4-((4-fluorophenyl)thio)-4-phenylbutan-2-one | 1224975-55-6

• 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-((4-fluorophenyl)thio)-4-phenylbutan-2-one
• 英文别名: 4-(p-fluorophenylthio)-4-phenylbutan-2-one；4-(4-Fluorophenyl)sulfanyl-4-phenylbutan-2-one；4-(4-fluorophenyl)sulfanyl-4-phenylbutan-2-one
• CAS: 1224975-55-6
• 化学式: C₁₆H₁₅FOS
• 分子量: 274.359
• InChiKey: BBKKTWOUYATDBM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 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 、 苄叉丙酮 在 rongalite 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.17h， 以83%的产率得到4-((4-fluorophenyl)thio)-4-phenylbutan-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

• Synthesis of β-sulfanyl ketones via a tandem rearrangement-conjugate addition reaction catalyzed by a Re(V)-oxo complex
  作者：Alyson E. Garst、Alexandra D. Badiceanu、Kristine A. Nolin

  DOI：10.1016/j.tetlet.2012.11.047

  日期：2013.2

  A method for synthesizing β-sulfanyl ketones via a tandem rearrangement and conjugate addition reaction has been developed. This methodology provides access to a range of β-sulfanyl ketones through the rearrangement of propargyl alcohols to the corresponding enones followed by the conjugate addition of unactivated thiols. The one-pot, tandem transformation is catalyzed by ReOCl3(OPPh3)(S(CH3)2) affording

  已经开发了通过串联重排和共轭加成反应合成β-硫烷基酮的方法。通过将炔丙醇重排成相应的烯酮，然后共轭添加未活化的硫醇，该方法学提供了一系列β-硫烷基酮的途径。通过ReOCl 3（OPPh 3）（S（CH 3）2）催化一锅串联转化，可提供高收率的芳基和烷基β-硫烷基酮。
• 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.