3-methoxy-N-(3-phenylpropyl)-benzamide

• 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: 3-methoxy-N-(3-phenylpropyl)-benzamide
• 英文别名: 3-methoxy-N-(3-phenylpropyl)benzamide
• 化学式: C₁₇H₁₉NO₂
• 分子量: 269.343
• InChiKey: URSMDKUGTITLFU-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：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  间甲氧基苯甲醇 、 苯代丙腈 在 RuH₂(CO)(PPh₃)₃ 、 sodium hydride 、 1,3-diisopropylimidazolium bromide 作用下， 以 甲苯 为溶剂， 反应 48.0h， 以82%的产率得到3-methoxy-N-(3-phenylpropyl)-benzamide
  参考文献：
  名称：

  Ruthenium-Catalyzed Redox-Neutral and Single-Step Amide Synthesis from Alcohol and Nitrile with Complete Atom Economy

  摘要：

  A completely atom-economical and redox-neutral catalytic amide synthesis from an alcohol and a nitrite is realized. The amide C-N bond is efficiently formed between the nitrogen atom of nitrile and the alpha-carbon of alcohol, with the help of an N-heterocyclic carbene-based ruthenium catalyst, without a single by-product. A utility of the reaction was demonstrated by synthesizing C-13 or N-15 isotope-labeled amides without involvement of any separate reduction and oxidation step.

  DOI：

  10.1021/ja404695t

文献信息

• The effective use of substituted benzoic anhydrides for the synthesis of carboxamides
  作者：Isamu Shiina、Yo-ichi Kawakita

  DOI：10.1016/j.tet.2004.03.066

  日期：2004.5

  Various carboxamides are synthesized from the corresponding carboxylic acids and amines with high product-selectivities using 2-methyl-6-nitrobenzoic or 2,4,6-trichlorobenzoic anhydride in the presence of 4-(dimethylamino)pyridine. (C) 2004 Elsevier Ltd. All rights reserved.
• Ruthenium-Catalyzed Redox-Neutral and Single-Step Amide Synthesis from Alcohol and Nitrile with Complete Atom Economy
  作者：Byungjoon Kang、Zhenqian Fu、Soon Hyeok Hong

  DOI：10.1021/ja404695t

  日期：2013.8.14

  A completely atom-economical and redox-neutral catalytic amide synthesis from an alcohol and a nitrite is realized. The amide C-N bond is efficiently formed between the nitrogen atom of nitrile and the alpha-carbon of alcohol, with the help of an N-heterocyclic carbene-based ruthenium catalyst, without a single by-product. A utility of the reaction was demonstrated by synthesizing C-13 or N-15 isotope-labeled amides without involvement of any separate reduction and oxidation step.