N-(ethoxy(4-methoxyphenyl)methyl)benzamide | 137570-64-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(ethoxy(4-methoxyphenyl)methyl)benzamide
• 英文别名: N-[ethoxy-(4-methoxyphenyl)methyl]benzamide
• CAS: 137570-64-0
• 化学式: C₁₇H₁₉NO₃
• 分子量: 285.343
• InChiKey: FASOYPNDYBHWAM-UHFFFAOYSA-N

物化性质

• 沸点：
  479.9±45.0 °C(Predicted)
• 密度：
  1.120±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  苯硼酸酐 、 N-(ethoxy(4-methoxyphenyl)methyl)benzamide 在 2,2'-联吡啶 、 palladium diacetate 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 18.0h， 以83%的产率得到N-((4-methoxyphenyl)(phenyl)methyl)benzamide
  参考文献：
  名称：

  A palladium-catalyzed arylation of N-acyl-N,O-acetals with arylboronic reagents: synthesis of diarylmethylamines protected by easily removable acyl group

  摘要：

  An efficient process was developed to synthesis diarylmethylamines protected by a readily removable acyl group using a palladium-catalyzed arylation of N-acyl-N,O-acetals with arylboronic reagents. The attractive features of this protocol are: the ease of preparing substrate and the mild reaction condition under an air atmosphere. Moderate enantioselectivity was observed in preliminary screening studies of chiral ligands. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.06.017
• 作为产物：
  描述：

  乙醇 、 1-Benzotriazol-1-yl-N-benzoyl-1-(4-methoxyphenyl)-methylamine 在 sodium ethanolate 作用下， 以86%的产率得到N-(ethoxy(4-methoxyphenyl)methyl)benzamide
  参考文献：
  名称：

  N-[1-(Benzotriazol-1-yl)alkyl]amides, versatile amidoalkylation reagents. 5. A general and convenient route to N-(.alpha.-alkoxyalkyl)amides

  摘要：

  N-[1-(Benzotriazol-1-yl)alkyl]amides 2, easily prepared from benzotriazole 1, an aldehyde, and an amide, react readily with a variety of primary and secondary alcohols under mild conditions to give N-(alpha-alkoxyalkyl)amides 3 in good yield.

  DOI：

  10.1021/jo00028a028

文献信息

• Synthesis of <i>N</i>-Acyl-<i>N</i>,<i>O</i>-acetals Mediated by Titanium Ethoxide
  作者：Min Li、Bingling Luo、Qi Liu、Yumin Hu、A. Ganesan、Peng Huang、Shijun Wen

  DOI：10.1021/ol4031155

  日期：2014.1.3

  functional group can act as a synthetic precursor to unstable reactive N-acylimines. In this paper, a variety of N-acyl-O-ethyl-N,O-acetals was concisely prepared under mild conditions mediated by titanium ethoxide (Ti(OEt)4). The method also offers a new strategy to make other O-alkyl-N,O-acetals. Furthermore, this strategy was extended to the synthesis of an analogue of the natural product turtschamide

  N-酰基-N，O-缩醛存在于许多具有生物活性的天然产物中，并且这种不寻常的官能团可以充当不稳定的反应性N-酰基酰亚胺的合成前体。本文在乙醇钛（Ti（OEt）4）介导的温和条件下，简明地制备了各种N-酰基-O-乙基-N，O-缩醛。该方法还提供了制备其他O-烷基-N，O-乙缩醛的新策略。此外，该策略扩展到了天然产物turtschamide的类似物的合成。
• N-[1-(Benzotriazol-1-yl)alkyl]amides, versatile amidoalkylation reagents. 5. A general and convenient route to N-(.alpha.-alkoxyalkyl)amides
  作者：Alan R. Katritzky、Wei Qiang Fan、Michael Black、Juliusz Pernak

  DOI：10.1021/jo00028a028

  日期：1992.1

  N-[1-(Benzotriazol-1-yl)alkyl]amides 2, easily prepared from benzotriazole 1, an aldehyde, and an amide, react readily with a variety of primary and secondary alcohols under mild conditions to give N-(alpha-alkoxyalkyl)amides 3 in good yield.
• A palladium-catalyzed arylation of N-acyl-N,O-acetals with arylboronic reagents: synthesis of diarylmethylamines protected by easily removable acyl group
  作者：Qian Chen、Chao Liu、Fang Guo、Liang Li

  DOI：10.1016/j.tet.2015.06.017

  日期：2015.8

  An efficient process was developed to synthesis diarylmethylamines protected by a readily removable acyl group using a palladium-catalyzed arylation of N-acyl-N,O-acetals with arylboronic reagents. The attractive features of this protocol are: the ease of preparing substrate and the mild reaction condition under an air atmosphere. Moderate enantioselectivity was observed in preliminary screening studies of chiral ligands. (C) 2015 Elsevier Ltd. All rights reserved.