1-Phenyl-3-phenylsulfanyl-1,3-dihydro-indol-2-one | 193815-35-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 1-Phenyl-3-phenylsulfanyl-1,3-dihydro-indol-2-one
• 英文别名: 2H-Indol-2-one, 1,3-dihydro-1-phenyl-3-(phenylthio)-；1-phenyl-3-phenylsulfanyl-3H-indol-2-one
• CAS: 193815-35-9
• 化学式: C₂₀H₁₅NOS
• 分子量: 317.411
• InChiKey: POHARTXEXMXOEK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 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-Phenyl-3-phenylsulfanyl-1,3-dihydro-indol-2-one 在 Me₄NF*4HF 作用下， 以 乙腈 为溶剂， 以64%的产率得到1-phenyl-3-fluoro-3-(phenylthio)oxindole
  参考文献：
  名称：

  Highly Regioselective Anodic Monofluorination of Oxindole and 3-Oxo-1,2,3,4-tetrahydroisoquinoline Derivatives

  摘要：

  使用Me4NF•4HF作为辅助电解质，成功对1-苯基-3-(苯硫基)吲哚(1a)、(1-(对甲苯基)-3-(苯硫基)-5-甲基吲哚(1b)进行了高度区域选择性单氟化反应，分别获得了64%和50%产率的相应3-氟化产物。同样，2-苄基-3-氧代-4-(苯硫基)-1,2,3,4-四氢异喹啉(1c)也通过Et4NF•3HF选择性氟化，获得了71%产率的4-氟化产物。

  DOI：

  10.1055/s-1997-3272
• 作为产物：
  描述：

  (苯基硫醇)乙酰氯 在 对甲苯磺酸 、 间氯过氧苯甲酸 作用下， 以 四氯化碳 为溶剂， 生成 1-Phenyl-3-phenylsulfanyl-1,3-dihydro-indol-2-one
  参考文献：
  名称：

  Electrolytic Partial Fluorination of Organic Compounds. 22.¹ Highly Regioselective Anodic Monofluorination of Oxindole and 3-Oxo-1,2,3,4-tetrahydroisoquinoline Derivatives: Effects of Supporting Fluoride Salts and Anode Materials

  摘要：

  Highly regioselective monofluorination of 1-aryl-3-(phenylthio)oxindoles and 2-substituted-3-oxo-4-(phenylthio)-1,2,3,4-tetrahydroisoquinolines can be successfully carried out in the presence of Me4NF . 4HF or Et4NF . 3HF as a supporting electrolyte to provide the corresponding S-fluorinated oxindole and 4-fluorinated isoquinoline derivatives in good yields. Carbon anodes as well as a platinum anode were found to be effective for the fluorination when Me4NF . 4HF was used as the supporting electrolyte.

  DOI：

  10.1021/jo971173i

文献信息

• Anodic Fluorination, Methoxylation, Acetoxylation, and Cyanation of Heteroatom Organic Compounds Using Boron‐Doped Diamond, GC, and Pt Electrodes
  作者：Hideyuki Nojima、Takashi Shimoda、Shinsuke Inagi、Toshio Fuchigami

  DOI：10.1002/ijch.202300025

  日期：——

  AbstractVarious anodic substitution reactions such as fluorination, methoxylation, acetoxylation, and cyanation of heteroatom compounds containing a sulfur or nitrogen atom were comparatively studied using boron‐doped diamond (BDD), Pt, and glassy carbon (GC) anodes. It was found that BDD anode is highly effective for these anodic substitution reactions similarly to Pt anode although both BDD and GC electrodes are carbon‐based materials.