5-methyl-4-({2-[(1S)-1-(methylthio)ethyl]phenyl}seleno)dihydrofuran-2(3H)-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 5-methyl-4-({2-[(1S)-1-(methylthio)ethyl]phenyl}seleno)dihydrofuran-2(3H)-one
• 化学式: C₁₄H₁₈O₂SSe
• 分子量: 329.322
• InChiKey: YXHJSSBZLFYUFS-QUNCOHTASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.56
• 重原子数：
  18.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  3-戊烯酸 、 di-2-[(1S)-1-(methylthio)ethyl]phenyl diselenide 在 溴 、 silver trifluoromethanesulfonate 作用下， 以 四氢呋喃 、 四氯化碳 为溶剂， 反应 2.58h， 以87%的产率得到5-methyl-4-({2-[(1S)-1-(methylthio)ethyl]phenyl}seleno)dihydrofuran-2(3H)-one
  参考文献：
  名称：

  A sulfur-containing diselenide as an efficient chiral reagent in asymmetric selenocyclization reactions

  摘要：

  Treatment of the di-2-[(IS)-1-(methylthio)ethyl]phenyl diselenide with bromine and silver triflate afforded the corresponding selenyl triflate which was used in situ as a strongly electrophilic selenium reagent to effect the asymmetric synthesis of oxygen- or nitrogen-containing heterocycles. Cyclic ethers, lactones, lactams or N-protected pyrrolidines have been prepared in good yield with complete regioselectivity and high diastereoselectivity. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00248-8

文献信息

• A sulfur-containing diselenide as an efficient chiral reagent in asymmetric selenocyclization reactions
  作者：Marcello Tiecco、Lorenzo Testaferri、Francesca Marini、Silvia Sternativo、Luana Bagnoli、Claudio Santi、Andrea Temperini

  DOI：10.1016/s0957-4166(01)00248-8

  日期：2001.6

  Treatment of the di-2-[(IS)-1-(methylthio)ethyl]phenyl diselenide with bromine and silver triflate afforded the corresponding selenyl triflate which was used in situ as a strongly electrophilic selenium reagent to effect the asymmetric synthesis of oxygen- or nitrogen-containing heterocycles. Cyclic ethers, lactones, lactams or N-protected pyrrolidines have been prepared in good yield with complete regioselectivity and high diastereoselectivity. (C) 2001 Elsevier Science Ltd. All rights reserved.