N-methyl-N-[(2,4,6-trimethoxyphenyl)methyl]acetamide | 1261063-38-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: N-methyl-N-[(2,4,6-trimethoxyphenyl)methyl]acetamide
• 英文别名: N-methyl-N-(2,4,6-trimethoxybenzyl)acetamide；2-(N-acetyl,N-methylamino)methyl-1,3,5-trimethoxybenzene
• CAS: 1261063-38-0
• 化学式: C₁₃H₁₉NO₄
• 分子量: 253.298
• InChiKey: NLDQPJSQHCKYAS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  48
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-methyl-N-[(2,4,6-trimethoxyphenyl)methyl]acetamide 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以78%的产率得到2-(N-ethyl,N-methylamino)methyl-1,3,5-trimethoxybenzene
  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：

  1,3,5-三甲氧基苯 、 N-(benzoyloxy)methyl,N-methylacetamide 反应 48.0h， 以67%的产率得到N-methyl-N-[(2,4,6-trimethoxyphenyl)methyl]acetamide
  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

文献信息

• Photocatalyst-Free, Visible-Light-Mediated C(sp³)–H Arylation of Amides via a Solvent-Caged EDA Complex
  作者：Jaspreet Kaur、Ahmed Shahin、Joshua P. Barham

  DOI：10.1021/acs.orglett.1c00132

  日期：2021.3.19

  A photocatalyst-free and mild visible light photochemical procedure for C(sp3)–H arylation of amides is described. The reaction proceeds via an electron donor–acceptor (EDA) complex between an electron-rich arene substrate and electron-poor persulfate oxidant. C(sp3)–H arylation of the amide occurs selectively with the most electron-rich arene of the substrate. Mechanistic studies corroborate the reaction

  描述了酰胺的C（sp 3）–H芳基化反应的无光催化剂和温和可见光光化学程序。反应通过富电子芳烃底物与贫电子过硫酸盐氧化剂之间的电子给体-受体（EDA）配合物进行。酰胺的C（sp 3）–H芳基化选择性地发生在底物最富电子的芳烃上。机理研究证实了该反应是在溶剂笼中进行的，溶剂笼中的组分紧密相邻。
• 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。
• Friedel–Crafts Amidoalkylation via Thermolysis and Oxidative Photocatalysis
  作者：Chunhui Dai、Francesco Meschini、Jagan M. R. Narayanam、Corey R. J. Stephenson

  DOI：10.1021/jo300162c

  日期：2012.5.4

  Friedel Crafts amidoalkylation was achieved by oxidation of dialkylamides using persulfate (S2O82-) in the presence of the visible light catalyst, Ru(bpy)(3)Cl-2, at room temperature, via a reactive N-acyliminium intermediate. Alternatively, mild heating of the dialkylamides and persulfate afforded a metal and Lewis acid-free Friedel-Crafts amidoalkylation. Alcohols and electron-rich arenes served as effective nucleophiles, forming new C-O or C-C bonds. In general, photocatalysis provided higher yields and better selectivities.
• 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.