2,3-bis<(4-methoxyphenyl)thio>indole | 158585-52-5

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2,3-bis<(4-methoxyphenyl)thio>indole
• 英文别名: 2,3-bis((4-methoxyphenyl)thio)-1H-indole；2,3-bis[(4-methoxyphenyl)thio]-1H-indole；2,3-bis[(4-methoxyphenyl)sulfanyl]-1H-indole
• CAS: 158585-52-5
• 化学式: C₂₂H₁₉NO₂S₂
• 分子量: 393.53
• InChiKey: QUQMTUMNVVHRRV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  84.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,3-bis<(4-methoxyphenyl)thio>indole 在 硫代水杨酸 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 三氟乙酸 为溶剂， 反应 0.25h， 生成 1-methyl-2-<(4-methoxyphenyl)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
• 作为产物：
  描述：

  4-甲氧基苯硫酚 在 叔丁基过氧化氢 、 ammonium peroxydisulfate 、 碘 作用下， 以 甲醇 为溶剂， 生成 2,3-bis<(4-methoxyphenyl)thio>indole
  参考文献：
  名称：

  吲哚的金属游离亚磺酰基和双亚磺酰基：过硫酸盐介导的合成†

  摘要：

  提出了一种避免金属和卤素的方法，该方法使用过硫酸铵在甲醇中由吲哚和二芳基二硫化物合成3-芳基硫代吲哚。此外，使用碘和过硫酸铵还可以实现吲哚在2位和3位的双C–H亚磺酰基化。

  DOI：

  10.1039/c3ob41601a

文献信息

• Iodine-Catalyzed Mono- and Disulfenylation of Indoles in PEG₄₀₀ through a Facile Microwave-Assisted Process
  作者：Rajjakfur Rahaman、Pranjit Barman

  DOI：10.1002/ejoc.201701293

  日期：2017.11.16

  An iodine-catalyzed versatile green method for the synthesis of mono- and 2,3-bis-sulfenyl indoles has been presented. Various indoles can react with alkyl or aryl sodium sulfinates using hydrogen peroxide as an oxidizing agent in PEG400 under microwave conditions. This simple method enabled the rapid synthesis of mono- and 2,3-bis-sulfenylindoles with good to excellent yields under metal free conditions

  提出了一种用于合成单-和 2,3-双-亚磺基吲哚的碘催化多功能绿色方法。在微波条件下，使用过氧化氢作为氧化剂在 PEG400 中，各种吲哚可以与烷基或芳基亚磺酸钠反应。这种简单的方法能够在无金属条件下快速合成单-和 2,3-双-亚磺基吲哚，收率良好至极好。该协议的显着特点包括环境友好、无味、反应时间短、操作简便、反应条件温和、官能团耐受性好。
• Cu-Catalysed Direct Bis-Thiolation of Benzoheterocycles with Arylsulfonyl Hydrazides
  作者：Lingjuan Chen、Jiangxin Pu、Ping Liu、Bin Dai

  DOI：10.3184/174751918x15350179602459

  日期：2018.9

  bis-arylsulfenylated indoles (10), benzofurans (3), and benzothiophenes (3) and of monosulfenylated indoles (5), 12 of which are novel, were prepared in good yields via a Cu-catalysed direct sulfenylation of benzoheterocycles with arylsulfonyl hydrazides. Sulfonothioates are probably the major thiolated intermediates in this transformation.

  通过铜催化苯并杂环的直接磺基化，以良好的收率制备了一系列双芳基磺基化吲哚 (10)、苯并呋喃 (3) 和苯并噻吩 (3) 以及单磺基化吲哚 (5)，其中 12 个是新型的芳基磺酰肼。硫代磺酸盐可能是该转化中主要的硫醇化中间体。
• 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：——
• Metal free sulfenylation and bis-sulfenylation of indoles: persulfate mediated synthesis
  作者：Ch. Durga Prasad、Shailesh Kumar、Moh. Sattar、Amit Adhikary、Sangit Kumar

  DOI：10.1039/c3ob41601a

  日期：——

  A method which avoids metal and halogen for the synthesis of 3-arylthioindoles from indoles and diaryl disulfides using ammonium persulfate in methanol has been presented. Moreover, double C–H sulfenylation of indoles at 2 and 3-positions has also been achieved using iodine and ammonium persulfate.

  提出了一种避免金属和卤素的方法，该方法使用过硫酸铵在甲醇中由吲哚和二芳基二硫化物合成3-芳基硫代吲哚。此外，使用碘和过硫酸铵还可以实现吲哚在2位和3位的双C–H亚磺酰基化。
• 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.