N,N-dimethyl-3-(naphthalen-1-yl)propanamide | 27563-33-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N,N-dimethyl-3-(naphthalen-1-yl)propanamide
• 英文别名: N,N-Dimethyl-3-(1-naphthyl)-propanamide；N,N-dimethyl-3-naphthalen-1-ylpropanamide
• CAS: 27563-33-3
• 化学式: C₁₅H₁₇NO
• 分子量: 227.306
• InChiKey: OKHFTNAGQWSGDY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  N,N-二甲基乙酰胺 、 1-萘甲醇 在 potassium tert-butylate 作用下， 以 均三甲苯 为溶剂， 反应 6.0h， 以74%的产率得到N,N-dimethyl-3-(naphthalen-1-yl)propanamide
  参考文献：
  名称：

  苄醇与乙酰胺之间的自由基缩合形成3-芳基丙酰胺

  摘要：

  开发了一种新的自由基缩合反应，其中将苄醇和乙酰胺偶联以生成3-芳基丙酰胺，而水是唯一的副产物。用叔丁醇钾作为唯一添加剂进行转化，并以高收率产生各种3-芳基丙酰胺。已通过标记底物，捕获实验和光谱测量对这种机理进行了实验研究。研究结果表明自由基途径，其中钾叔据信-丁醇盐起碱和自由基引发剂的双重作用。提出了苄醇的自由基阴离子作为关键中间体，该中间体与酰胺的烯酸酯进行偶联形成新的C–C键。随后消除为相应的肉桂酰胺，然后烯烃还原得到3-芳基丙酰胺。

  DOI：

  10.1039/d0sc02948c

文献信息

• General and Mild Cobalt-Catalyzed C-Alkylation of Unactivated Amides and Esters with Alcohols
  作者：Nicklas Deibl、Rhett Kempe

  DOI：10.1021/jacs.6b06448

  日期：2016.8.31

  The borrowing hydrogen or hydrogen autotransfer methodology is an elegant and sustainable or green concept to construct carbon-carbon bonds. In this concept, alcohols, which can be obtained from barely used and indigestible biomass, such as lignocellulose, are employed as alkylating reagents. An especially challenging alkylation is that of unactivated esters and amides. Only noble metal catalysts based

  借用氢或氢自动转移方法是构建碳-碳键的优雅且可持续或绿色的概念。在这个概念中，可以从几乎不使用且难以消化的生物质（例如木质纤维素）中获得的醇被用作烷基化试剂。一个特别具有挑战性的烷基化是未活化的酯和酰胺。仅使用基于铱和钌的贵金属催化剂来完成这些反应。在此，我们报告了醇对未活化酰胺和酯的第一个贱金属催化的 α-烷基化反应。我们实验室最近开发的钳形配体稳定的钴配合物可以非常有效地催化这些反应。预催化剂可以很容易地从市售的起始材料以多克规模合成，并且在碱性反应条件下自活化。这种 Co 催化剂类别还能够介导酯和酰胺的烷基化反应。此外，我们应用该方法合成酮并将醇转化为由两个碳原子拉长的醛。
• Sustainable Alkylation of Unactivated Esters and Amides with Alcohols Enabled by Manganese Catalysis
  作者：Yoon Kyung Jang、Tobias Krückel、Magnus Rueping、Osama El-Sepelgy

  DOI：10.1021/acs.orglett.8b03184

  日期：2018.12.21

  The first example of manganese-catalyzed C-alkylation of the carboxylic acid derivatives is reported. The bench-stable homogeneous manganese complex enables the transformation of the renewable alcohol and carboxylic acid derivative feedstock to higher value esters and amides. The reaction operates via hydrogen autotransfer and ideally produces water as the only side product. Importantly, aliphatic-

  报道了羧酸衍生物的锰催化的C-烷基化的第一个实例。台式稳定的均相锰配合物可以将可再生的醇和羧酸衍生物原料转化为更高价值的酯和酰胺。该反应通过氢自动转移进行，理想地产生水作为唯一的副产物。重要的是，可以将含脂肪族，苄基和杂环的醇用作烷基化试剂，从而消除了对诱变的烷基卤化物的需求。
• Nickel-catalyzed <i>C</i>-alkylation of thioamide, amides and esters by primary alcohols through a hydrogen autotransfer strategy
  作者：Peng Yang、Xiuhua Wang、Yu Ma、Yaxin Sun、Li Zhang、Jieyu Yue、Kaiyue Fu、Jianrong Steve Zhou、Bo Tang

  DOI：10.1039/d0cc06468h

  日期：——

  A simple catalyst of Ni(OAc)2 and P(t-Bu)3 enables selective C-alkylation of thioacetamides and primary acetamide with alcohols for the first time. Monoalkylation of thioamides, amides and t-butyl esters occurs in excellent yields (>95%). Mechanistic studies reveal that the reaction proceeds via a hydrogen autotransfer pathway.

