6-methoxy-3-(phenylthio)-1H-indole | 92552-56-2

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 6-methoxy-3-(phenylthio)-1H-indole
• 英文别名: <6-Methoxy-indolyl-(3)>-thiophenylaether；6-methoxy-3-phenylsulfanyl-indole；6-methoxy-3-phenylsulfanyl-1H-indole
• CAS: 92552-56-2
• 化学式: C₁₅H₁₃NOS
• 分子量: 255.34
• InChiKey: PVNKSTSUPSYMNK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  50.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-methoxy-3-(phenylthio)-1H-indole 在 Oxone 、 碳酸氢钠 作用下， 以 丙酮 为溶剂， 生成 3-(benzenesulfonyl)-6-methoxy-1H-indole
  参考文献：
  名称：

  1-(2-Aminoethyl)-3-(arylsulfonyl)-1H-indoles as novel 5-HT6 receptor ligands

  摘要：

  Novel 1-(2-aminoethyl)-3-(arylsulfonyl)-1H-indoles were prepared. Binding assays indicated they are 5-HT6 receptor ligands, among which N,N-dimethyl-N-{2-[3-(1-naphthylsulfonyl)-1H-indol-1-yl]ethyl}amine 8t and N-methyl-N-{2-[3-(1-naphthylsulfonyl)-1H-indol-1-yl]ethyl}amine 8u showed high affinity for 5-HT6 receptors with K-i = 3.7 and 5.7nM, respectively. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.09.003
• 作为产物：
  描述：

  6-甲氧基吲哚 、 N-(苯硫基)邻苯二甲酰亚胺 在 cerium(III) chloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以87%的产率得到6-methoxy-3-(phenylthio)-1H-indole
  参考文献：
  名称：

  The use of anhydrous CeCl3 as a catalyst for the synthesis of 3-sulfenyl indoles

  摘要：

  Anhydrous CeCl3 was successfully used as a catalyst for the synthesis of several 3-sulfenyl indoles in good to excellent yields through the reaction of indole with N-(alkylthio) and N-(arylthio)phthalimides in DMF. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.02.038

文献信息

• Palladium-Catalyzed Oxidative Sulfenylation of Indoles and Related Electron-Rich Heteroarenes with Aryl Boronic Acids and Elemental Sulfur
  作者：Jianxiao Li、Chunsheng Li、Shaorong Yang、Yanni An、Wanqing Wu、Huanfeng Jiang

  DOI：10.1021/acs.joc.6b01428

  日期：2016.9.2

  An efficient and convenient palladium-catalyzed C–H bond oxidative sulfenylation of indoles and related electron-rich heteroarenes with aryl boronic acids and elemental sulfur has been described. This procedure provides a useful and direct approach for the assembly of a wide range of structurally diverse 3-sulfenylheteroarenes with moderate to excellent yields from simple and readily available starting

  已经描述了一种有效且方便的钯催化的吲哚和相关的富电子杂芳烃与芳基硼酸和元素硫的C-H键氧化亚磺酰化反应。该方法提供了一种有用且直接的方法，用于从简单易得的起始原料中以中等至极好的收率组装各种结构多样的3-亚硫基杂芳烃。此外，该合成方案适用于N-保护的和未保护的吲哚。值得注意的是，这一转换也一步完成了两个C–S键的构建。
• 1-(2-Aminoethyl)-3-(arylsulfonyl)-1H-indoles as novel 5-HT6 receptor ligands
  作者：Ronald Bernotas、Steven Lenicek、Schuyler Antane、Guo Ming Zhang、Deborah Smith、Joseph Coupet、Boyd Harrison、Lee E. Schechter

  DOI：10.1016/j.bmcl.2004.09.003

  日期：2004.11

  Novel 1-(2-aminoethyl)-3-(arylsulfonyl)-1H-indoles were prepared. Binding assays indicated they are 5-HT6 receptor ligands, among which N,N-dimethyl-N-2-[3-(1-naphthylsulfonyl)-1H-indol-1-yl]ethyl}amine 8t and N-methyl-N-2-[3-(1-naphthylsulfonyl)-1H-indol-1-yl]ethyl}amine 8u showed high affinity for 5-HT6 receptors with K-i = 3.7 and 5.7nM, respectively. (C) 2004 Elsevier Ltd. All rights reserved.
• The use of anhydrous CeCl3 as a catalyst for the synthesis of 3-sulfenyl indoles
  作者：Claudio C. Silveira、Samuel R. Mendes、Lucas Wolf、Guilherme M. Martins

  DOI：10.1016/j.tetlet.2010.02.038

  日期：2010.4

  Anhydrous CeCl3 was successfully used as a catalyst for the synthesis of several 3-sulfenyl indoles in good to excellent yields through the reaction of indole with N-(alkylthio) and N-(arylthio)phthalimides in DMF. (C) 2010 Elsevier Ltd. All rights reserved.