1,2-hexene oxide

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 1,2-hexene oxide
• 英文别名: 1-(4-Methylphenyl)sulfanylhexan-2-ol
• 化学式: C₁₃H₂₀OS
• 分子量: 224.367
• InChiKey: GMMKBDBZOJWFHV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  45.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  丁基环氧乙烷 、 4-甲苯硫酚 在 iododioxobis(triphenylphosphine)rhenium(V) 作用下， 以 乙酸乙酯 为溶剂， 以95%的产率得到1,2-hexene oxide
  参考文献：
  名称：

  Addition of unactivated thiols to epoxides and oxetanes catalyzed by a rhenium-oxo complex

  摘要：

  A method for synthesizing beta- and gamma-hydroxy thioethers via addition of unactivated thiols to epoxides and oxetanes has been developed. This reaction is proposed to proceed through an unconventional mode of activation of the heterocycles. The transformation is catalyzed by ReO2I(PPh3)(2) affording beta- and gamma-hydroxy thioethers in moderate to excellent yield with excellent regioselectivity. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.catcom.2014.01.005

文献信息

• The Generation of (Samarium) Thiolates from Aryl Thiocyanates and Their Reaction with Epoxides: A Route to β-Hydroxy Sulfides
  作者：Ian W.J. Still、L. James、L.J.P. Martyn

  DOI：10.1080/00032719808006491

  日期：1998.3.1

  This investigation describes the reduction of an aryl thiocyanate with samarium(II) iodide, followed by reaction with various epoxides, to produce beta-hydroxy sulfides. This method of ring opening of epoxides provides a substantial improvement in reaction time and convenience over existing methods while maintaining good regioselectivity and excellent yield.