N-methyl-N-((1-methyl-1H-indol-3-yl)methyl)acetamide

• 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: N-methyl-N-((1-methyl-1H-indol-3-yl)methyl)acetamide
• 英文别名: N-methyl-N-[(1-methylindol-3-yl)methyl]acetamide
• 化学式: C₁₃H₁₆N₂O
• 分子量: 216.283
• InChiKey: OLWANRWWMUYDJA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  25.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-methyl-N-((1-methyl-1H-indol-3-yl)methyl)acetamide 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以88%的产率得到3-(N-ethyl,N-methylamino)methyl-1-methylindole
  参考文献：
  名称：

  用BPO和N，N-二甲基酰胺制备Hemiaminal衍生物的新方法及其在（氨甲基）吲哚中的合成用途

  摘要：

  通过在辐射或加热条件下BPO与N，N-二甲基酰胺的反应，可以以高收率获得Hemiaminal衍生物。通过使用血红素衍生物，可以通过弗瑞德-克来福特烷基化反应还原带有（N-酰基，N-甲基氨基）甲基的吲哚，从而平稳地获得带有（N-烷基，N-甲基氨基）甲基的吲哚。吲哚和半胱氨酸衍生物。

  DOI：

  10.1002/ejoc.202000680
• 作为产物：
  描述：

  1-甲基吲哚 、 N,N-二甲基乙酰胺 在 BF₄^(1-)*C₉H₂₁N*H⁽¹⁺⁾ 作用下， 以78%的产率得到N-methyl-N-((1-methyl-1H-indol-3-yl)methyl)acetamide
  参考文献：
  名称：

  使用准分裂电池和三烷基四氟硼酸铵的新型电化学氧化系统对芳烃进行电化学 Friedel-Crafts 型酰胺甲基化

  摘要：

  电化学Friedel-Crafts 型酰胺甲基化通过一种新型电化学氧化系统成功进行，该系统使用准分隔电池和四氟硼酸三烷基铵，例如iPr 2 NHEtBF 4。1,3,5-三甲氧基苯或吲哚在含有 0.1 M iPr 2 NHEtBF 4的 DMA 中使用配备有 Pt 板阴极和 Pt 线阳极的未分隔电池（准分隔电池）进行恒流电解，导致选择性形成N DMA的-酰基亚胺离子在阳极与芳烃反应以良好至高产率得到相应的酰胺甲基化产物。

  DOI：

  10.3762/bjoc.18.105

文献信息

• Direct C C coupling of indoles with alkylamides via oxidative C H functionalization using Fe3O(BDC)3 as a productive heterogeneous catalyst
  作者：Son H. Doan、Khoa D. Nguyen、Phuc T. Huynh、Tung T. Nguyen、Nam T.S. Phan

  DOI：10.1016/j.molcata.2016.07.042

  日期：2016.11

  used a recyclable heterogeneous catalyst for the direct C C coupling of indoles with alkylamides via oxidative C H functionalization. The catalyst expressed higher catalytic efficiency for the direct C C coupling transformation than that of other MOFs and that of other homogeneous iron catalysts. The coupling of indoles with alkylamides could only continued to form indole derivatives in the presence of

  摘要 制备了金属-有机骨架Fe 3 O(BDC) 3 ，并使用可回收的多相催化剂通过氧化CH官能化将吲哚与烷基酰胺直接CC偶联。与其他 MOF 和其他均相铁催化剂相比，该催化剂对直接 CC 偶联转化的催化效率更高。吲哚与烷基酰胺的偶联只能在固体骨架催化剂存在下继续形成吲哚衍生物，如果有的话，提供浸出的活性铁物质是微不足道的。Fe-MOF催化剂可以多次重复用于通过直接CC偶联合成吲哚衍生物，而不会显着降低催化活性。据我们所知，
• Iron-Catalyzed Oxidative Coupling of Alkylamides with Arenes through Oxidation of Alkylamides Followed by Friedel−Crafts Alkylation
  作者：Eiji Shirakawa、Nanase Uchiyama、Tamio Hayashi

