5-Methyl-3-phenylsulfanyl-1-p-tolyl-1,3-dihydro-indol-2-one | 193815-37-1

• 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: 5-Methyl-3-phenylsulfanyl-1-p-tolyl-1,3-dihydro-indol-2-one
• 英文别名: 2H-Indol-2-one, 1,3-dihydro-5-methyl-1-(4-methylphenyl)-3-(phenylthio)-；5-methyl-1-(4-methylphenyl)-3-phenylsulfanyl-3H-indol-2-one
• CAS: 193815-37-1
• 化学式: C₂₂H₁₉NOS
• 分子量: 345.465
• InChiKey: CKIJAVJGGMTDNB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 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：

  5-Methyl-3-phenylsulfanyl-1-p-tolyl-1,3-dihydro-indol-2-one 在 Me₄NF*4HF 作用下， 以 乙腈 为溶剂， 以50%的产率得到3-Fluoro-5-methyl-3-phenylsulfanyl-1-p-tolyl-1,3-dihydro-indol-2-one
  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 5-Methyl-3-phenylsulfanyl-1-p-tolyl-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

• Highly Regioselective Anodic Monofluorination of Oxindole and 3-Oxo-1,2,3,4-tetrahydroisoquinoline Derivatives
  作者：Yankun Hou、Seiichiro Higashiya、Toshio Fuchigami

  DOI：10.1055/s-1997-3272

  日期：1997.6

  Highly regioselective monofluorination of 1-phenyl-3-(phenylthio)oxindole (1a), (1-(p-tolyl)-3-(phenylthio)-5-methyloxindole (1b) was successfully carried out using Me4NF•4HF as a supporting electrolyte to provide the corresponding 3-fluorinated products in 64% and 50% yields, respectively. Similarly, 2-benzyl-3-oxo-4-(phenylthio)-1,2,3,4-tetrahydroisoquinoline (1c) was also selectively fluorinated with Et4NF•3HF to give the 4-fluorinated product in 71% yield.

  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。
• 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
  作者：Yankun Hou、Seiichiro Higashiya、Toshio Fuchigami

  DOI：10.1021/jo971173i

  日期：1997.12.1

  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.