1-methyl-3-phenylsulfanyl-2-pyrrolidinone | 59953-50-3

• 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-methyl-3-phenylsulfanyl-2-pyrrolidinone
• 英文别名: 1-methyl-3-(phenylthio)pyrrolidin-2-one；1-Methyl-3-phenylsulfinyl-2-pyrrolidinon；1-Methyl-3-phenylthio-2-pyrrolidinon；1-methyl-3-phenylsulfanyl-pyrrolidin-2-one；2-Pyrrolidinone, 1-methyl-3-(phenylthio)-；1-methyl-3-phenylsulfanylpyrrolidin-2-one
• CAS: 59953-50-3
• 化学式: C₁₁H₁₃NOS
• 分子量: 207.296
• InChiKey: YDSVFOLUFPDABU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  45.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-methyl-3-phenylsulfanyl-2-pyrrolidinone 在 4-Methyl-2,3-difluoro-iodobenzene 作用下， 以 二氯甲烷 为溶剂， 以56%的产率得到1-methyl-2-oxo-3-phenylsulfanyl-3-pyrroline
  参考文献：
  名称：

  Studies on the additive fluoro-Pummerer reaction of phenylsulfanylated lactams with difluoroiodotoluene

  摘要：

  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.

  DOI：

  10.1016/s0040-4039(01)01813-5
• 作为产物：
  描述：

  ethyl 2-hydroxy-2-(1-methyl-2-oxopyrrolidin-3-ylidene)acetate 在 p-nitrobenzenesulfonyl azide 、 aluminum oxide 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 0.75h， 生成 1-methyl-3-phenylsulfanyl-2-pyrrolidinone
  参考文献：
  名称：

  RhII催化的X–H插入反应中不稳定N-烷基α-重氮-γ-丁内酰胺的制备和原位使用

  摘要：

  N-烷基α-重氮-γ-丁内酰胺以前被发现不稳定，并且无法进行二聚生成双hydr，已通过原位Rh II催化，立即与醇，芳族胺和硫醇成功转化为各种X–H插入产物。反应。与脂族胺或未反应的，空间受阻的苯胺相比，反应趋于产生烯胺加合物。

  DOI：

  10.3762/bjoc.16.55

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。
• Electrolytic partial fluorination of organic compounds. 6. Highly regioselective electrochemical monofluorination of aliphatic nitrogen-containing heterocycles
  作者：Akinori Konno、Wataru Naito、Toshio Fuchigami

  DOI：10.1016/s0040-4039(00)60921-8

  日期：1992.11

  regioselective eletrochemical monofluorination of α-phenylsulfenyl lactams was carried out in good chemical and current yields. This is the first successful example of anodic monofluorination of aliphatic nitrogen-containing heterocycles.

  α-苯基亚磺酰基内酰胺的高度区域选择性电化学单氟化以良好的化学和电流收率进行。这是脂肪族含氮杂环的阳极单氟化的第一个成功实例。
• Electrolytic Partial Fluorination of Organic Compounds. 33. Regioselective Anodic Monofluorination of alpha-Phenylsulfenyl Lactams and Sulfur-Containing Nitrogen Heterocycles.
  作者：Akinori Konno、Wataru Naito、Toshio Fuchigami、Dennis G. Peters、Majid Motevalli、Hiroaki Murase、Tatsuya Shono、H. Toftlund

  DOI：10.3891/acta.chem.scand.53-0887

  日期：——

  Anodic monofluorination of a variety of nitrogen heterocycles has been investigated in order to ascertain the scope and limitations of the anodic monofluorination method in the synthesis of monofluorinated nitrogen heterocycles. Electrolytic monofluorination of alpha-(phenylsulfenyl)lactams proceeded effectively, and the regiochemistry and efficiency of the reaction were greatly dependent on the molecular structure (ring size, substitution on the nitrogen atom, etc.) of the lactams. The high yields of monofluorinated lactams observed here are of great synthetic value because the phenylsulfenyl group is known to be easily removed oxidatively and/or reductively.
• GUZMAN A.; MUCHOWSKI J. M.; SALDANA J., CHEM. AND IND. <CHIN-AG>, 1977, NO 9, 357-358
  作者：GUZMAN A.、 MUCHOWSKI J. M.、 SALDANA J.

  DOI：——

  日期：——
• ZORETIC P. A.; SOJA P.; SINHA N. D., J. ORG. CHEM. <JOCE-AH>, 1978, 43, NO 7, 1379-1382
  作者：ZORETIC P. A.、 SOJA P.、 SINHA N. D.

  DOI：——

  日期：——