1-methyl-2,3-bis<(4-methoxyphenyl)thio>indole | 158585-54-7

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 1-methyl-2,3-bis<(4-methoxyphenyl)thio>indole
• 英文别名: 2,3-bis((4-methoxyphenyl)thio)-1-methyl-1H-indole；2,3-Bis[(4-methoxyphenyl)sulfanyl]-1-methylindole
• CAS: 158585-54-7
• 化学式: C₂₃H₂₁NO₂S₂
• 分子量: 407.557
• InChiKey: FXDFFGJFMUASMX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  74
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-methyl-2,3-bis<(4-methoxyphenyl)thio>indole 在 硫代水杨酸 作用下， 以 三氟乙酸 为溶剂， 反应 0.25h， 以94%的产率得到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：

  4,4'-二甲氧基二苯二硫 在 磺酰氯 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.33h， 生成 1-methyl-2,3-bis<(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

文献信息

• 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。
• Copper-Catalyzed Multicomponent Reactions (MCRs) for Disulfenylation of Imidazo[1,2-<i>a</i>]pyridines Using Elemental Sulfur and Arylhalides and Intramolecular Cyclization of Haloimidazo[1,2-<i>a</i>]pyridines
  作者：Rashmi Semwal、Chitrakar Ravi、Soumya Saxena、Subbarayappa Adimurthy

  DOI：10.1021/acs.joc.9b01632

  日期：2019.11.1

  Copper-catalyzed synthesis of disulfenylated imidazo[1,2-a]pyridines and indoles using elemental sulfur and haloarenes through one-pot, three component reaction by two C-S-C bond formations has been developed. The method has a broad substrate scope with a variety of substituted haloarenes. The conditions were also applied for the synthesis of benzothieno-imidazo[1,2-a]pyridines in excellent yields

  已开发了通过单锅，两个CSC键形成的三组分反应，使用元素硫和卤代芳烃进行铜催化的二硫代咪唑并[1,2-a]吡啶和吲哚的合成。该方法具有广泛的底物范围，具有各种取代的卤代芳烃。该条件还适用于使用硫粉通过2-（2-卤代苯基）咪唑并[1,2-a]吡啶的分子内磺基磺化环化反应以优异的产率（99％）合成苯并噻吩并咪唑并[1,2-a]吡啶。
• 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.