2-<(2-naphthyl)thio>indole | 130128-87-9

• 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-<(2-naphthyl)thio>indole
• 英文别名: 2-(naphthalen-2-ylsulfanyl)-1H-indole；2-(2-naphthylthio)indole；2-(2-naphthylthio)-1H-indole；2-naphthalen-2-ylsulfanyl-1H-indole
• CAS: 130128-87-9
• 化学式: C₁₈H₁₃NS
• 分子量: 275.374
• InChiKey: MRLBMJHIYOFSIZ-UHFFFAOYSA-N

物化性质

• 熔点：
  117-119 °C
• 沸点：
  513.5±23.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  2,3-bis(2-naphthylthio)indole 在 硫代水杨酸 作用下， 以 三氟乙酸 为溶剂， 反应 1.0h， 以90%的产率得到2-<(2-naphthyl)thio>indole
  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

• TFA-promoted direct C–H sulfenylation at the C2 position of non-protected indoles
  作者：Thomas Hostier、Vincent Ferey、Gino Ricci、Domingo Gomez Pardo、Janine Cossy

  DOI：10.1039/c5cc05421d

  日期：——

  An efficient metal-free C–H sulfenylation process at the C2 position of non-protected indoles has been developed.

  一种高效的无金属C-H砜基化过程已经在非保护吲哚的C2位置上开发出来。
• Unexpected acid-catalysed rearrangement of certain 3-(arylthio)indoles to 2-(2-aminophenyl)benzothiophenes
  作者：Pierre Hamel、Yves Girard、Joseph G. Atkinson、Michael A. Bernstein

  DOI：10.1039/c39900001072

  日期：——

  3-(Arylthio)indoles (1), in which the aryl group is an electron-rich ring system, undergo a novel structural rearrangement to 2-(2-aminophenyl)benzothiophenes (2) upon heating in polyphosphoric acid.

  3-（芳硫基）吲哚（1），其中的芳基是一个富电子环系统，在多磷酸中加热后会发生新的结构重排，生成2-（2-氨基苯基）苯并噻吩（2）。
• Acid-catalyzed isomerization of 3-indolyl sulfides to 2-indolyl sulfides: first synthesis of 3-unsubstituted 2-arylthioindoles. Evidence for a complex intermolecular process
  作者：Pierre Hamel、Yves Girard、Joseph G. Atkinson

  DOI：10.1021/jo00035a029

  日期：1992.4

  The acid-catalyzed isomerization of 3-indolyl sulfides 1 to the corresponding 2-indolyl sulfides 4 provides the first synthesis of 3-unsubstituted 2-(arylthio)indoles, a hitherto unattainable class of compounds. When catalyzed by trifluoroacetic acid, the isomerization proceeds mainly via an intermolecular mechanism involving initial disproportionation to a 2,3-indolyl bis-sulfide 5 and an unsubstituted counterpart 6 followed by further interaction of these species to yield the rearranged isomer 4. A mechanism is proposed involving a role for the acid in the sulfenyl-transfer steps. This type of process also occurs, to a lesser extent, in the polyphosphoric acid catalyzed isomerization.
• HAMEL, PIERRE;GIRARD, YVES;ATKINSON, JOSEPH G.;BERNSTEIN, MICHAEL A., J. CHEM. SOC. CHEM. COMMUN.,(1990) N6, C. 1072-1074
  作者：HAMEL, PIERRE、GIRARD, YVES、ATKINSON, JOSEPH G.、BERNSTEIN, MICHAEL A.

  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.