2-phenyl-N-(pyridin-2-ylmethyl)acetamide | 92244-99-0

• 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: 2-phenyl-N-(pyridin-2-ylmethyl)acetamide
• 英文别名: 2-phenyl-N-(pyridine-2-ylmethyl)acetamide；Benzeneacetamide, N-(2-pyridinylmethyl)-
• CAS: 92244-99-0
• 化学式: C₁₄H₁₄N₂O
• 分子量: 226.278
• InChiKey: YJSICNKSIVITMJ-UHFFFAOYSA-N

物化性质

• 熔点：
  105-106 °C(Solv: toluene (108-88-3))
• 沸点：
  460.7±38.0 °C(Predicted)
• 密度：
  1.139±0.06 g/cm3(Predicted)
• 溶解度：
  >33.9 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  42
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-phenyl-N-(pyridin-2-ylmethyl)acetamide 在 碘苯二乙酸 、 palladium diacetate 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以78%的产率得到1-(pyridin-2-ylmethyl)-3H-indol-2-one
  参考文献：
  名称：

  通过钯催化的未活化γC（sp3）分子内胺化反应，使用易于除去的辅助基团合成吡咯烷酮吗？H债券

  摘要：

  容易上手，容易下手：发现可促进仲酰胺的钯催化的γC（sp 3）H和C（sp 2）H键的钯催化胺化反应，包括5-甲氧基-8-氨基喹啉，可将其除去在温和条件下（请参阅方案； CAN =硝酸硝酸铈）。结合使用β- CH甲基化或γ- CH芳基化步骤，可以使γ-C（sp 3）H胺化反应从易得的前体中获得复杂的吡咯烷酮。

  DOI：

  10.1002/anie.201305615
• 作为产物：
  描述：

  苯乙酸 在 碘 、 zinc trifluoromethanesulfonate 作用下， 以 乙腈 为溶剂， 反应 4.67h， 生成 2-phenyl-N-(pyridin-2-ylmethyl)acetamide
  参考文献：
  名称：

  Zn(OTf)₂-Promoted Chemoselective Esterification of Hydroxyl Group Bearing Carboxylic Acids

  摘要：

  Selective esterification of aliphatic and aromatic carboxylic acids with various alcohols is studied using triphenylphosphine, I-2, and a catalytic amount of Zn(OTf)(2). Use of this catalyst allows the formation of esters at a faster rate with good to excellent yield by activating the in situ generated acyloxyphosphonium ion intermediate. During the esterification process, both their aromatic and aliphatic hydroxyl groups are fully preserved from trans-esterification. The results show that the bulkiness and the reactivity of this doubly activated intermediate III control the selectivity and the rate of the reaction, respectively. The method is also useful for direct amidation reactions.

  DOI：

  10.1021/jo302502r

文献信息

• Metal-Free C–C Coupling of an Allenyl Sulfone with Picolyl Amides to Access Vinyl Sulfones via Pyridine-Initiated In Situ Generation of Sulfinate Anion
  作者：Humair M. Omer、Peng Liu、Kay M. Brummond

  DOI：10.1021/acs.joc.0c00788

  日期：2020.6.19

  Vinyl sulfones are privileged motifs known for their biological activity and synthetic utility. Synthetic transformations to efficiently access high-value compounds with these motifs are desired and sought after. Herein, a new procedure is described to form vinyl sulfone-containing compounds by selective functionalization of the C(sp3)–H bond adjacent to the pyridine ring of pharmacologically prevalent

  乙烯基砜因其生物学活性和合成用途而享有特权。合成转化以有效地获得具有这些基序的高价值化合物是人们所期望和追求的。在本文中，描述了一种新的方法，可通过药理学上普遍的甲基吡啶酰胺的吡啶环附近的C（sp 3）-H键与烯基砜1-甲基-4-（丙基）的选择性官能化来形成含乙烯基砜的化合物-1,2-二烯-1-基磺酰基）苯。反应条件温和，不需要金属催化剂或添加剂，并且显示出良好的官能团耐受性。对于这种异常转化的机理研究表明，该反应通过罕见的吡啶引发的p-甲苯磺酸根阴离子介导的烯丙基砜的活化，类似于膦触发的反应。
• Multinuclear copper complexes of pyridylmethylamide ligands
  作者：Urmila Pal Chaudhuri、Laura R. Whiteaker、Lei Yang、Robert P. Houser

