N-(4-bromophenyl)-2-phenylpropanamide | 1174062-74-8

• 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-bromophenyl)-2-phenylpropanamide
• CAS: 1174062-74-8
• 化学式: C₁₅H₁₄BrNO
• mdl: MFCD27957043
• 分子量: 304.186
• InChiKey: OLZKROHTNRKMIX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.133
• 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：

  在 titanium(IV) isopropylate 作用下， 以 甲苯 为溶剂， 反应 2.0h， 生成 N-(4-bromophenyl)-2-phenylpropanamide
  参考文献：
  名称：

  有机碱和Cinchona基季铵盐催化下叠氮化物和可缩醛的反应

  摘要：

  在本文中，我们报告了从叠氮化物和可烯化醛开始制备酰胺的两步过程。反应通过形成三唑啉中间体进行，该中间体通过路易斯酸催化转化为酰胺。还介绍了在手性相转移催化下制备三唑啉的初步研究，表明可以从中等至低对映选择性的非手性醛制备对映体富集的酰胺。

  DOI：

  10.1039/c7ob00799j

文献信息

• Copper-catalyzed transformation of alkyl nitriles to <i>N</i>-arylacetamide using diaryliodonium salts
  作者：Romain Sallio、Pierre-Adrien Payard、Paweł Pakulski、Iryna Diachenko、Indira Fabre、Sabine Berteina-Raboin、Cyril Colas、Ilaria Ciofini、Laurence Grimaud、Isabelle Gillaizeau

  DOI：10.1039/d1ra02305e

  日期：——

  This work reports a simple and efficient method for the copper-catalyzed redox-neutral transformation of alkyl nitriles using eco-friendly diaryliodonium salts and leading to N-arylacetamides. The method features high efficiency, broad substrate scope and good functional group tolerance.

  这项工作报告了一种简单有效的方法，用于使用环保的二芳基碘鎓盐对烷基腈进行铜催化的氧化还原中性转化并生成N-芳基乙酰胺。该方法效率高、底物范围广、官能团耐受性好。
• Palladium-catalyzed amidation–hydrolysis reaction of gem-dihaloolefins: efficient synthesis of homologated carboxamides from ketones
  作者：Wenchao Ye、Jun Mo、Tiankun Zhao、Bin Xu

  DOI：10.1039/b904991f

  日期：——

  A simple and efficient palladium-catalyzed amidation–hydrolysis reaction has been developed to afford N-aryl monosubstituted carboxamides in good to excellent yields from easily accessible ketone-derived gem-dihaloolefins and aryl amines.

  我们开发出了一种简单高效的钯催化酰胺化水解反应，可以从容易获得的酮衍生宝石二卤烯烃和芳基胺中得到 N-芳基单取代羧酰胺，收率从良好到极佳。
• Highly efficient Markovnikov hydroaminocarbonylation of alkenes and alkynes catalyzed by a “soluble” heterogeneous Pd catalyst
  作者：Xin Zhou、Zhaozhan Wang、Bo Yu、Shaoping Kuang、Wei Sun、Yong Yang

  DOI：10.1039/d2gc00815g

  日期：——

  Highly efficient and regioselective synthesis of amides from simple starting materials remains a great challenge. Herein, we reported a highly efficient hydroaminocarbonylation of alkenes and alkynes with amines and CO gas catalyzed by a soluble heterogeneous Pd catalyst (Pd@PPOC), in which ultrafine Pd nanoparticles (NPs) were homogeneously dispersed in a well-defined and discrete triphenyl phosphine-built-in

  从简单的起始材料高效和区域选择性地合成酰胺仍然是一个巨大的挑战。在此，我们报道了由可溶性非均相 Pd 催化剂 (Pd@PPOC) 催化的烯烃和炔烃与胺和 CO 气体的高效氢氨基羰基化反应，其中超细 Pd 纳米颗粒 (NPs) 均匀分散在定义明确且离散的三苯基膦中- 内置多孔有机笼 (PPOC)。催化剂 Pd@PPOC 对 Markovnikov 加合物表现出优异的催化活性和区域选择性，优于之前最先进的 Pd 催化剂。以高产率合成了多种支链酰胺和 α、β-不饱和酰胺，并且底物范围广泛，涵盖了在该合成方案中具有良好耐受性的一系列官能团。值得注意的是，可溶性催化剂 Pd@PPOC 表现出高稳定性，可以很容易地分离和重复使用多达 10 次，同时保持催化性能和原始结构性质。该研究不仅提供了一种高效且可持续的酰胺合成方法，而且突出了封装在功能性 POCs 中的 MNPs 用于区域选择性催化的潜力。
• Enantioselective Synthesis of Chiral Amides by a Phosphoric Acid Catalyzed Asymmetric Wolff Rearrangement**
  作者：Jia‐Bin Pan、Zhi‐Chun Yang、Xuan‐Ge Zhang、Mao‐Lin Li、Qi‐Lin Zhou

  DOI：10.1002/anie.202308122

  日期：2023.9.25

  The highly enantioselective synthesis of chiral amides was achieved by an asymmetric Wolff rearrangement. A bifunctional phosphoric acid catalyst not only expedited the transformation but also controlled the enantioselectivity. The developed method enables the asymmetric addition between potent nucleophilic reagents and ketene species and provides a new approach to chiral amides.

  通过不对称沃尔夫重排实现了手性酰胺的高度对映选择性合成。双功能磷酸催化剂不仅能加速转化，还能控制对映选择性。所开发的方法能够实现强效亲核试剂和乙烯酮物种之间的不对称加成，并提供了一种制备手性酰胺的新方法。
• Tandem Insertion–Cyclization Reaction of Isocyanides in the Synthesis of 1,4-Diaryl-1<i>H</i>-imidazoles: Presence of<i>N</i>-Arylformimidate Intermediate
  作者：Benjamin Pooi、Jeongbin Lee、Kyujin Choi、Hajime Hirao、Soon Hyeok Hong

  DOI：10.1021/jo501652w

  日期：2014.10.3

  A straightforward and high-yielding synthesis of 1,4-diaryl-1H-imidazoles is reported. 1,4-Diaryl-1H-imidazoels have been difficult to access in ambient conditions, but our method utilizes two different facets of isocyanide reactivity to achieve it. The reaction is believed to involve (1) NHC-copper-catalyzed isocyanide insertion into alcohol to form an N-arylformimidate intermediate and (2) subsequent base-promoted cycloaddition with benzyl isocyanide derivatives There is cooperation between these two processes through the deprotonation of benzyl isocyanide by KOtBu. The deprotonation gives tert-butyl alcohol and the benzyl isocyanide anion which are used for the first and second steps of the reaction, respectively. Various control and kinetic experiments were carried out to gain an in-depth understanding of the reaction mechanism and isocyanide reactivity. The reaction mechanism determined by density functional theory calculations was consistent with the experimental data and provided detailed explanations for the reactivity trends.