5-(2-甲氧基苯基)吲哚 | 144104-45-0

• 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
• 中文名称: 5-(2-甲氧基苯基)吲哚
• 英文名称: 5-(2-methoxyphenyl)indole
• 英文别名: 5-(2-methoxyphenyl)-1H-indole
• CAS: 144104-45-0
• 化学式: C₁₅H₁₃NO
• 分子量: 223.274
• InChiKey: KRAVCWUHRVGOGK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  25
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5-(2-甲氧基苯基)吲哚 在 dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer 、 sodium acetate 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 28.0h， 生成 2-(2,2-difluorovinyl)-N-ethoxy-5-(2-methoxyphenyl)-1H-indole-1-carboxamide
  参考文献：
  名称：

  Cp * Rh（III）-α，α-二氟乙烯基甲苯磺酸酯催化吲哚的CH键二氟乙烯基化。

  摘要：

  前所未有的Rh（III）催化的吲哚CH-H键二氟乙烯基化已经成功开发，这种方法提供了一个通过C-H键激活直接二氟乙烯基化反应的例子，鲜有报道。在这种情况下，N-乙氧基氨基甲酰基用作导向基团，并且2，2-二氟乙烯基甲苯磺酸酯用于构建二氟乙烯基取代的吲哚。该方法提供了中等至良好产率的吲哚二氟乙烯基化的实用策略，并且其特征在于广泛的合成用途，温和的条件和高效率。

  DOI：

  10.1021/acs.joc.9b00957
• 作为产物：
  描述：

  5-溴吲哚 在 四(三苯基膦)钯 、 potassium hydride 、 sodium carbonate 作用下， 以 四氢呋喃 、 乙醇 、 甲苯 为溶剂， 反应 5.42h， 生成 5-(2-甲氧基苯基)吲哚
  参考文献：
  名称：

  Arylboronic Acids and Arylpinacolboronate Esters in Suzuki Coupling Reactions Involving Indoles. Partner Role Swapping and Heterocycle Protection

  摘要：

  Yields of Suzuki couplings involving indoles depended upon (i) whether arylboronic acids or arylpinacolboronate esters were used, (ii) whether the heterocycle was the aryl halide or the arylboron coupling partner, and (iii) whether the heterocycle was protected or not. Highest yields, which were unaffected by incorporating Boc or Tos protection at the heterocyclic nitrogen, were obtained when indole bromides were reacted with phenylboronic acids. When indolylboronic acids were reacted with phenyl bromides, yields were somewhat lower and depended on the nitrogen substituent, being highest in the absence of protection, lower in the presence of the Boc group, and lowest of all with the Tos group. Arylpinacolboronate esters were less reactive than arylboronic acids. They required considerably longer reaction times and furnished generally lower yields of biaryl. Furthermore, irrespective of whether the heterocycle was the aryl bromide or the arylpinacolboronate ester, these yields were highest when it was protected with the Tos group. Yields were lower with the Boc group, and unprotected heterocycles gave only traces of biaryl. Careful selection of arylboron reagent, of coupling partner roles, and of protecting groups are essential to ensuring optimum results in these Suzuki couplings. These results may also be relevant to couplings involving other substrates.

  DOI：

  10.1021/jo0491612

文献信息

• Novel modulators of potassium channels
  申请人：4SC AG

  公开号：US20030203959A1

  公开（公告）日：2003-10-30

  The invention relates to the use of a compound of the Formula (I) 1 or a salt, a physiologically functional derivative, or a prodrug thereof as a medicament, wherein R is a monocyclic or polycyclic substituted or unsubstituted aromatic ring system which may contain one or more groups X and which contains at least one aromatic ring; X is selected from the group consisting of S, O, N, NR′, SO or SO 2 ; R is optionally substituted by one to four substituents which are independently selected from the group consisting of halogen, CF 3 , OCF 3 , alkyl, cycloalkyl, haloalkyl, haloalkyloxy, hydroxyalkyl, hydroxyalkylamine, amine, aminoalkyl, alkylamine, CR′O, CO 2 R′, alkoxy, alkylthio, alkylaryl, alkylsulfonyl, H, hydroxy, aryl, heteroaryl, —NR′OR′, CN, alkylsulfinyl, arylsulfonyl, heteroarylsulfonyl, SO 3 R′, NO 2 , —CO—NR′R 1 , arylalkyl-O—, —O-aryl, —O-heteroaryl, arylalkyl-S—, —S-aryl, —S-heteroaryl, —NR 1 —SO 2 R′, —SO 2 —NR I -alkyl, —SO 2 —NR 1 -aryl, and —SO 2 —N 1 -heteroaryl.

