(R)-4-bromo-N-(1-phenylethyl)benzamide

• 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: (R)-4-bromo-N-(1-phenylethyl)benzamide
• 英文别名: 4-bromo-N-[(1R)-1-phenylethyl]benzamide
• 化学式: C₁₅H₁₄BrNO
• 分子量: 304.186
• InChiKey: HYHSCLDDJSDEQE-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 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

• 作为反应物：
  描述：

  (R)-4-bromo-N-(1-phenylethyl)benzamide 在 四(三苯基膦)钯 、 正丁基锂 、 potassium carbonate 作用下， 以 四氢呋喃 、 水 、 甲苯 为溶剂， 反应 16.5h， 生成 (R)-3',5'-diformyl-4'-hydroxy-N-(1-phenylethyl)-[1,1'-biphenyl]-4-carboxamide
  参考文献：
  名称：

  ‘Double chiral’ new members of calixsalen family

  摘要：

  Synthesis and X-ray diffraction studies on the first examples of 'double chiral' calixsalens are presented. In these molecules, one can clearly distinguish two chiral zones. The first one is made by the macrocycle base, whereas the second chiral zone is set up of the additional chirality elements in the tail of the molecule. The 'double chiral' calixsalens are formed through cyclocondensation between chiral vicinal diamine of trans-1,2-diaminocyclohexane type and chiral C-5 substituted 2-hydroxyisophthalaldehyde derivatives. The absolute configuration of the dialdehyde did not affect the yield of the macrocyclization reaction. The presence of secondary amides in the tail part of the macrocycle leads to formation of hydrogen bonding network in the solid state, while sterical hindrance preserve interdigitation, thus, 'double chiral' calixsalens do not form aggregates typical for other calixsalens. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2017.08.021
• 作为产物：
  描述：

  4-溴苯甲酸 在 氯化亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 (R)-4-bromo-N-(1-phenylethyl)benzamide
  参考文献：
  名称：

  ‘Double chiral’ new members of calixsalen family

  摘要：

  Synthesis and X-ray diffraction studies on the first examples of 'double chiral' calixsalens are presented. In these molecules, one can clearly distinguish two chiral zones. The first one is made by the macrocycle base, whereas the second chiral zone is set up of the additional chirality elements in the tail of the molecule. The 'double chiral' calixsalens are formed through cyclocondensation between chiral vicinal diamine of trans-1,2-diaminocyclohexane type and chiral C-5 substituted 2-hydroxyisophthalaldehyde derivatives. The absolute configuration of the dialdehyde did not affect the yield of the macrocyclization reaction. The presence of secondary amides in the tail part of the macrocycle leads to formation of hydrogen bonding network in the solid state, while sterical hindrance preserve interdigitation, thus, 'double chiral' calixsalens do not form aggregates typical for other calixsalens. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2017.08.021

文献信息

• Microwave-Assisted Acylation of Amines, Alcohols, and Phenols by the Use of Solid-Supported Reagents (SSRs)
  作者：Elena Petricci、Claudia Mugnaini、Marco Radi、Federico Corelli、Maurizio Botta

  DOI：10.1021/jo048837q

  日期：2004.11.1

  A microwave-assisted synthesis of solid-supported reagents for the acylation of amines has been developed, and the same methodology has been successfully applied to the preparation of acylating agents anchored on different solid supports. Similarly, alcohols, phenols, and thiophenols have been easily acylated using these reagents under microwave irradiation.

  已经开发了微波辅助的用于胺的酰化的固体负载试剂的合成，并且相同的方法已经成功地应用于制备锚定在不同固体载体上的酰化剂。类似地，使用这些试剂在微波辐射下很容易将醇，酚和硫酚酰化。
• <i>N</i>-Heterocyclic Carbene-Mediated Microfluidic Oxidative Electrosynthesis of Amides from Aldehydes
  作者：Robert A. Green、Derek Pletcher、Stuart G. Leach、Richard C. D. Brown