  DOI：10.1039/b513763b

  日期：——

  Copper complexes of a family of pyridylmethylamide ligands HLPh, HLMe3 and HLPh3 were synthesized and characterized [HLPh = 2-phenyl-N-(2-pyridylmethyl)acetamide; HLMe3 = 2,2-dimethyl-N-(2-pyridylmethyl)propionamide; HLPh3 = 2,2,2-triphenyl-N-(2-pyridylmethyl)acetamide]. The reaction of copper(II) salts with the HL family and triethylamine in methanol yields copper(II) complexes [Cu4(LPh)4(OH)2](ClO4)2 (1), [Cu2(HLMe3)2(OMe)2(MeOH)2](OTf)2 (2) and [Cu2(HLPh3)2(OMe)2(MeOH)2](OTf)2 (3). The complexes have different nuclearity owing to varying steric properties of the ligands used. Complex 1 self-assembles in the presence of excess base to form a tetranuclear complex. Complexes 2 and 3 are binuclear and are bridged by a pair of methoxide ligands. Steric encumbrance of the ligands in 2 and 3 prevent cluster formation.

  合成并表征了一系列吡啶甲基胺配体的铜络合物，分别为 HLPh、HLMe3 和 HLPh3 [HLPh = 2-苯基-N-(2-吡啶甲基)乙酰胺；HLMe3 = 2,2-二甲基-N-(2-吡啶甲基)丙酰胺；HLPh3 = 2,2,2-三苯基-N-(2-吡啶甲基)乙酰胺]。铜(II)盐与 HL 系列配体和三乙胺在甲醇中反应，得到铜(II)络合物 [Cu4(LPh)4(OH)2](ClO4)2 (1)、[Cu2(HLMe3)2(OMe)2(MeOH)2](OTf)2 (2) 和 [Cu2(HLPh3)2(OMe)2(MeOH)2](OTf)2 (3)。由于所用配体的立体性质不同，这些络合物具有不同的核数。络合物 1 在多余的碱存在下自组装形成四核络合物。络合物 2 和 3 为双核络合物，由一对甲氧基配体桥接。配体在 2 和 3 中的空间位阻限制了簇的形成。
• Direct amidation of non‐activated carboxylic acid and amine derivatives catalyzed by TiCp ₂ Cl ₂
  作者：Hui Wang、Wei Dong、Zhipeng Hou、Lidan Cheng、Xiufen Li、Longjiang Huang

  DOI：10.1002/aoc.5568

  日期：2020.5

  carboxylic acid and amine derivatives catalyzed by TiCp2Cl2. Arylacetic acid derivatives reacted with different amines to afford the corresponding amides in good to excellent yield except of aniline. Aryl formic acids failed to react with aniline but smoothly reacted with aliphatic amines and benzylamine in moderate to good yield, fatty acids reacting with benzyl and aliphatic amines give amides in good

  本文描述了由TiCp 2 Cl 2催化的非活化羧酸和胺衍生物的温和有效直接酰胺化反应。丁二酸衍生物与不同的胺反应以除苯胺以外的良好至优异的产率提供相应的酰胺。芳基甲酸不能与苯胺反应，但是可以与脂肪胺和苄胺平滑反应，收率中等至良好；脂肪酸与苄基和脂肪胺反应可以得到酰胺，收率很好。手性氨基酸衍生物无需外消旋就可以中等产率转化为酰胺。TiCp 2 Cl 2催化直接酰胺化的可能机理进行了讨论。该催化方法非常适用于低位阻芳基丙烯酸，除苯胺以外的具有不同低位阻胺的脂肪酸的酰胺化，以及芳基甲酸与苄基和脂族胺的酰胺化。
• Direct Amidation of Carboxylic Acids Catalyzed by <i>ortho</i>-Iodo Arylboronic Acids: Catalyst Optimization, Scope, and Preliminary Mechanistic Study Supporting a Peculiar Halogen Acceleration Effect
  作者：Nicolas Gernigon、Raed M. Al-Zoubi、Dennis G. Hall

