3-(2,5-diphenylthiophen-3-yl)-1H-indole | 1198214-20-8

• 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-(2,5-diphenylthiophen-3-yl)-1H-indole
• CAS: 1198214-20-8
• 化学式: C₂₄H₁₇NS
• 分子量: 351.472
• InChiKey: KGFMJMLZXQYFOA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  44
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-(1H-indol-3-yl)-1,4-diphenylbutane-1,4-dione 在 劳森试剂 作用下， 以 甲苯 为溶剂， 反应 0.5h， 以79%的产率得到3-(2,5-diphenylthiophen-3-yl)-1H-indole
  参考文献：
  名称：

  Indirect regioselective heteroarylation of indoles through a Friedel–Crafts reaction with (E)-1,4-diaryl-2-buten-1,4-diones

  摘要：

  A two-step synthesis of 3-heteroaryl indoles has been developed. The first step of the sequence involves a Friedel-Crafts alkylation of indoles with 1,4-diaryl-2-buten-1,4-diones to give the corresponding indoles bearing a 1,4-dicarbonyl moiety. The reaction is catalyzed by InCl3 and takes place with good yields. Cyclization of the diones under different Paal-Knorr conditions allows to prepare indoles substituted at the C3 position with 3-furanyl, 3-pyrrolyl- and 3-thienyl moieties. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.09.011

文献信息

• Indirect regioselective heteroarylation of indoles through a Friedel–Crafts reaction with (E)-1,4-diaryl-2-buten-1,4-diones
  作者：Gonzalo Blay、Isabel Fernández、Alicia Monleón、José R. Pedro、Carlos Vila

  DOI：10.1016/j.tet.2009.09.011

  日期：2009.11

  A two-step synthesis of 3-heteroaryl indoles has been developed. The first step of the sequence involves a Friedel-Crafts alkylation of indoles with 1,4-diaryl-2-buten-1,4-diones to give the corresponding indoles bearing a 1,4-dicarbonyl moiety. The reaction is catalyzed by InCl3 and takes place with good yields. Cyclization of the diones under different Paal-Knorr conditions allows to prepare indoles substituted at the C3 position with 3-furanyl, 3-pyrrolyl- and 3-thienyl moieties. (c) 2009 Elsevier Ltd. All rights reserved.