N-(1-methylhexyl)hexanamide | 543705-25-5

• 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-methylhexyl)hexanamide
• 英文别名: N-(2-heptyl)-hexanamide；N-heptan-2-ylhexanamide
• CAS: 543705-25-5
• 化学式: C₁₃H₂₇NO
• mdl: MFCD03374567
• 分子量: 213.363
• InChiKey: HYBBKKGHHJPZJO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  15
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.923
• 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：

  异庚胺 、 正己醇 在 dichloro(η6-p-cymene)(1,3-dimethylimidazole-2-ylidene)ruthenium 、 potassium tert-butylate 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以56%的产率得到N-(1-methylhexyl)hexanamide
  参考文献：
  名称：

  定义明确的N-杂环碳基钌催化剂，用于从醇和胺直接合成酰胺

  摘要：

  明确定义的基于N-杂环卡宾的钌络合物被开发为高活性催化剂，可直接由醇和胺合成酰胺。催化量的碱（例如KO t Bu）对于启动催化循环至关重要。Ru配合物的活性与报道的原位Ru催化剂相当。这些催化剂提供了机理上的见解，表明氢化钌作为一种活性催化中间体。氢化钌的生成对于游离醛的酰胺化至关重要。

  DOI：

  10.1021/om901020h

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。
• [EN] PROCESS OF FORMING AN AMIDE<br/>[FR] PROCÉDÉ DE FORMATION D'UN AMIDE
  申请人：UNIV NANYANG TECH

  公开号：WO2011034506A1

  公开（公告）日：2011-03-24

  A process is provided for the synthesis of an amide. A primary or secondary amine and a primary alcohol, with the amine and the alcohol being either moieties of different reactants or moieties of the same molecule, are contacted in the presence of a Ruthenium (II) catalyst. The Ruthenium (II) catalyst is free of a phosphine ligand. The process is also carried out in the absence of a phosphine. Providing the Ruthenium (II) catalyst includes providing an N-heterocyclic carbene.

  提供了一种合成酰胺的过程。在铑(II)催化剂的存在下，将一种初级或次级胺和一种初级醇接触，其中胺和醇可以是不同反应物的基团，也可以是同一分子的基团。铑(II)催化剂不含膦配体。该过程还在缺乏膦的情况下进行。提供铑(II)催化剂包括提供N-杂环卡宾。
• Direct Amide Synthesis from Alcohols and Amines by Phosphine-Free Ruthenium Catalyst Systems
  作者：Subhash Chandra Ghosh、Senthilkumar Muthaiah、Yao Zhang、Xiangya Xu、Soon Hyeok Hong

  DOI：10.1002/adsc.200900482

  日期：2009.11

  synthesized directly from alcohols and amines in high yields using an in situ generated catalyst from easily available ruthenium complexes such as the (p-cymene)ruthenium dichloride dimer, [Ru(p-cymeme)Cl2]2, or the (benzene)ruthenium dichloride dimer, [Ru(benzene)Cl2]2, an N-heterocyclic carbene (NHC) ligand, and a nitrogen containing L-type ligand such as acetonitrile. The phosphine-free catalyst systems showed

  使用原位生成的催化剂，由易得的钌配合物（如（p- cymene）二氯化钌二聚体，[Ru（p- cymeme）Cl 2 ] 2或（苯））直接从醇和胺中高产率直接合成酰胺。）二氯化钌二聚体，[Ru（苯）Cl 2 ] 2，N-杂环卡宾（NHC）配体和含氮L型配体（如乙腈）。与以前的基于膦的催化体系相比，无膦的催化剂体系表现出改善的或可比的活性。在原位从的[Ru（苯）氯生成催化剂2 ] 2，NHC配体和乙腈对与环状仲胺（如哌啶和吗啉）的反应具有出色的活性。
• PROCESS FOR PREPARING AMIDES FROM ALCOHOLS AND AMINES
  申请人：MILSTEIN David

  公开号：US20090112005A1

  公开（公告）日：2009-04-30

  The present invention provides a process for preparing amides, by reacting a primary amine and a primary alcohol in the presence of a Ruthenium catalyst, to generate the amide and molecular hydrogen. According to the process of the invention, primary amines are directly acylated by equimolar amounts of alcohols to produce amides and molecular hydrogen (the only byproduct) in high yields and high turnover numbers. This reaction is catalyzed by a Ruthenium complex, which is preferably based on a dearomatized PNN-type ligand of formula A1 or precursors thereof of formulae A2 or A3. Use of diamines in the reaction leads to bis-amides, whereas with a mixed primary/secondary amine substrate, chemoselective acylation of the primary amine group occurs.

  本发明提供了一种制备酰胺的方法，通过在Ruthenium催化剂的存在下反应一种一级胺和一种一级醇，生成酰胺和分子氢。根据本发明的方法，一级胺通过等摩尔量的醇直接酰化产生酰胺和分子氢（唯一的副产物），产率高，周转数高。这种反应由Ruthenium配合物催化，最好是基于公式A1的去芳香PNN型配体或其前体公式A2或A3。在反应中使用二胺会导致双酰胺，而使用混合的一级/二级胺底物，会发生一级胺基的化学选择性酰化。
• USE OF RUTHENIUM COMPLEXES FOR FORMATION AND/OR HYDROGENATION OF AMIDES AND RELATED CARBOXYLIC ACID DERIVATIVES
  申请人：Milstein David

  公开号：US20120253042A1

  公开（公告）日：2012-10-04

  A process for preparing amides by reacting a primary amine and a primary alcohol in the presence of a Ruthenium complex to generate the amide and molecular hydrogen. Primary amines are directly acylated by equimolar amounts of alcohols to produce amides and molecular hydrogen (the only byproduct) in high yields and high turnover numbers. Also disclosed are processes for hydrogenation of amides to alcohols and amines; hydrogenation of organic carbonates to alcohols; hydrogenation of carbamates or urea derivatives to alcohols and amines; amidation of esters; acylation of alcohols using esters; coupling of alcohols with water and a base to form carboxylic acids; dehydrogenation of beta-amino alcohols to form pyrazines and cyclic dipeptides; and dehydrogenation of secondary alcohols to ketones. These reactions are catalyzed by a Ruthenium complex which is based on a dearomatized PNN-type ligand of formula A1 or precursors thereof of formulae A2 or A3.

  一种制备酰胺的方法，包括在Ruthenium配合物的存在下，通过反应一种一级胺和一种一级醇生成酰胺和分子氢。直接用等摩尔量的醇对一级胺进行酰化反应，可以高产率、高周转数地生成酰胺和分子氢（唯一的副产物）。此外，还揭示了将酰胺氢化为醇和胺的方法；将有机碳酸酯氢化为醇的方法；将氨基甲酸酯或尿素衍生物氢化为醇和胺的方法；酯的酰胺化反应；使用酯对醇进行酰化反应；将醇与水和碱偶联形成羧酸；将β-氨基醇脱氢生成吡嗪和环肽；以及将二级醇脱氢生成酮的方法。这些反应由基于A1式或A2式或A3式的去芳香的PNN型配体的Ruthenium配合物催化。