1-acetyl-2-phenyl-5-methoxyindole | 942924-10-9

• 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: 1-acetyl-2-phenyl-5-methoxyindole
• 英文别名: 1-(5-methoxy-2-phenyl-1H-indol-1-yl)ethan-1-one；1-(5-methoxy-2-phenyl-1H-indol-1-yl)ethanone；1-(5-Methoxy-2-phenylindol-1-yl)ethanone；1-(5-methoxy-2-phenylindol-1-yl)ethanone
• CAS: 942924-10-9
• 化学式: C₁₇H₁₅NO₂
• 分子量: 265.312
• InChiKey: OOPKYKAZFHMRLF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  31.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-methoxy-2-(phenylethynyl)aniline 在 吡啶 、 chlorocyclopentadienylbis(triphenylphosphine)ruthenium(II) 、 Sodium;tetrakis(2,3,4,5,6-pentafluorophenyl)boranuide;hydrate 作用下， 以 二氯甲烷 、 氯苯 为溶剂， 反应 12.0h， 生成 1-acetyl-2-phenyl-5-methoxyindole 、 1-(5-methoxy-3-phenyl-1H-indol-1-yl)ethan-1-one
  参考文献：
  名称：

  钌催化 2-炔基苯胺的环异构化：通过 1,2-碳迁移合成 3-取代吲哚

  摘要：

  我们开发了钌催化的炔基苯胺环异构化，以高产率得到 3-取代的吲哚。该反应通过由 1,2-碳迁移形成的二取代亚乙烯基钌配合物进行。

  DOI：

  10.1021/jacs.7b04564

文献信息

• Cu(II)-Catalyzed Direct and Site-Selective Arylation of Indoles Under Mild Conditions
  作者：Robert J. Phipps、Neil P. Grimster、Matthew J. Gaunt

  DOI：10.1021/ja801767s

  日期：2008.7.1

  We have developed a new site-selective Cu(II)-catalyzed C-H bond funtionalization process that can selectively arlate indoles at either the C3 or C2 position under miled conditions. The scope of arylation process is broad and tolerates broad functionality on both indole and aryl unit, which makes it amenable to further elaboartion. The mechanism of the arylation reaction is proposed to proceed via a Cu(III)-aryl that undergoes intial addition at the C3 position of the indole motif. We speculate that site of indole arylation arises through a migration of the Cu(III)-aryl group of C3 to C2, and this can be controlled by the nature of the group on the nitrogen atm; free (NH)-and N-alkylindoles deliver the C3-arylated product, whereas N-acytylindoles affored the C2 isomer, both with excellent yield and selectivity.
• Oxidant-controlled regioselectivity in the oxidative arylation of N-acetylindoles
  作者：Shathaverdhan Potavathri、Ashley S. Dumas、Timothy A. Dwight、Gregory R. Naumiec、Jeffrey M. Hammann、Brenton DeBoef

  DOI：10.1016/j.tetlet.2008.04.073

  日期：2008.6

  N-Acetylindoles can be oxidatively coupled with arenes such as benzene or pentafluorobenzene in dioxane. The use of Cu(OAc)(2) as the stoichiometric oxidant produces selective arylation at the 3-position of indole while AgOAc produces selective arylation at indole's 2-position. (C) 2008 Elsevier Ltd. All rights reserved.
• Ruthenium-Catalyzed Cycloisomerization of 2-Alkynylanilides: Synthesis of 3-Substituted Indoles by 1,2-Carbon Migration
  作者：Takuma Watanabe、Yuichiro Mutoh、Shinichi Saito

  DOI：10.1021/jacs.7b04564

  日期：2017.6.14

  We developed ruthenium-catalyzed cycloisomerization of alkynylanilides that gave 3-substituted indoles in high yields. The reaction proceeded via the disubstituted vinylidene ruthenium complex that was formed by the 1,2-carbon migration.

  我们开发了钌催化的炔基苯胺环异构化，以高产率得到 3-取代的吲哚。该反应通过由 1,2-碳迁移形成的二取代亚乙烯基钌配合物进行。