1-n-butyl-3-fluoro-3-phenylsulfanylazetidin-2-one | 149948-97-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: 1-n-butyl-3-fluoro-3-phenylsulfanylazetidin-2-one
• 英文别名: 2-Azetidinone, 1-butyl-3-fluoro-3-(phenylthio)-；1-butyl-3-fluoro-3-phenylsulfanylazetidin-2-one
• CAS: 149948-97-0
• 化学式: C₁₃H₁₆FNOS
• 分子量: 253.341
• InChiKey: CLHSHFMIEASBDD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  45.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-n-butyl-3-phenylsulfinylazetidin-2-one 在 triethylamine tris(hydrogen fluoride) 作用下， 以 乙腈 为溶剂， 以92%的产率得到1-n-butyl-3-fluoro-3-phenylsulfanylazetidin-2-one
  参考文献：
  名称：

  Electrolytic partial fluorination of organic compounds. 8. Highly regioselective anodic monofluorination of β-lactams

  摘要：

  Anodic partial fluorination of beta-lactams has been performed for the first time. Alpha-Phenylsulfenyl beta-lactams were monofluorinated highly regioselectively in excellent yields and with high current efficiencies, and this anodic method is superior to conventional chemical methods.

  DOI：

  10.1021/jo00068a010

文献信息

• Fluorination of sulfanyl amides using difluoroiodoarene reagents
  作者：William B. Motherwell、Michael F. Greaney、Jeremy J. Edmunds、Jonathan W. Steed

  DOI：10.1039/b209078c

  日期：2002.12.19

  A range of sulfur-containing amides have been fluorinated with the hypervalent iodine difluoride reagents 1, and two principal reaction pathways identified. Cephalosporin esters 2 having a heteroatom in the α-position to sulfur undergo fluorination in DCM with cleavage of the carbon–sulfur bond to form novel fluorinated β-lactams 4. Sulfides with electron-withdrawing groups in the α-position undergo α-fluorination in a process analogous to the classical Pummerer reaction. This Fluoro-Pummerer reaction has been exemplified for a range of simple α-phenylsulfanylacetamides 14–19. When β-hydrogens are present in the substrate a different route is followed, with deprotonation by basic fluoride taking place to yield vinyl sulfides 41–43. When an excess of the fluorinating reagent is used these vinyl sulfides can undergo further reaction in a novel tandem Pummerer-Additive-Pummerer process to yield α,β-difluoro sulfides 45–47.

  使用高价二氟化碘试剂 1 对一系列含硫酰胺进行了氟化处理，并确定了两种主要的反应途径。头孢菌素酯 2 在硫的α位上有一个杂原子，在二氯甲烷中发生氟化反应，碳-硫键断裂，形成新型氟化β-内酰胺 4。在 α 位上带有抽电子基团的硫化物在类似于经典普默尔反应的过程中发生 α-氟化反应。这种氟-普默尔反应已在一系列简单的 α-苯硫基乙酰胺 14-19 中得到验证。当底物中含有 β 氢时，则采用不同的途径，通过碱性氟化物进行去质子化反应，生成乙烯基硫化物 41-43。当使用过量的氟化试剂时，这些乙烯基硫化物可在新型串联式普默尔-添加剂-普默尔工艺中发生进一步反应，生成 α,β-二氟硫化物 45-47。
• Narizuka Satoru, Fuchigami Toshio, J. Org. Chem., 58 (1993) N 16, S 4200-4201
  作者：Narizuka Satoru, Fuchigami Toshio

  DOI：——

  日期：——
• Studies on the additive fluoro-Pummerer reaction of phenylsulfanylated lactams with difluoroiodotoluene
  作者：Michael F Greaney、William B Motherwell、Derek A Tocher

  DOI：10.1016/s0040-4039(01)01813-5

  日期：2001.11

  Two fluorine atoms are effectively introduced to the 3- and 4-positions of sulfur-containing lactams through the action of the hypervalent iodoarene reagent difluoroiodotoluene (DFIT). The reaction proceeds through the intermediacy of the isolable alpha-beta -unsaturated congener followed by an additive-Pummerer process. (C) 2001 Elsevier Science Ltd. All rights reserved.
• JPH06263724A
  申请人：——

  公开号：JPH06263724A

  公开（公告）日：1994-09-20
• Electrolytic partial fluorination of organic compounds. 8. Highly regioselective anodic monofluorination of β-lactams
  作者：Satoru Narizuka、Toshio Fuchigami

  DOI：10.1021/jo00068a010

  日期：1993.7

  Anodic partial fluorination of beta-lactams has been performed for the first time. Alpha-Phenylsulfenyl beta-lactams were monofluorinated highly regioselectively in excellent yields and with high current efficiencies, and this anodic method is superior to conventional chemical methods.