5-bromo-2-methyl-3-(phenylthio)-1H-indole

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 5-bromo-2-methyl-3-(phenylthio)-1H-indole
• 英文别名: 5-bromo-2-methyl-3-(phenylthio)indole；5-bromo-2-methyl-3-phenylsulfanyl-1H-indole
• 化学式: C₁₅H₁₂BrNS
• 分子量: 318.237
• InChiKey: HZHJEYSVYMIXJU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  41.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5-bromo-2-methyl-3-(phenylthio)-1H-indole 在 硫代水杨酸 作用下， 以 三氟乙酸 为溶剂， 反应 0.5h， 以91%的产率得到5-溴-2-甲基吲哚
  参考文献：
  名称：

  Nonreductive Desulfenylation of 3-Indolyl Sulfides. Improved Syntheses of 2-Substituted Indoles and 2-Indolyl Sulfides

  摘要：

  Desulfenylation of 3-indolyl sulfides to the corresponding 3-unsubstituted indoles is usually carried out under reductive conditions, thus accommodating only substituents which are resistant to reduction. We have developed a nonreductive procedure for removal of a sulfide at the 3-position of indoles, using trifluoroacetic acid in the presence of a thiol as trapping agent, which is compatible with a large array of functionalities on the indole ring. In addition, the desulfenylation occurs selectively at the 3-position of the indole, and sulfide groups at other positions of the molecule remain untouched. Thus, indole 2,3-bis-sulfides are selectively desulfenylated at the 3-position, affording 3-unsubstituted 2-indolyl sulfides. This methodology broadens the use of sulfide as a protecting group for the 3-position of indoles.

  DOI：

  10.1021/jo00100a045
• 作为产物：
  描述：

  3-(tert-butylthio)-1-methyl-2-phenylindole 以47%的产率得到
  参考文献：
  名称：

  Hamel Pierre, Zajac Nicolas, Atkinson Joseph G., Girard Yves, J. Org. Chem, 59 (1994) N 21, S 6372-6377

  摘要：

  DOI：

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。
• Hamel Pierre, Zajac Nicolas, Atkinson Joseph G., Girard Yves, J. Org. Chem, 59 (1994) N 21, S 6372-6377
  作者：Hamel Pierre, Zajac Nicolas, Atkinson Joseph G., Girard Yves

  DOI：——

  日期：——
• Nonreductive Desulfenylation of 3-Indolyl Sulfides. Improved Syntheses of 2-Substituted Indoles and 2-Indolyl Sulfides
  作者：Pierre Hamel、Nicolas Zajac、Joseph G. Atkinson、Yves Girard

  DOI：10.1021/jo00100a045

  日期：1994.10

  Desulfenylation of 3-indolyl sulfides to the corresponding 3-unsubstituted indoles is usually carried out under reductive conditions, thus accommodating only substituents which are resistant to reduction. We have developed a nonreductive procedure for removal of a sulfide at the 3-position of indoles, using trifluoroacetic acid in the presence of a thiol as trapping agent, which is compatible with a large array of functionalities on the indole ring. In addition, the desulfenylation occurs selectively at the 3-position of the indole, and sulfide groups at other positions of the molecule remain untouched. Thus, indole 2,3-bis-sulfides are selectively desulfenylated at the 3-position, affording 3-unsubstituted 2-indolyl sulfides. This methodology broadens the use of sulfide as a protecting group for the 3-position of indoles.