  DOI：10.1021/acs.orglett.6b00339

  日期：2016.3.4

  A flow process for N-Heterocyclic Carbene (NHC)-mediated anodic oxidative amidation of aldehydes is described, employing an undivided microfluidic electrolysis cell to oxidize Breslow intermediates. After electrochemical oxidation, the reaction of the intermediate N-acylated thiazolium cation with primary amines is completed by passage through a heating cell to achieve high conversion in a single pass

  描述了一种N-杂环卡宾（NHC）介导的醛的阳极氧化酰胺化的工艺，该工艺采用未分开的微流体电解槽氧化Breslow中间体。电化学氧化后，中间体N-酰化噻唑鎓阳离子与伯胺的反应通过通过加热单元以单次实现高转化率来完成。流动混合方案避免了醛和胺底物之间竞争性亚胺形成的问题，否则将阻止所需产物的形成。对于19种酰胺，实现了高收率（71–99％），生产率（高达2.6 gh –1）和电流效率（65–91％）。
• Enantioselective Intermolecular Radical Amidation and Amination of Benzylic C−H Bonds via Dual Copper and Photocatalysis
  作者：Xuemeng Chen、Zhong Lian、Søren Kramer

  DOI：10.1002/anie.202217638

  日期：2023.3.20

  A method for enantioselective intermolecular benzylic C−H amidation and amination is reported. This dehydrogenative C−N bond formation displays broad substrate scope and good atom economy, is amenable to late-stage C−H functionalization, and enables easy access to 15N-labeling from cheap [15N]-NH4Cl.

  报道了一种对映选择性分子间苄基 C−H 酰胺化和胺化的方法。这种脱氢 C−N 键形成显示出广泛的底物范围和良好的原子经济性，适用于后期 C−H 功能化，并且能够从廉价的 [ 15 N]-NH 4 Cl轻松获得15 N-标记。
• A Dual-Catalysis Anion-Binding Approach to the Kinetic Resolution of Amines: Insights into the Mechanism via a Combined Experimental and Computational Study
  作者：Nisha Mittal、Katharina M. Lippert、Chandra Kanta De、Eric G. Klauber、Thomas J. Emge、Peter R. Schreiner、Daniel Seidel

  DOI：10.1021/jacs.5b00190

  日期：2015.5.6

  Racemic benzylic amines undergo kinetic resolution via benzoylation with benzoic anhydride in the presence of a dual catalyst system consisting of a readily available amide-thiourea catalyst and 4-dimethylaminopyridine (DMAP). An evaluation of various experimental parameters was performed in order to derive a more detailed understanding of what renders this process selective. The catalyst's aggregation behavior and anion-binding ability were evaluated in regard to their relevance for the catalytic process. Alternate scenarios, such as catalyst deprotonation or the in situ formation of a neutral chiral acylating reagent were ruled out. Detailed computational studies at the M06/6-31G(d,p) level of theory including solvent modeling utilizing a polarized continuum model provide additional insights into the nature of the ion pair and reveal a range of important secondary interactions that are responsible for efficient enantiodiscrimination.
• ‘Double chiral’ new members of calixsalen family
  作者：Małgorzata Petryk、Agnieszka Janiak、Marcin Kwit

  DOI：10.1016/j.tetasy.2017.08.021

  日期：2017.10

  Synthesis and X-ray diffraction studies on the first examples of 'double chiral' calixsalens are presented. In these molecules, one can clearly distinguish two chiral zones. The first one is made by the macrocycle base, whereas the second chiral zone is set up of the additional chirality elements in the tail of the molecule. The 'double chiral' calixsalens are formed through cyclocondensation between chiral vicinal diamine of trans-1,2-diaminocyclohexane type and chiral C-5 substituted 2-hydroxyisophthalaldehyde derivatives. The absolute configuration of the dialdehyde did not affect the yield of the macrocyclization reaction. The presence of secondary amides in the tail part of the macrocycle leads to formation of hydrogen bonding network in the solid state, while sterical hindrance preserve interdigitation, thus, 'double chiral' calixsalens do not form aggregates typical for other calixsalens. (C) 2017 Elsevier Ltd. All rights reserved.