N-[(4-methylphenyl)methyl]pentanamide | 550312-20-4

• 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-[(4-methylphenyl)methyl]pentanamide
• CAS: 550312-20-4
• 化学式: C₁₃H₁₉NO
• mdl: MFCD01351206
• 分子量: 205.3
• InChiKey: BKANJGNJURCJCP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.461
• 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：

  正戊酸正戊酯 、 4-甲基苄胺 在 (6-(di-tert-butylphosphinomethylene)-2-(N,N-diethylaminomethyl)-1,6-dihydropyridine)Ru(H)(CO) 作用下， 以 甲苯 、 苯 为溶剂， 反应 18.0h， 以98%的产率得到N-[(4-methylphenyl)methyl]pentanamide
  参考文献：
  名称：

  中性条件下释放H2的酯和胺合成酰胺

  摘要：

  直接由酯和胺有效合成酰胺是在温和的中性条件下实现的，并释放出分子氢。伯胺和仲胺都可以使用。这种前所未有的、普遍的、对环境无害的反应在中性条件下由脱芳构化的钌-钳形 PNN 络合物均匀催化，并在惰性气氛下在甲苯中进行，具有高周转数（高达 1000）。PNP 类似物不催化这种转化，强调了钳形配体的胺臂的重要性。提出了一种机制，涉及通过吡啶部分的芳构化-脱芳构化和胺臂的半可溶性进行金属-配体合作。

  DOI：

  10.1021/ja109944n

文献信息

• 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。
• RUTHENIUM COMPLEXES AND THEIR USES IN PROCESSES FOR FORMATION AND/OR HYDROGENATION OF ESTERS, AMIDES AND DERIVATIVES THEREOF
  申请人：Yeda Research and Development Co. Ltd.

  公开号：EP2629889B1

  公开（公告）日：2019-04-03
• US9045381B2
  申请人：——

  公开号：US9045381B2

  公开（公告）日：2015-06-02
• US9290441B2
  申请人：——

  公开号：US9290441B2

  公开（公告）日：2016-03-22