  DOI：10.1021/jo102217m

  日期：2011.1.7

  FeCL(3) in combination with t-BuOOt-Bu as an oxidant was found to be an efficient catalyst for oxidation of alkylamides to alpha-(tert-butoxy)alkylamides. FeCl(2) and CuCl showed, respectively, almost the same and slightly lower activities compared with FeCl(3) in the tert-butoxylation of N-phenylpyrrolidone (1a), whereas no tert-butoxylated product was obtained by use of Fe(OTf)(3), RuCl(3), or Zr(OTf)(4). FeCl(3) was found to be effective also as a catalyst for the Friedel-Crafts alkylation with thus obtained alpha-(tert-butoxy)alkylamides. The Friedel-Crafts alkylation proceeded smoothly also in the presence of a catalytic amount of Fe(OTf)(3), RuCl(3), or Zr(OTf)(4). In contrast, FeCl(2) and CuCl, which showed certain activity toward the tert-butoxylation, failed to promote the Friedel Crafts alkylation. Among the transition metal complexes thus far examined, only FeCl(3) showed high catalytic activities for both the oxidation and the Friedel-Crafts alkylation. The bifunctionality of FeCl(3) was utilized for the oxidative coupling of alkylamides with arenes through a tandem reaction consisting of oxidation of alkylamides to alpha-(tert-butoxy)alkylamides and the following Friedel-Crafts alkylation. The FeCl(3)-catalyzed oxidative coupling is applicable to a wide variety of alkylamides and arenes, though a combination of FeCl(3) with Fe(OTf)(3) was found to be effective for the reaction of arenes with low nucleophilicity. A Fe(II)-Fe(III) catalytic cycle is concerned with the tert-butoxylation, whereas a Fe(III) complex as a Lewis acid catalyzes the Friedel-Crafts alkylation.
• Ikeda, Kiyoshi; Morimoto, Toshiaki; Sekiya, Minoru, Chemical and pharmaceutical bulletin, 1980, vol. 28, # 4, p. 1178 - 1182
  作者：Ikeda, Kiyoshi、Morimoto, Toshiaki、Sekiya, Minoru

  DOI：——

  日期：——
• Novel Preparation of Hemiaminal Derivatives with BPO and <i>N,N</i> -Dimethylamides and Their Synthetic Use for (Aminomethyl)indoles
  作者：Kohei Nakamura、Hideo Togo

  DOI：10.1002/ejoc.202000680

  日期：2020.8.16

  N‐dimethylamides under irradiation or warming condition. By using the hemiaminal derivatives, indoles bearing a (N‐alkyl,N‐methylamino)methyl group could be smoothly obtained by the reduction of the indoles bearing a (N‐acyl,N‐methylamino)methyl group through the Friedel–Crafts alkylation reaction of indoles and the hemiaminal derivatives.

  通过在辐射或加热条件下BPO与N，N-二甲基酰胺的反应，可以以高收率获得Hemiaminal衍生物。通过使用血红素衍生物，可以通过弗瑞德-克来福特烷基化反应还原带有（N-酰基，N-甲基氨基）甲基的吲哚，从而平稳地获得带有（N-烷基，N-甲基氨基）甲基的吲哚。吲哚和半胱氨酸衍生物。
• Electrochemical Friedel–Crafts-type amidomethylation of arenes by a novel electrochemical oxidation system using a quasi-divided cell and trialkylammonium tetrafluoroborate
  作者：Hisanori Senboku、Mizuki Hayama、Hidetoshi Matsuno

  DOI：10.3762/bjoc.18.105

  日期：——

  Electrochemical Friedel–Crafts-type amidomethylation was successfully carried out by a novel electrochemical oxidation system using a quasi-divided cell and trialkylammonium tetrafluoroborates, such as iPr2NHEtBF4. Constant current electrolysis of 1,3,5-trimethoxybenzene or indoles in DMA containing 0.1 M iPr2NHEtBF4 using an undivided cell equipped with a Pt plate cathode and a Pt wire anode (a quasi-divided

  电化学Friedel-Crafts 型酰胺甲基化通过一种新型电化学氧化系统成功进行，该系统使用准分隔电池和四氟硼酸三烷基铵，例如iPr 2 NHEtBF 4。1,3,5-三甲氧基苯或吲哚在含有 0.1 M iPr 2 NHEtBF 4的 DMA 中使用配备有 Pt 板阴极和 Pt 线阳极的未分隔电池（准分隔电池）进行恒流电解，导致选择性形成N DMA的-酰基亚胺离子在阳极与芳烃反应以良好至高产率得到相应的酰胺甲基化产物。