2-phenylthioacetylbutylamide | 71433-00-6

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-phenylthioacetylbutylamide
• 英文别名: N-butyl(phenylsulfanyl)acetamide；N-butyl-2-phenylsulfanylacetamide
• CAS: 71433-00-6
• 化学式: C₁₂H₁₇NOS
• 分子量: 223.339
• InChiKey: RGLKVTROGVNRBI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-phenylthioacetylbutylamide 以37%的产率得到
  参考文献：
  名称：

  HIRAI K.; IWANO Y., TETRAHEDRON LETT., 1979, NO 22, 2031-2034

  摘要：

  DOI：
• 作为产物：
  描述：

  S-phenyl 2-bromoethanethioate 、 正丁胺 在 sodium hydroxide 作用下， 以 1,4-二氧六环 为溶剂， 反应 0.17h， 以88%的产率得到2-phenylthioacetylbutylamide
  参考文献：
  名称：

  Regioselective synthesis of inhibitors of histone acetyl transferase covalently linking spermidine to the s-terminus of coenzyme a and fragments.

  摘要：

  The reaction of a bromoacetylthioester BrCH2CO-S-R (R radical in the coenzyme A series) with spermidine (Spd) derivatives is investigated and it is established that the adduct SpdCOCH2-S-R 1 is the product of the reaction. Parallel studies with model compounds show that this is a general reaction of bromoacetylthioesters. The synthesis of analogs of 1 is described and they correspond to inhibitors of the histone acetyltransferase.

  DOI：

  10.1016/s0040-4020(01)80153-8

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。
• Studies on the oxidation and fluorination of α-phenylsulfanylacetamides using difluoroiodotoluene
  作者：Michael F Greaney、William B Motherwell

  DOI：10.1016/s0040-4039(00)00617-1

  日期：2000.6

  alpha-Phenylsulfanylacetamides are fluorinated in the alpha-position when treated with difluoroiodotoluene (DFIT) in a fluoro-Pummerer reaction. For N-phenyl amides an intramolecular Friedel-Crafts reaction may compete and produce heterocycles. (C) 2000 Elsevier Science Ltd. All rights reserved.