2,4-bis(N-acetyl-N-methylaminomethyl)-1,3,5-trimethoxybenzene | 1261063-49-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2,4-bis(N-acetyl-N-methylaminomethyl)-1,3,5-trimethoxybenzene
• 英文别名: N-[[3-[[acetyl(methyl)amino]methyl]-2,4,6-trimethoxyphenyl]methyl]-N-methylacetamide
• CAS: 1261063-49-3
• 化学式: C₁₇H₂₆N₂O₅
• 分子量: 338.404
• InChiKey: XJTAFUSSJHQKKR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  68.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1,3,5-三甲氧基苯 、 N,N-二甲基乙酰胺 在 BF₄^(1-)*C₉H₂₁N*H⁽¹⁺⁾ 作用下， 以71%的产率得到N-methyl-N-[(2,4,6-trimethoxyphenyl)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

• 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.