  DOI：10.1021/jo3013258

  日期：2012.10.5

  synthetic products motivates the development of catalytic, direct amidation methods employing free carboxylic acids and amines that circumvent the need for stoichiometric activation or coupling reagents. ortho-Iodophenylboronic acid 4a has recently been shown to catalyze direct amidation reactions at room temperature in the presence of 4A molecular sieves as dehydrating agent. Herein, the arene core of ortho-iodoarylboronic

  酰胺作为生物分子和合成产物的组成部分的重要性促使人们开发使用游离羧酸和胺的催化，直接酰胺化方法，从而避免了对化学计量活化或偶合试剂的需求。最近已显示，在存在作为脱水剂的4A分子筛的情况下，邻-碘苯基硼酸4a在室温下催化直接酰胺化反应。在这里，邻域的芳烃核心关于环取代的电子效应，已经优化了-碘芳基硼酸催化剂。与预期相反，发现给电子取代基是优选的，特别是在碘化物对位的烷氧基取代基。最佳新催化剂5-甲氧基-2-碘苯基硼酸（MIBA，4f）在动力学上比母体去甲氧基催化剂4a具有更高的活性，在温和条件下于室温下以较短的反应时间提供了更高的酰胺产物收率。温度。催化剂4f可被回收利用并促进由脂肪族羧酸和胺，杂芳族羧酸和其他含有游离酚，吲哚和吡啶等部分的官能化底物形成酰胺。机理研究证明了分子筛在这种复杂的酰胺化过程中的重要作用。底物化学计量，浓度和催化剂阶数的测量结果导致了基于假定的酰基硼酸酯中间体的可能
• Neutral pyridylmethylamide ligands and their mononuclear copper(II) complexes
  作者：Urmila Pal Chaudhuri、Lei Yang、Laura R. Whiteaker、Arunendu Mondal、Matthew R. Fultz、Douglas R. Powell、Robert P. Houser

  DOI：10.1016/j.poly.2007.08.004

  日期：2007.11

  Mononuclear copper(II) complexes of a family of pyridylmethylamide ligands HL, HLMe, HLPh, HLMe3 and HLPh3, [HL = N-(2-pyridylmethyl)acetamide; HLMe = N-(2-pyridylmethyl)propionamide; HLPh = 2-phenyl-N-(2-pyridylmethyl)acetamide; HLMe3 = 2, 2-dimethyl-N-(2-pyridyhnethyl)propionamide; HLPh3 = 2,2,2-triphenyl-N-(2-pyridylmethyl)acetamide], were synthesized and characterized. The reaction of copper(II) salts with the pyridylmethylamide ligands yields complexes [Cu(HL)(2)(OTf)(2)] (1), [Cu(HLMe)(2)](ClO4)(2) (2), [Cu(HL)(2)Cl](2)[CuCl4] (3), [Cu(HLMe3)(2)(THF)](OTf)(2) (4), [Cu(HLMe3)(2)(H2O)](ClO4)(2) (5a and 5b), [Cu(HLPh3)(2)(H2O)](ClO4)(2) (6), [Cu(HL)(2,2'-bipy)(H2O)](ClO4)(2) (7), and [Cu(HLPh)(2,2'-bipy)(H2O)](ClO4)(2) (8). All complexes were fully characterized, and the X-ray structures vary from four-coordinate square-planar, to five-coordinate square-pyramidal or trigonal-bipyramidal. The neutral ligands coordinate via the pyridyl N atom and carbonyl 0 atom in a bidentate fashion. The spectroscopic properties are typical of mononuclear copper(II) species with similar ligand sets, and are consistent their X-ray structures. (C) 2007 Elsevier Ltd. All rights reserved.