  本发明涉及式（I）化合物的用途 1 或其盐、生理功能衍生物或其原药作为药物，其中 R 是单环或多环取代或未取代的芳香环系统，可包含一个或多个基团 X，且至少包含一个芳香环； X 选自 S、O、N、NR′、SO 或 SO 2 ; R 可任选被一至四个取代基取代，这些取代基独立地选自由卤素、CF 3 、OCF 3 烷基、环烷基、卤代烷基、卤代烷氧基、羟基烷基、羟基烷基胺、胺、氨基烷基、烷基胺、CR′O、CO 2 R′、烷氧基、烷硫基、烷芳基、烷基磺酰基、H、羟基、芳基、杂芳基、-NR′OR′、CN、烷基亚磺酰基、芳基磺酰基、杂芳基磺酰基、SO 3 R′、NO 2 、-CO-NR′R 1 ，芳烷基-O-，-O-芳基，-O-杂芳基，芳烷基-S-，-S-芳基，-S-杂芳基，-NR 1 -SO 2 R′、-SO 2 -NR I -烷基、-SO 2 -NR 1 -芳基和 -SO 2 -N 1 -杂芳基。
• Yang, Youhua; Martin, Arnold R., Heterocycles, 1992, vol. 34, # 7, p. 1395 - 1398
  作者：Yang, Youhua、Martin, Arnold R.

  DOI：——

  日期：——
• Arylboronic Acids and Arylpinacolboronate Esters in Suzuki Coupling Reactions Involving Indoles. Partner Role Swapping and Heterocycle Protection
  作者：Mònica Prieto、Esther Zurita、Esmeralda Rosa、Lourdes Muñoz、Paul Lloyd-Williams、Ernest Giralt

  DOI：10.1021/jo0491612

  日期：2004.10.1

  Yields of Suzuki couplings involving indoles depended upon (i) whether arylboronic acids or arylpinacolboronate esters were used, (ii) whether the heterocycle was the aryl halide or the arylboron coupling partner, and (iii) whether the heterocycle was protected or not. Highest yields, which were unaffected by incorporating Boc or Tos protection at the heterocyclic nitrogen, were obtained when indole bromides were reacted with phenylboronic acids. When indolylboronic acids were reacted with phenyl bromides, yields were somewhat lower and depended on the nitrogen substituent, being highest in the absence of protection, lower in the presence of the Boc group, and lowest of all with the Tos group. Arylpinacolboronate esters were less reactive than arylboronic acids. They required considerably longer reaction times and furnished generally lower yields of biaryl. Furthermore, irrespective of whether the heterocycle was the aryl bromide or the arylpinacolboronate ester, these yields were highest when it was protected with the Tos group. Yields were lower with the Boc group, and unprotected heterocycles gave only traces of biaryl. Careful selection of arylboron reagent, of coupling partner roles, and of protecting groups are essential to ensuring optimum results in these Suzuki couplings. These results may also be relevant to couplings involving other substrates.
• Cp*Rh(III)-Catalyzed C–H Bond Difluorovinylation of Indoles with α,α-Difluorovinyl Tosylate
  作者：Lisheng Yang、Chunpu Li、Dechuan Wang、Hong Liu

  DOI：10.1021/acs.joc.9b00957

  日期：2019.6.7

  Unprecedented Rh(III)-catalyzed C–H bond difluorovinylation of indoles has been successfully developed, and this method provided an example of direct difluorovinylation reaction through C–H bond activation which was rarely reported. In this context, N-ethoxycarbamoyl served as the directing group and 2,2-difluorovinyl tosylates were used for the construction of difluorovinyl-substituted indoles. This

  前所未有的Rh（III）催化的吲哚CH-H键二氟乙烯基化已经成功开发，这种方法提供了一个通过C-H键激活直接二氟乙烯基化反应的例子，鲜有报道。在这种情况下，N-乙氧基氨基甲酰基用作导向基团，并且2，2-二氟乙烯基甲苯磺酸酯用于构建二氟乙烯基取代的吲哚。该方法提供了中等至良好产率的吲哚二氟乙烯基化的实用策略，并且其特征在于广泛的合成用途，温和的条件和高效率。