N-(2-furylmethyl)hexanamide | 303092-26-4

• 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-(2-furylmethyl)hexanamide
• 英文别名: N-(furan-2-ylmethyl)hexanamide
• CAS: 303092-26-4
• 化学式: C₁₁H₁₇NO₂
• mdl: MFCD02675304
• 分子量: 195.261
• InChiKey: VUUQSNGVSRGQSZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.545
• 拓扑面积：
  42.2
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2932190090

反应信息

• 作为产物：
  描述：

  2-呋喃甲胺 、 正己醇 在 potassium tert-butylate 、 [Ru(P^tBuNNH^Bn)H(CO)Cl] 作用下， 以 乙醚 为溶剂， 50.0 ℃ 、101.33 kPa 条件下， 反应 40.0h， 以83%的产率得到N-(2-furylmethyl)hexanamide
  参考文献：
  名称：

  酰胺键的近环境温度脱氢合成：机理见解和应用

  摘要：

  目前通过胺和醇的无受体脱氢偶联合成酰胺键的方法都需要高反应温度才能有效催化，通常涉及甲苯回流，限制了其潜在的实际应用。在此，我们报道了一种使用钌 PNNH 络合物在温和条件下（乙醚回流，沸点 34.6 °C）进行该反应的系统。低温活性源于 Ru-PNNH 复合物在接近环境温度下通过末端 N-H 质子的帮助激活乙醇和半缩醛胺的能力。机理研究揭示了反应过程中出现了一种意想不到的醛结合钌物质，这也是催化静止状态。我们进一步利用低温活性，通过脱氢偶联方法从相应的胺和醇合成了几种简单的含酰胺键的市售药物。

  DOI：

  10.1021/acscatal.1c00728

文献信息

• 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。
• NOVEL RUTHENIUM COMPLEXES AND THEIR USES IN PROCESSES FOR FORMATION AND/OR HYDROGENATION OF ESTERS, AMIDES AND DERIVATIVES THEREOF
  申请人：Milstein David

  公开号：US20130281664A1

  公开（公告）日：2013-10-24

  The present invention relates to novel Ruthenium catalysts and related borohydride complexes, and the use of such catalysts, inter alia, for (1) hydrogenation of amides (including polyamides) to alcohols and amines; (2) preparing amides from alcohols with amines (including the preparation of polyamides (e.g., polypeptides) by reacting dialcohols and diamines and/or by polymerization of amino alcohols); (3) hydrogenation of esters to alcohols (including hydrogenation of cyclic esters (lactones) or cyclic di-esters (di-lactones) or polyesters); (4) hydrogenation of organic carbonates (including polycarbonates) to alcohols and hydrogenation of carbamates (including polycarbamates) or urea derivatives to alcohols and amines; (5) dehydrogenative coupling of alcohols to esters; (6) hydrogenation of secondary alcohols to ketones; (7) amidation of esters (i.e., synthesis of amides from esters and amines); (8) acylation of alcohols using esters; (9) coupling of alcohols with water to form carboxylic acids; and (10) dehydrogenation of beta-amino alcohols to form pyrazines. The present invention further relates to the novel uses of certain pyridine Ruthenium catalysts.

  本发明涉及新型钌催化剂和相关硼氢化物配合物，以及使用这些催化剂，包括：（1）将酰胺（包括聚酰胺）加氢为醇和胺；（2）用胺从醇制备酰胺（包括通过二元醇和二胺反应或氨基醇聚合制备聚酰胺（例如聚肽））；（3）将酯加氢为醇（包括环酯（内酯）或环二酯（二内酯）或聚酯的加氢）；（4）将有机碳酸酯（包括聚碳酸酯）加氢为醇和将氨基甲酸酯（包括聚氨基甲酸酯）或脲衍生物加氢为醇和胺；（5）醇的脱氢缩合成酯；（6）将二级醇加氢为酮；（7）酯的酰胺化（即从酯和胺合成酰胺）；（8）使用酯对醇进行酰化；（9）将醇与水偶联形成羧酸；以及（10）β-氨基醇的脱氢缩合形成吡嗪的新用途。本发明还涉及某些吡啶基钌催化剂的新用途。
• Practical povidone iodine catalyzed transamidation from primary amides and amines
  作者：Jian Wang、Jiangmeng Ren、Yun-Peng Zhu、Xue-Qin Sun、Peng-Fei Hu、Xin Mu、Bu-Bing Zeng

  DOI：10.1016/j.tetlet.2022.154312

  日期：2023.2

  Non-harmful Povidone iodine (PVP-I) was applied in the transamidation to gain N-substituted amides from various primary amides and amines. Diverse aromatic, heterocyclic and aliphatic primary amides/amines were applied in our developed method and more than 45 N-substituted amides were obtained with excellent yields in most cases. Several drugs such as Melatonin and Efaproxiral were successfully acquired

  将无害的聚维酮碘 (PVP-I) 应用于转酰胺基反应，以从各种伯酰胺和胺中获得N-取代的酰胺。在我们开发的方法中应用了多种芳香族、杂环族和脂肪族伯酰胺/胺，在大多数情况下以优异的收率获得了超过 45 种 N-取代的酰胺。成功获得了褪黑激素和依法普西拉等几种药物，其性能优于先前报道的结果。
• US8178723B2
  申请人：——

  公开号：US8178723B2

  公开（公告）日：2012-05-15