2-(n-butyl)-2-(1'-iodoethenyl)tetrahydrofuran | 1094490-31-9

• 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: 2-(n-butyl)-2-(1'-iodoethenyl)tetrahydrofuran
• 英文别名: 2-Butyl-2-(1-iodoethenyl)oxolane
• CAS: 1094490-31-9
• 化学式: C₁₀H₁₇IO
• 分子量: 280.149
• InChiKey: IBUZQDYKEOBJOZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  4-vinylideneoctan-1-ol 在 碘 作用下， 以 正己烷 为溶剂， 反应 1.0h， 以84%的产率得到2-(n-butyl)-2-(1'-iodoethenyl)tetrahydrofuran
  参考文献：
  名称：

  Highly Regio- and Stereoselective Cyclic Iodoetherification of 4,5-Alkadienols. An Efficient Preparation of 2-(1′(Z)-Iodoalkenyl)tetrahydrofurans

  摘要：

  In this paper, an efficient way to synthesize 2-(1'(Z)-iodoalkenyl)tetrahydrofurans from 4,5-alkadienols and 12 was developed. The reaction of the 4,5-allenols with a substituent in the 3-position afforded the trans-2,3-disubstituted tetrahydrofurans with very high diastereoselectivity. However, when the axially optically active 4,5-allenol was treated with 12 in n-hexane, the efficiency for chirality transfer was low. This problem was circumvented by conducting the reaction in CH2Cl2 at room temperature and applying N-iodosuccinimide as the electrophilic reagent; however, the Z/E ratio for the products is much lower. Highly optically active Z-products may be prepared via the kinetic resolution via a Sonogashira coupling reaction with propargyl alcohol.

  DOI：

  10.1021/jo802079b