N-(heptan-2-yl)-2-phenylacetamide

• 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-(heptan-2-yl)-2-phenylacetamide
• 英文别名: N-(2-heptyl)-2-phenylacetamide；N-phenylacetyl-2-heptylamine；N-heptan-2-yl-2-phenylacetamide
• 化学式: C₁₅H₂₃NO
• 分子量: 233.354
• InChiKey: AXQPRWQTJNNBAO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  17
• 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：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  苯乙醇 、 异庚胺 在 吡啶 、 ruthenium trichloride 、 C₁₇H₂₅N₂⁽¹⁺⁾*I^(1-) 、 sodium hydride 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以68%的产率得到N-(heptan-2-yl)-2-phenylacetamide
  参考文献：
  名称：

  醇和胺的简单 RuCl3 催化酰胺合成

  摘要：

  开发了一种用于从胺和醇直接合成酰胺的催化剂，该催化剂由经济上有吸引力且易于获得的 RuCl 3 、N-杂环卡宾 (NHC) 和吡啶原位生成。在筛选出的 NHC 前体中，体积较小的前体对适度空间位阻的底物具有更好的产率。在寻找真正的催化中间体时，发现 Grubbs 催化剂在碱性条件下对醇的酰胺化具有活性，这表明由 NHC 配体负载的 Ru 配合物可以催化反应。

  DOI：

  10.1002/ejoc.201000362

文献信息

• Simple RuCl3-Catalyzed Amide Synthesis from Alcohols and Amines
  作者：Subhash Chandra Ghosh、Soon Hyeok Hong

  DOI：10.1002/ejoc.201000362

  日期：2010.8

  3 , an N-heterocyclic carbene (NHC), and pyridine, was developed. Of the screened NHC precursors, a less bulky one gave better yields for modestly sterically hindered substrates. In a search for the true catalytic intermediates, Grubbs catalysts were found to be active for the amidation of alcohols under basic conditions, suggesting that an Ru complex supported by an NHC ligand can catalyze the reaction

  开发了一种用于从胺和醇直接合成酰胺的催化剂，该催化剂由经济上有吸引力且易于获得的 RuCl 3 、N-杂环卡宾 (NHC) 和吡啶原位生成。在筛选出的 NHC 前体中，体积较小的前体对适度空间位阻的底物具有更好的产率。在寻找真正的催化中间体时，发现 Grubbs 催化剂在碱性条件下对醇的酰胺化具有活性，这表明由 NHC 配体负载的 Ru 配合物可以催化反应。
• 2-Furanylboronic Acid as an Effective Catalyst for the Direct Amidation of Carboxylic Acids at Room Temperature
  作者：Eric Kwok Wai Tam、Rita、Lionel Yiqian Liu、Anqi Chen

  DOI：10.1002/ejoc.201403468

  日期：2015.2

  2-Furanylboronic acid has been identified as an inexpensive and effective catalyst for the dehydrative amide formation of carboxylic acids and amines. This transformation can be efficiently carried out at room temperature and is applicable to a wide range of carboxylic acids with primary and secondary amines to afford amides in good to excellent yields.

  2-呋喃基硼酸已被确定为一种廉价且有效的催化剂，用于羧酸和胺的脱水酰胺形成。这种转化可以在室温下有效地进行，并且适用于具有伯胺和仲胺的各种羧酸，以良好到极好的收率提供酰胺。
• Penicillin acylase-catalyzed resolution of amines in aqueous organic solvents
  作者：L.M. van Langen、N.H.P. Oosthoek、D.T. Guranda、F. van Rantwijk、V.K. Švedas、R.A. Sheldon

  DOI：10.1016/s0957-4166(00)00442-0

  日期：2000.11

  Penicillin acylase from Alcaligenes faecalis catalyzes the enantioselective acylation of amines with phenylacetamide in a kinetically controlled reaction in water at pH II. Addition of cosolvent to the reaction mixture significantly improved the enantioselectivity in most cases. Penicillin acylase from E. coli also catalyzed the phenylacetylation of amines, but an order of magnitude less efficiently than with the enzyme of A. faecalis. Amine resolution via kinetically controlled acylation competes effectively with hydrolysis of N-acylated compounds and constitutes a synthetically useful alternative to existing lipase-based methods. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Fe³⁺-Montmorillonite K10: an Efficient Catalyst for Selective Amidation of Alcohols with Nitriles Under Non-Aqueous Condition
  作者：M. M. Lakouraj、B. Movassagh、J. Fasihi

  DOI：10.1080/00397910008087093

  日期：2000.3

  An efficient method for preparation of secondary amides by reaction of alcohols with nitriles is described using a catalytic amount of Fe3+-montmorillonite K10.
• N-Heterocyclic Carbene Based Ruthenium-Catalyzed Direct Amide Synthesis from Alcohols and Secondary Amines: Involvement of Esters
  作者：Cheng Chen、Yao Zhang、Soon Hyeok Hong

  DOI：10.1021/jo201756z

  日期：2011.12.16

  N-heterocyclic carbene based ruthenium complex was developed as a highly active precatalyst for the direct amide synthesis from alcohols and secondary amines. Notably, reaction of 1-hexanol and dibenzylamine afforded 60% of the corresponding amide using our catalytic system, while no amide formation was observed for this reaction with the previously reported catalytic systems. Unlike the previously reported

  明确定义的基于N-杂环卡宾的钌络合物被开发为一种高活性的预催化剂，用于由醇和仲胺直接合成酰胺。值得注意的是，使用我们的催化系统，1-己醇和二苄基胺的反应提供了60％的相应酰胺，而与先前报道的催化系统的反应没有观察到酰胺的形成。与先前报道的受较少空间受阻的醇和胺进行酰胺化反应不同，观察到酯中间体的参与。