N-(1-苯基乙基)-乙酰胺 | 36065-27-7

• 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: N-(1-苯基乙基)-乙酰胺
• 中文别名: N-(1-苯乙基)乙酰胺
• 英文名称: N-α-phenylethylacetamide
• 英文别名: N-(1-phenylethyl)acetamide；DL-N-acetyl-α-methylbenzylamine
• CAS: 36065-27-7
• 化学式: C₁₀H₁₃NO
• mdl: MFCD00040690
• 分子量: 163.219
• InChiKey: PAVMRYVMZLANOQ-UHFFFAOYSA-N

物化性质

• 熔点：
  72-73 °C
• 沸点：
  175-180 °C
• 密度：
  1.007

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 危险性防范说明：
  P261,P280,P301+P312,P302+P352,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  室温且干燥

反应信息

• 作为反应物：
  描述：

  N-(1-苯基乙基)-乙酰胺 在 盐酸 作用下， 生成 4-(1-氨基-乙基)-苯磺酸酰胺
  参考文献：
  名称：

  Jensen; Schmith, Hoppe-Seyler's Zeitschrift fur Physiologische Chemie, 1944, vol. 280, p. 35,38

  摘要：

  DOI：
• 作为产物：
  描述：

  苯基三氟甲烷磺酸酯 在 1,1'-双(二苯基膦)二茂铁 、 Wilkinson's catalyst 、 tris(dibenzylideneacetone)dipalladium (0) 氢气 、 N,N-二异丙基乙胺 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 1.0h， 生成 N-(1-苯基乙基)-乙酰胺
  参考文献：
  名称：

  Fast and Regioselective Heck Couplings with N-Acyl-N-vinylamine Derivatives

  摘要：

  Highly regioselective Heck couplings of aryl triflates with N-acyl-N-vinylamines lacking an N-alkyl substituent were achieved with reaction times of approximately 1 h in yields ranging from 62 to 98% using 1.5 mol % of Pd-2(dba)(3), 3 mol % of DPPF, and diethylisopropylamine in dioxane. The efficiency of these cross-couplings were studied with several N-vinylamides and an example each of an N-vinylcarbamate and an N-vinylurea. The Heck coupling products easily underwent acidic hydrolysis to the corresponding aryl methyl ketone or in situ hydrogenation in the presence of (Ph3P)(3)RhCl under a hydrogen atmosphere to provide the N-acyl derivatives of pharmaceutically relevant benzylic amines. The coupling of a vinyl triflate and more interestingly a vinyl tosylate to N-vinyl acetamide was also studied affording a 2-acylamino-1,3-butadiene with the same high regioselectivity in preference for the alpha-isomer. This result suggests that Heck couplings of electron-rich alkenes with vinyl tosylates also follow a cationic pathway.

  DOI：

  10.1021/jo050669u

文献信息

• Reaction Pathway and Rate-Determining Step of the Schmidt Rearrangement/Fragmentation: A Kinetic Study
  作者：Ryo Akimoto、Takehiro Tokugawa、Yutaro Yamamoto、Hiroshi Yamataka

  DOI：10.1021/jo300419c

  日期：2012.4.20

  pre-equilibrium in the formation of iminodiazonium (ID) ion and that the N2 liberation from the ID ion is rate-determining. Under high azide concentration conditions, where the effective reactant is the ID ion, the reaction gave a linear Hammett plot with a ρ value of −0.50. The observed substituent effects on the rate and the product selectivity imply that path bifurcation on the way from the rate-determining

  三甲基叠氮化硅在90％（v / v）的TFA水溶液中将3-苯基-2-丁酮与取代的3-苯基-2-丁酮进行Schmidt重排，生成了两种类型的产物：碎片和重排，其比例取决于取代基：碎片越多，电子越多-供体取代基。通过固氮法进行的速率测量表明存在诱导期，并且拟一级反应速率常数显示出相对于叠氮化物浓度的饱和动力学。结果表明，反应通过预平衡进行，形成亚氨基重氮（ID）离子，并且N 2从ID离子的释放是决定速率的。在高叠氮化物浓度的条件下，其中有效反应物是ID离子，该反应给出了ρ值为-0.50的线性Hammett图。如先前的分子动力学模拟所示，观察到的取代基对速率和产物选择性的影响暗示着从速率确定TS到产物态的路径发生分支，类似于贝克曼重排/片段化反应。
• A Single Lipase-Catalysed One-Pot Protocol Combining Aminolysis Resolution and Aza-Michael Addition: An Easy and Efficient Way to Synthesise β-Amino Acid Esters
  作者：Fan Xu、Qiongsi Wu、Xiaoyang Chen、Xianfu Lin、Qi Wu

