2,5-dimethyl-3-(phenylthio)-1H-indole | 64137-76-4

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2,5-dimethyl-3-(phenylthio)-1H-indole
• 英文别名: 2,5-dimethyl-3-phenylthioindole；2,5-dimethyl-3-phenylsulfanyl-indole；<2,5-Dimethyl-indolyl-(3)>-thiophenylaether；<2,5-Dimethyl-indolyl-(3)>-thiophenylether；2,5-dimethyl-3-phenylsulfanyl-1H-indole
• CAS: 64137-76-4
• 化学式: C₁₆H₁₅NS
• 分子量: 253.368
• InChiKey: ZBTSSMKVHPWANU-UHFFFAOYSA-N

物化性质

• 沸点：
  416.8±40.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  41.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  4-(Benzenesulfinyl)-2,3,5,6-tetramethylphenol 在 三氟甲磺酸三甲基硅酯 、 对甲苯磺酸 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 1.17h， 生成 2,5-dimethyl-3-(phenylthio)-1H-indole
  参考文献：
  名称：

  Facile and Efficient Sulfenylation Method Using Quinone Mono-O,S-Acetals under Mild Conditions

  摘要：

  A novel sulfenylation method induced by aromatization of quinone mono-O,S-acetals is described. These sulfenylation reagents readily react with silyl enolethers or electron rich aromatic compounds to give sulfenylation products under mild conditions. In particular, O,S-acetal 2j, which possesses a pentafluorophenylthio function, is the most effective reagent from the standpoint of the adaptability for various substrates.

  DOI：

  10.1021/jo001710q

文献信息

• Visible-light promoted synthesis of 3-arylthioindoles from indoles and diaryl disulfides
  作者：Lin-miao Ye、Jie Chen、Peng Mao、Xue-jing Zhang、Ming Yan

  DOI：10.1016/j.tetlet.2017.05.090

  日期：2017.7

  3-Arylthioindoles could be synthesized in good yields via the photoirradiation of indoles and disulfides. The reaction is efficiently promoted by the catalytic amount of sodium iodide. A reaction mechanism involving the electrophilic substitution of indoles with arylsulfenyl iodine intermediates is suggested.

  可以通过吲哚和二硫化物的光辐射以高收率合成3-芳硫基吲哚。催化量的碘化钠可有效地促进反应。提出了涉及用芳基亚硫基碘中间体亲电取代吲哚的反应机理。
• Facile and Efficient Sulfenylation Method Using Quinone Mono-<i>O,S</i>-Acetals under Mild Conditions
  作者：Masato Matsugi、Kenji Murata、Kentoku Gotanda、Hisanori Nambu、Gopinathan Anilkumar、Keita Matsumoto、Yasuyuki Kita

  DOI：10.1021/jo001710q

  日期：2001.4.1

  A novel sulfenylation method induced by aromatization of quinone mono-O,S-acetals is described. These sulfenylation reagents readily react with silyl enolethers or electron rich aromatic compounds to give sulfenylation products under mild conditions. In particular, O,S-acetal 2j, which possesses a pentafluorophenylthio function, is the most effective reagent from the standpoint of the adaptability for various substrates.