1-(4-fluorophenylthio)octan-2-ol | 1174708-92-9

• 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-(4-fluorophenylthio)octan-2-ol
• 英文别名: gwx-920；1-(4-Fluorophenyl)sulfanyloctan-2-ol
• CAS: 1174708-92-9
• 化学式: C₁₄H₂₁FOS
• 分子量: 256.385
• InChiKey: NYABYEZEJAYCFN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  45.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-氟-4-[(4-氟苯基)二硫烷基]苯 、 1,2-环氧辛烷 在 Rongalite 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.08h， 以91%的产率得到1-(4-fluorophenylthio)octan-2-ol
  参考文献：
  名称：

  Rongalite® promoted highly regioselective synthesis of β-hydroxy sulfides by ring opening of epoxides with disulfides

  摘要：

  Rongaliteo (R) promotes cleavage of disulfides generating thiolate anions that then undergo facile ring opening of epoxides in the presence of K2CO3 to afford alpha-addition products 3 with good to excellent yields. The important features of this methodology are broad substrates scope, high yielding, reasonably rapid reaction rate, high regioselectivity and no requirement of metal catalysts. It should be noted that the thiolate anion attacks the epoxides derived from styrene to produce the corresponding alpha-addition products 3 with high regioselectivity, instead of the beta-addition regioisomer 4 that Could be formed from the attack of the nucleophile at the benzylic position. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.04.085

文献信息

• Rongalite® promoted highly regioselective synthesis of β-hydroxy sulfides by ring opening of epoxides with disulfides
  作者：Wenxue Guo、Jiuxi Chen、Dengze Wu、Jinchang Ding、Fan Chen、Huayue Wu

  DOI：10.1016/j.tet.2009.04.085

  日期：2009.7

  Rongaliteo (R) promotes cleavage of disulfides generating thiolate anions that then undergo facile ring opening of epoxides in the presence of K2CO3 to afford alpha-addition products 3 with good to excellent yields. The important features of this methodology are broad substrates scope, high yielding, reasonably rapid reaction rate, high regioselectivity and no requirement of metal catalysts. It should be noted that the thiolate anion attacks the epoxides derived from styrene to produce the corresponding alpha-addition products 3 with high regioselectivity, instead of the beta-addition regioisomer 4 that Could be formed from the attack of the nucleophile at the benzylic position. (C) 2009 Elsevier Ltd. All rights reserved.