  Ni（OAc）2和P（t-Bu）3的简单催化剂使硫代乙酰胺和伯乙酰胺与醇的选择性C-烷基化首次实现。硫代酰胺，酰胺和叔丁基酯的单烷基化以极高的收率（> 95％）发生。机理研究表明，反应通过氢自动转移途径进行。
• Ruthenium hydride/nitrogen tridentate ligand-catalyzed α-alkylation of acetamides with primary alcohols
  作者：Takashi Kuwahara、Takahide Fukuyama、Ilhyong Ryu

  DOI：10.1039/c3ra42834f

  日期：——

  The α-alkylation reaction of acetamides with primary alcohols to afford the corresponding amides was accomplished effectively using RuHCl(CO)(PPh3)3 as a catalyst, nitrogen tridentate ligand L1 as an additive, and KOtBu as a base. While the addition of bpy was effective only for benzylic alcohols, L1 affected the alkylation reaction when both benzylic and non-benzylic type alcohols were used.

  使用RuHCl(CO)(PPh3)3作为催化剂、氮三齿配体L1作为添加剂和KOtBu作为碱，成功实现了醋酰胺与初级醇的α-烷基化反应，以生成相应的酰胺。虽然bpy的添加仅对苄醇有效，但当使用苄醇和非苄醇类型的醇时，L1对烷基化反应产生了影响。
• [EN] QUINOLINE DERIVATIVES AND THEIR USE AS MYCOBACTERIAL INHIBITORS<br/>[FR] DERIVES DE QUINOLEINE ET LEUR UTILISATION EN TANT QU'INHIBITEURS MYCOBACTERIENS
  申请人：JANSSEN PHARMACEUTICA NV

  公开号：WO2004011436A1

  公开（公告）日：2004-02-05

  The present invention relates to novel substituted quinoline derivatives according to the general Formula (Ia) or the general Formula (Ib), the pharmaceutically acceptable acid or base addition salts thereof, the stereochemically isomeric forms thereof, the tautomeric forms thereof and the N-oxide forms thereof. The claimed compounds are useful for the treatment of mycobacterial diseases, particularly those diseases caused by pathogenic mycobacteria such as Mycobacterium tuberculosis, M. bovis, M. avium and M. marinum. In particular, compounds are claimed in which, independently from each other, R1 is bromo, p=1, R2 is alkyloxy, R3 is optionally substituted naphthyl or phenyl, q=1, R4 and R5 each independently are hydrogen, methyl or ethyl, R6 is hydrogen, r is equal to 0 or 1 and R7 is hydrogen. Also claimed is a composition comprising a pharmaceutically acceptable carrier and, as active ingredient, a therapeutically effective amount of the claimed compounds, the use of the claimed compounds or compositions for the manufacture of a medicament for the treatment of mycobacterial diseases and a process for preparing the claimed compounds.

  本发明涉及根据通式(Ia)或通式(Ib)的新型取代喹啉衍生物，其药学上可接受的酸盐或碱盐，其立体化学异构体形式，其互变异构体形式和其N-氧化物形式。所述化合物对治疗结核分枝杆菌病等由病原性分枝杆菌引起的疾病有用，特别是对治疗结核分枝杆菌、博维氏分枝杆菌、埃维分枝杆菌和海洋分枝杆菌等疾病有用。特别地，所述化合物中，独立于彼此，R1为溴，p=1，R2为烷氧基，R3为可选择取代的萘基或苯基，q=1，R4和R5各自独立为氢、甲基或乙基，R6为氢，r等于0或1，R7为氢。还声明了一种包含药学上可接受载体和作为活性成分的所述化合物的治疗有效量的组合物，所述化合物或组合物用于制备治疗结核分枝杆菌病的药物以及制备所述化合物的方法。