  DOI：10.1002/ejoc.201500760

  日期：2015.8

  was developed to obtain chiral β-amino acid esters with lipase B from Candida antarctica (CAL-B) as the only catalyst. This method is conducted under mild reaction conditions and is very easy to handle. After a series of detailed optimization studies, ten racemic aromatic or aliphatic amines were subjected to this one-pot procedure, and twelve chiral β-amino acid esters and ten chiral amides were successfully

  开发了一种结合 aza-Michael 加成和氨解拆分的新型一锅法，以来自南极念珠菌 (CAL-B) 的脂肪酶 B 作为唯一催化剂获得手性 β-氨基酸酯。该方法在温和的反应条件下进行，非常容易操作。经过一系列详细的优化研究，10 种外消旋芳香族或脂肪族胺经过此一锅法处理，成功合成了 12 种手性 β-氨基酸酯和 10 种手性酰胺，其 ee 值在理论产率下具有优异的值。放大程序也没有明显降低反应速率或对映选择性，这使得该方法适用于手性 β-氨基酸酯的大规模生产。
• Bifunctional Pincer Catalysts for Chemoselective Transfer Hydrogenation and Related Reactions
  作者：Shirel Cohen、Alexey N. Bilyachenko、Dmitri Gelman

  DOI：10.1002/ejic.201801486

  日期：2019.7.23

  remarkably different catalytic activity behavior, depending on the nature of the functional groups. Transfer hydrogenation of nitrobenzene with FA as a hydrogen source was probed using iridium complexes 3 or 4 as a catalyst. Under the same conditions, the analogous palladium complex was found to be useful for the selective amidation of aniline with light carboxylic acids.

  描述了以FA为氢源的硝基芳烃化学选择性转移加氢制苯胺的方法及相关工艺的比较研究；这些过程是由一系列在二级配位领域配备不同官能团的钳形催化剂催化的。在这项研究中使用了一些新的（4和5）以及先前报道的（1-3）双功能PC（sp 3）P钳形复合物家族。报道的化合物表现出显着不同的催化活性，具体取决于功能组的性质。使用铱配合物3或4探测了以FA为氢源的硝基苯的转移氢化作为催化剂。在相同条件下，发现类似的钯配合物可用于苯胺与轻羧酸的选择性酰胺化。
• H-β-zeolite catalyzed transamidation of carboxamides, phthalimide, formamides and thioamides with amines under neat conditions
  作者：Sadu Nageswara Rao、Darapaneni Chandra Mohan、Subbarayappa Adimurthy

  DOI：10.1039/c5ra16933j

  日期：——

  Efficient transamidation of unactivated carboxamides, phthalimides, formamides and thioamides with amines under solvent-free conditions using H-β-zeolite as a green and recyclable heterogeneous catalyst is described. Easy work up, high purity of the products, recyclability and environmentally-friendly nature of the catalyst are the attractive features of the present methodology. This is the first report

  描述了在无溶剂条件下使用H-β沸石作为绿色可循环使用的非均相催化剂，将未活化的羧酰胺，邻苯二甲酰亚胺，甲酰胺和硫代酰胺与胺进行有效的氨基转移。易于加工，产物的高纯度，催化剂的可回收性和对环境友好的性质是本方法的吸引人的特征。这是在异质条件下硫酰胺转氨作用的第一份报告。
• HEPATITIS C VIRUS INHIBITORS AND USES THEREOF IN PREPARATION OF DRUGS
  申请人：CHANGZHOU YINSHENG PHARMACEUTICAL CO., LTD.

  公开号：US20170253614A1

  公开（公告）日：2017-09-07

  A series of hepatitis C virus (HCV) inhibitors and compositions and applications thereof in the preparation of drugs for treating chronic HCV infection. Especially, a series of compounds that are used as NS5A inhibitors, and compositions and uses thereof in the preparations of drugs.

  一系列丙型肝炎病毒（HCV）抑制剂及其组合物，以及在制备用于治疗慢性HCV感染的药物时的应用。特别是一系列用作NS5A抑制剂的化合物，以及在药物制剂中的组合物和用途。