3-vinyl-tetrahydrofuran
• 英文别名: (2S,3R)-5-butoxy-2-tert-butyl-3-ethenyloxolane
• 化学式: C₁₄H₂₆O₂
• 分子量: 226.359
• InChiKey: WNQBZYBCKJVKSM-RXTYADHFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2SR,3RS)-5-butoxy-2-tert-butyl-3-vinyl-tetrahydrofuran 在 铬酸 作用下， 生成 (4S,5R)-5-tert-Butyl-4-vinyl-dihydro-furan-2-one
  参考文献：
  名称：

  Stereoselective Synthesis of Furans by the Pd-Catalyzed Oshima−Utimoto Reaction

  摘要：

  The Pd-catalyzed coupling of acyclic allylic alcohols with vinyl ethers was examined and found to proceed with 2.5-10 mol % of catalyst and to provide cyclic acetals with good stereoselection. The reaction is tolerant of a number of functional groups and can be used to generate quaternary centers in a stereoselective fashion.

  DOI：

  10.1021/ol051275s
• 作为产物：
  描述：

  乙烯基正丁醚 、 (E)-2,2-dimethylhex-4-en-3-ol 在 palladium diacetate copper diacetate 作用下， 以 乙腈 为溶剂， 反应 15.0h， 以36%的产率得到(2SR,3RS)-5-butoxy-2-tert-butyl-3-vinyl-tetrahydrofuran
  参考文献：
  名称：

  Stereoselective Synthesis of Furans by the Pd-Catalyzed Oshima−Utimoto Reaction

  摘要：

  The Pd-catalyzed coupling of acyclic allylic alcohols with vinyl ethers was examined and found to proceed with 2.5-10 mol % of catalyst and to provide cyclic acetals with good stereoselection. The reaction is tolerant of a number of functional groups and can be used to generate quaternary centers in a stereoselective fashion.

  DOI：

  10.1021/ol051275s

文献信息

• Stereoselective Synthesis of Furans by the Pd-Catalyzed Oshima−Utimoto Reaction
  作者：Michael A. Evans、James P. Morken

  DOI：10.1021/ol051275s

  日期：2005.7.1

  The Pd-catalyzed coupling of acyclic allylic alcohols with vinyl ethers was examined and found to proceed with 2.5-10 mol % of catalyst and to provide cyclic acetals with good stereoselection. The reaction is tolerant of a number of functional groups and can be used to generate quaternary centers in a stereoselective fashion.