N-(1-phenylethyl)hexanamide | 19145-73-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: N-(1-phenylethyl)hexanamide
• CAS: 19145-73-4；78172-89-1
• 化学式: C₁₄H₂₁NO
• mdl: MFCD01336962
• 分子量: 219.327
• InChiKey: DGNYVUGHUGTLTE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  己酰胺 、 α-苯乙胺 在 niobium(V) oxide 作用下， 以 neat (no solvent) 为溶剂， 以91%的产率得到N-(1-phenylethyl)hexanamide
  参考文献：
  名称：

  介孔氧化铌球作为伯酰胺与胺转氨的有效催化剂

  摘要：

  AbstractMesoporous niobium oxide spheres (MNOS), conveniently prepared by a novel antisolvent precipitation approach, have been shown to be an effective catalyst for the transamidation of primary amides with amines. This novel transamidation can be efficiently carried out under solvent‐free conditions and is applicable to a wide range of primary amides and amines to provide N‐alkyl amides in good to excellent yields. The catalyst is highly stable and reusable. The application of this transamidation reaction has been demonstrated in the synthesis of antidepressant drug moclobemide and other drug‐like compounds.magnified image

  DOI：

  10.1002/adsc.201300717

文献信息

• A CONVENIENT METHOD FOR THE SYNTHESIS OF CARBOXAMIDES AND PEPTIDES BY THE USE OF TETRABUTYLAMMONIUM SALTS
  作者：Yutaka Watanabe、Teruaki Mukaiyama

  DOI：10.1246/cl.1981.285

  日期：1981.3.5

  aqueous THF with bis(o-nitrophenyl) phenylphosphonate in the presence of tetrabutylammonium hydrogen sulfate or bromide. Carboxylic esters are also successfully converted to amides via carboxylate salts in one-pot.

  在四丁基硫酸氢铵或溴化铵存在下，用双（邻硝基苯基）苯基膦酸酯处理 H2O-二氯甲烷或 THF 水溶液中的游离酸和胺，以良好的收率制备各种甲酰胺和肽。羧酸酯也可以通过羧酸盐在一锅法中成功转化为酰胺。
• Polyoxometalate–Ionic Liquid-Catalyzed Ritter Reaction for Efficient Synthesis of Amides
  作者：Lan-Cui Zhang、Shuang Gao、Lei Zhang、Bo Chen、Peipei He、Guosong Li

  DOI：10.1055/a-1854-9958

  日期：2022.9

  acidity and miscibility, have been developed to promote the Ritter reaction. Among them, [BSmim]CuPW12O40 [BSmim = 1-methyl-3-(4-sulfobutyl)-1H-imidazol-3-ium] displayed the highest activity for the amidation of a variety of alcohols with nitriles, delivering the corresponding amide products in good to excellent yields. Furthermore, the reaction can be easily scaled up to a gram scale without losing efficiency

  已经开发了一系列多金属氧酸盐-离子液体催化剂，结合了多金属氧酸盐和离子液体的特性，并引入了酸性和混溶性，以促进 Ritter 反应。其中，[BSmim]CuPW 12 O 40 [BSmim = 1-methyl-3-(4-sulfobutyl)-1 H -imidazol -3-ium]对多种醇与腈的酰胺化活性最高，相应的酰胺产品的收率很好。此外，反应可以很容易地放大到克级，而不会损失效率。因此，该方法提供了一种使用多金属氧酸盐-离子液体基催化剂通过 Ritter 反应制备酰胺的有吸引力的方法。
• Electrochemical Oxidative C–H Amination through a Ritter-Type Reaction
  作者：Yiwen Xu、Qiang Li、Runyou Ye、Buyi Xu、Xiangge Zhou

  DOI：10.1021/acs.joc.3c00609

  日期：2023.7.7

  A straightforward strategy for direct benzylic C–H bond amination via an electrochemical Ritter-type reaction is developed. The reaction demonstrates simpler and milder reaction conditions over the existing methods without extra mediator. Moderate to excellent yields up to 94% of the desired amide products were obtained with a broad substrate scope. The removal of the Ac group by a simple step can

  开发了一种通过电化学 Ritter 型反应直接进行苄基 C-H 键胺化的简单策略。该反应比现有方法表现出更简单、更温和的反应条件，无需额外的介体。在广泛的底物范围内获得了中等至优异的收率，高达 94% 的所需酰胺产物。通过简单的步骤去除Ac基团可以得到不含NH的苄胺，为生物活性分子的后期功能化提供了合适的方法。
• Mesoporous Niobium Oxide Spheres as an Effective Catalyst for the Transamidation of Primary Amides with Amines
  作者：Subhash Chandra Ghosh、Cheng Chao Li、Hua Chun Zeng、Joyce S. Y. Ngiam、Abdul M. Seayad、Anqi Chen

  DOI：10.1002/adsc.201300717

  日期：2014.2.10

  AbstractMesoporous niobium oxide spheres (MNOS), conveniently prepared by a novel antisolvent precipitation approach, have been shown to be an effective catalyst for the transamidation of primary amides with amines. This novel transamidation can be efficiently carried out under solvent‐free conditions and is applicable to a wide range of primary amides and amines to provide N‐alkyl amides in good to excellent yields. The catalyst is highly stable and reusable. The application of this transamidation reaction has been demonstrated in the synthesis of antidepressant drug moclobemide and other drug‐like compounds.magnified image