2-ethoxy-N-(1-phenylethyl)acetamide

• 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-ethoxy-N-(1-phenylethyl)acetamide
• 化学式: C₁₂H₁₇NO₂
• mdl: MFCD03929256
• 分子量: 207.272
• InChiKey: CYARCJXEYMDZGC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.416
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-乙氧基乙酸乙酯 、 α-苯乙胺 以 甲苯 为溶剂， 反应 1.0h， 生成 2-ethoxy-N-(1-phenylethyl)acetamide
  参考文献：
  名称：

  Isopropyl 2-ethoxyacetate—an efficient acylating agent for lipase-catalyzed kinetic resolution of amines in batch and continuous-flow modes

  摘要：

  Productivity [conversion (c) and specific reaction rate (r(batch) or r(flow))] and enantiomer selectivity [enantiomeric ratio (E) and enantiomeric excess (ee) of the products] of ethyl and isopropyl esters of acetic, 2-methoxyacetic and 2-ethoxyacetic acids as acylating agents were compared in the N-acylation of (+/-)-1-phenylethanamine rac-1 catalyzed by variously immobilized forms of Candida antarctica lipase B (CaLB) using shake flasks and continuous-flow reactors. The effect of the temperature in the 0-80 degrees C range on productivity and enantiomer selectivity in KRs of rac-1 was investigated with the isopropyl esters in continuous-flow mode using CaLB-filled minireactors. Isopropyl 2-ethoxyacetate surpassed the performance of ethyl 2-methoxyacetate in terms of both productivity (1.9-2.9 times higher rate in batch mode) and enantiomeric selectivity (ee((R)-amide)>99.9% compared to 99.8%) providing at 40 degrees C high volumetric productivity (2.22 kg L-1 h(-1)), specific reaction rate and enantiomeric excess (r(flow)=783 mu mol min(-1) g(-1), ee((R)),e((R)-2c)>99.9%). (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.12.046

文献信息

• Chemoenzymatic Dynamic Kinetic Resolution of Amines in Fully Continuous-Flow Mode
  作者：Emese Farkas、Márk Oláh、Attila Földi、János Kóti、János Éles、József Nagy、Cristian Andrei Gal、Csaba Paizs、Gábor Hornyánszky、László Poppe

  DOI：10.1021/acs.orglett.8b03676

  日期：2018.12.21

  In this study, lipase-mediated dynamic kinetic resolution (DKR) of various benzylic amines (1a–g) is presented which is realized in a so far unprecedented fully continuous-flow system. The DKR process applying sol–gel immobilized lipase B from Candida antarctica as biocatalyst, palladium on 3-aminopropyl-functionalized silica as racemization catalyst, isopropyl 2-ethoxyacetate as acylating agent, ammonium

  在这项研究中，提出了脂肪酶介导的各种苄基胺（1a – g）的动态动力学拆分（DKR），这是迄今为止前所未有的完全连续流动的系统所实现的。DKR工艺采用南极假丝酵母的溶胶-凝胶固定化脂肪酶B作为生物催化剂，3-氨基丙基官能化二氧化硅上的钯作为外消旋催化剂，2-乙氧基乙酸异丙酯作为酰化剂，甲酸铵作为氢和氮源，以及2-甲基-2在调节的压力下，以-丁醇为溶剂，以中等至良好的收率提供了所需的产物，并具有优异的对映体过量。
• Isopropyl 2-ethoxyacetate—an efficient acylating agent for lipase-catalyzed kinetic resolution of amines in batch and continuous-flow modes
  作者：Márk Oláh、Zoltán Boros、Gábor Hornyánszky、László Poppe

  DOI：10.1016/j.tet.2015.12.046

  日期：2016.11

  Productivity [conversion (c) and specific reaction rate (r(batch) or r(flow))] and enantiomer selectivity [enantiomeric ratio (E) and enantiomeric excess (ee) of the products] of ethyl and isopropyl esters of acetic, 2-methoxyacetic and 2-ethoxyacetic acids as acylating agents were compared in the N-acylation of (+/-)-1-phenylethanamine rac-1 catalyzed by variously immobilized forms of Candida antarctica lipase B (CaLB) using shake flasks and continuous-flow reactors. The effect of the temperature in the 0-80 degrees C range on productivity and enantiomer selectivity in KRs of rac-1 was investigated with the isopropyl esters in continuous-flow mode using CaLB-filled minireactors. Isopropyl 2-ethoxyacetate surpassed the performance of ethyl 2-methoxyacetate in terms of both productivity (1.9-2.9 times higher rate in batch mode) and enantiomeric selectivity (ee((R)-amide)>99.9% compared to 99.8%) providing at 40 degrees C high volumetric productivity (2.22 kg L-1 h(-1)), specific reaction rate and enantiomeric excess (r(flow)=783 mu mol min(-1) g(-1), ee((R)),e((R)-2c)>99.9%). (C) 2015 Elsevier Ltd. All rights reserved.