4-(p-fluorophenylthio)octan-2-one | 1224975-71-6

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 4-(p-fluorophenylthio)octan-2-one
• CAS: 1224975-71-6
• 化学式: C₁₄H₁₉FOS
• 分子量: 254.369
• InChiKey: ACYZFWAIXXAVOM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.46
• 重原子数：
  17.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  3-辛烯-2-酮 、 1-氟-4-[(4-氟苯基)二硫烷基]苯 在 rongalite 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.17h， 以84%的产率得到4-(p-fluorophenylthio)octan-2-one
  参考文献：
  名称：

  Rongalite® and base-promoted cleavage of disulfides and subsequent Michael addition to α,β-unsaturated ketones/esters: an odorless synthesis of β-sulfido carbonyl compounds

  摘要：

  A highly practical method to access beta-sulfido carbonyl compounds was developed, which could be conducted without any expensive reagent, special apparatus/technique, and no requirement of metal catalysts. beta-Sulfido carbonyl compounds were formed at room temperature, in short time and with high chemoselectivity in good to excellent yields. A plausible mechanism for the role of Rongalite (R), as a promoter for the cleavage of disuffides generating thiolate anions that then undergo facile thia-Michael addition to alpha,beta-unsaturated ketones and esters is proposed. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.02.001

文献信息

• Rongalite® and base-promoted cleavage of disulfides and subsequent Michael addition to α,β-unsaturated ketones/esters: an odorless synthesis of β-sulfido carbonyl compounds
  作者：Wenxue Guo、Guangshu Lv、Jiuxi Chen、Wenxia Gao、Jinchang Ding、Huayue Wu

  DOI：10.1016/j.tet.2010.02.001

  日期：2010.3

  A highly practical method to access beta-sulfido carbonyl compounds was developed, which could be conducted without any expensive reagent, special apparatus/technique, and no requirement of metal catalysts. beta-Sulfido carbonyl compounds were formed at room temperature, in short time and with high chemoselectivity in good to excellent yields. A plausible mechanism for the role of Rongalite (R), as a promoter for the cleavage of disuffides generating thiolate anions that then undergo facile thia-Michael addition to alpha,beta-unsaturated ketones and esters is proposed. (C) 2010 Elsevier Ltd. All rights reserved.