3-(tert-butylthio)-1-methyl-2-phenylindole | 148322-08-1

• 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: 3-(tert-butylthio)-1-methyl-2-phenylindole
• 英文别名: 3-Tert-butylsulfanyl-1-methyl-2-phenylindole
• CAS: 148322-08-1
• 化学式: C₁₉H₂₁NS
• 分子量: 295.448
• InChiKey: FHGBUGNCNRERTQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  30.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-(tert-butylthio)-1-methyl-2-phenylindole 在 硫代水杨酸 作用下， 以 三氟乙酸 为溶剂， 反应 1.5h， 以84%的产率得到1-甲基-2-苯基吲哚
  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：

  α-(tert-Butylthio)acetophenone 、 1-甲基-1-苯肼 在 sodium acetate 作用下， 以 溶剂黄146 为溶剂， 反应 3.0h， 以64%的产率得到3-(tert-butylthio)-1-methyl-2-phenylindole
  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

文献信息

• A general non-reductive method for the desulfenylation of 3-indolyl sulfides
  作者：Pierre Hamel、Nicolas Zajac、Joseph G. Atkinson、Yves Girard

  DOI：10.1016/s0040-4039(00)60345-3

  日期：1993.3

  In trifluoroacetic acid, in the presence of thiosalicylic acid as a trapping agent, 3-indolyl sulfides bearing a wide variety of substituents are smoothly and rapidly desulfenylated to the corresponding 3-unsubstituted indoles.
• 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：——