(R)-4-甲基-N-(1-苯乙基)苯甲酰胺 | 404942-59-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (R)-4-甲基-N-(1-苯乙基)苯甲酰胺
• 英文名称: (R)-4-methyl-N-(1-phenylethyl)benzamide
• 英文别名: 4-Methyl-N-(1-phenyl-ethyl)-benzamide；4-methyl-N-[(1R)-1-phenylethyl]benzamide
• CAS: 404942-59-2
• 化学式: C₁₆H₁₇NO
• 分子量: 239.317
• InChiKey: QYZVNRJWKFCVMG-CYBMUJFWSA-N

物化性质

• 熔点：
  133-135 °C
• 沸点：
  415.1±34.0 °C(Predicted)
• 密度：
  1.068±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 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：

  n-苄基苯甲酰胺 、 (R)-4-甲基-N-(1-苯乙基)苯甲酰胺 在 N-苄基二乙酰胺 、 potassium hydride 作用下， 以 二乙二醇二甲醚 为溶剂， 反应 18.0h， 生成 N-苄基-4-甲基苯甲酰胺 、 (R)-(+)-N-苯甲酰-Alpha-甲基苯胺
  参考文献：
  名称：

  简单仲酰胺的催化复分解。

  摘要：

  DOI：

  10.1002/anie.200603588
• 作为产物：
  描述：

  4-甲基苯甲酸酐 、 α-苯乙胺 在 4-二甲氨基吡啶 、 N-((1R,2R)-2-(3-(3,5-bis(trifluoromethyl)phenyl)thioureido)cyclohexyl)-3,5-bis(trifluoromethyl)benzamide 作用下， 以 甲苯 为溶剂， 反应 2.25h， 生成 (R)-4-甲基-N-(1-苯乙基)苯甲酰胺
  参考文献：
  名称：

  A Dual-Catalysis Anion-Binding Approach to the Kinetic Resolution of Amines: Insights into the Mechanism via a Combined Experimental and Computational Study

  摘要：

  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.

  DOI：

  10.1021/jacs.5b00190

文献信息

• Nickel‐Catalyzed Asymmetric Synthesis of α‐Arylbenzamides
  作者：Sergio Cuesta‐Galisteo、Johannes Schörgenhumer、Xiaofeng Wei、Estíbaliz Merino、Cristina Nevado

  DOI：10.1002/anie.202011342

  日期：2021.1.18

  A nickel‐catalyzed asymmetric reductive hydroarylation of vinyl amides to produce enantioenriched α‐arylbenzamides is reported. The use of a chiral bisimidazoline (BIm) ligand, in combination with diethoxymethylsilane and aryl halides, enables the regioselective introduction of aryl groups to the internal position of the olefin, forging a new stereogenic center α to the N atom. The use of neutral reagents

  据报道，镍催化乙烯基酰胺的不对称还原氢化芳基化反应产生对映体富集的α-芳基苯甲酰胺。手性双咪唑啉（BIm）配体与二乙氧基甲基硅烷和芳基卤化物结合使用，可以将芳基区域选择性地引入烯烃的内部位置，从而将新的立体中心α锻造到N原子上。使用中性试剂和温和的反应条件可轻松获得抗癌药，SARS-CoV PLpro抑制剂和KCNQ通道开放剂中存在的与药理相关的基序。
• Eluent Tolerance and Enantioseparation Recovery of Chiral Packing Materials Based on Chitosan Bis(Phenylcarbamate)-(n-Octyl Urea)s for High Performance Liquid Chromatography
  作者：Jing Wang、Shao-Hua Huang、Wei Chen、Zheng-Wu Bai

  DOI：10.3390/molecules21111528

  日期：——

  capacity of the chitosan bis(phenylcarbamate)-(n-octyl urea)s in ethyl acetate, acetone and tetrahydrofuran (THF) was evaluated. Among the chitosan derivatives, the chitosan bis(3,5-dichlorophenylcarbamate)-(n-octyl urea) polymer showed the highest swelling capacity in ethyl acetate and THF. The polymer-based CSPs could be utilized with pure ethyl acetate and a normal phase containing 70% THF, but was

  本工作的目的是研究壳聚糖衍生物的溶胀对对映体分离的影响以及基于这些衍生物的手性固定相（CSP）的分离性能的恢复。因此，合成了六种壳聚糖双（苯基氨基甲酸酯）-（正辛基脲），将其包被在大孔3-氨基丙基硅胶上，得到了新的CSP。大多数CSP对测试的手性化合物表现出很强的对映体分离能力。评价了壳聚糖双（苯基氨基甲酸酯）-（正辛基脲）在乙酸乙酯，丙酮和四氢呋喃（THF）中的溶胀能力。在壳聚糖衍生物中，壳聚糖双（3,5-二氯苯基氨基甲酸酯）-（正辛基脲）聚合物在乙酸乙酯和THF中显示出最高的溶胀能力。基于聚合物的CSP可以与纯乙酸乙酯和含有70％THF的正相一起使用，但会被纯THF破坏。另一方面，损坏的CSP静置一段时间后可以恢复其分离性能。这些观察对于基于多糖衍生物的CSP的开发和应用是重要的。
• Chiral self-discrimination of the enantiomers of α-phenylethylamine derivatives in proton NMR
  作者：Shao-Hua Huang、Zheng-Wu Bai、Ji-Wen Feng

  DOI：10.1002/mrc.2406

  日期：2009.5

  of chiral analytes, the urea and amide derivatives of α‐phenylethylamine, were prepared. The effect of inter‐molecular hydrogen‐bonding interaction on self‐discrimination of the enantiomers of analytes has been investigated using high‐resolution 1H NMR. It was found that the urea derivatives with double‐hydrogen‐bonding interaction exhibit not only the stronger hydrogen‐bonding interaction but also better

  制备了两种手性分析物，即 α-苯乙胺的尿素和酰胺衍生物。已使用高分辨率 1H NMR 研究了分子间氢键相互作用对分析物对映体自识别的影响。发现具有双氢键相互作用的脲衍生物不仅表现出更强的氢键相互作用，而且比酰胺衍生物（除了带有两个 NO2 基团的衍生物）具有更好的自识别能力。目前的结果表明，双氢键相互作用促进了手性化合物的自识别能力。版权所有 © 2009 John Wiley & Sons, Ltd.
• 3-Acyl-2-(N-cyanoimino)oxazolidine derivative, a new asymmetric acylating agent for racemic secondary alkyl amines
  作者：Naoyoshi Maezaki、Akemi Furusawa、Shuji Uchida、Tetsuaki Tanaka

  DOI：10.1016/s0040-4020(01)00933-4

  日期：2001.11

  A 3-acyl-2-(N-cyanoimino)oxazolidine derivative was found to serve as an enantioselective acylating agent for sec-alkyl amines. These reagents differentiate the enantiomers of 1-phenylethylamine derivatives up to 85% ee, and the recovered chiral auxiliary is reusable.

  发现3-酰基-2-（N-氰基氨基）恶唑烷衍生物用作仲烷基胺的对映选择性酰化剂。这些试剂可区分高达85％ee的1-苯基乙胺衍生物的对映异构体，并且回收的手性助剂可重复使用。
• 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.