2-methoxy-N-((R)-1-(4-(trifluoromethyl)phenyl)ethyl)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-methoxy-N-((R)-1-(4-(trifluoromethyl)phenyl)ethyl)acetamide
• 英文别名: (R)-2-methoxy-N-(1-(4-(trifluoromethyl)phenyl)ethyl)acetamide；2-methoxy-N-[(1R)-1-[4-(trifluoromethyl)phenyl]ethyl]acetamide
• 化学式: C₁₂H₁₄F₃NO₂
• 分子量: 261.244
• InChiKey: IEGRUHKWCSEVHG-MRVPVSSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  甲氧基乙酸甲酯 、 (Rs)-1-[4-(三氟甲基)苯基]乙胺 在 sodium carbonate 作用下， 以 甲苯 为溶剂， 反应 6.0h， 以99%的产率得到2-methoxy-N-((R)-1-(4-(trifluoromethyl)phenyl)ethyl)acetamide
  参考文献：
  名称：

  Fast racemization and dynamic kinetic resolution of primary benzyl amines

  摘要：

  We prepared a Pd nanocatalyst (average diameter of Pd nanoparticles = 1.73 nm) displaying a remarkable activity for the racemization and dynamic kinetic resolution (DKR) of 1-methylbenzylamine. It was eight times more active than the previous best. The DKR of 1-methylbenzylamine with the Pd nanocatalyst (2 mol %) in the presence of a thermostable lipase (Novozym 435) was complete in 6 h at 70 degrees C. The DKRs of other benzyl amines also proceeded to completion in 6 h under similar conditions except the amount of Pd nanocatalyst. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.08.050

文献信息

• Dynamic Kinetic Resolution of Primary Amines with a Recyclable Pd Nanocatalyst for Racemization
  作者：Mahn-Joo Kim、Won-Hee Kim、Kiwon Han、Yoon Kyung Choi、Jaiwook Park

  DOI：10.1021/ol070130d

  日期：2007.3.1

  A practical procedure for the dynamic kinetic resolution (DKR) of primary amines has been developed. This procedure employs a palladium nanocatalyst as the racemization catalyst, a commercial lipase (Novozym-435) as the resolution catalyst, and ethyl acetate or ethyl methoxyacetate as the acyl donor. Eleven primary amines and one amino acid amide have been efficiently resolved with good yields (85-99%)

  已经开发了伯胺动态动力学拆分（DKR）的实用程序。该方法采用钯纳米催化剂作为消旋催化剂，商业脂肪酶（Novozym-435）作为拆分催化剂，乙酸乙酯或甲氧基乙酸乙酯作为酰基供体。11种伯胺和一种氨基酸酰胺已得到有效拆分，收率良好（85-99％），对映体过量也很高（97-99％）。[反应：看文字]
• Chemoenzymatic Dynamic Kinetic Resolution of Primary Amines Using a Recyclable Palladium Nanoparticle Catalyst Together with Lipases
  作者：Karl P. J. Gustafson、Richard Lihammar、Oscar Verho、Karin Engström、Jan-E. Bäckvall

  DOI：10.1021/jo500508p

  日期：2014.5.2

  amines to DKR reactions using two commercially available lipases, Novozyme-435 (Candida antartica Lipase B) and Amano Lipase PS-C1 (lipase from Burkholderia cepacia) as biocatalysts. The latter enzyme has not previously been used in the DKR of amines because of its low stability at temperatures over 60 °C. The viability of the heterogeneous Pd-AmP-MCF was further demonstrated in a recycling study,

  将由载于氨基官能化硅质介孔泡沫（Pd-AmP-MCF）上的钯纳米粒子组成的催化剂用于化学酶动力学动力学拆分（DKR），可将伯胺高产率转化为酰胺。纳米催化剂在低于70°C的温度下的效率可实现更适合于酶的反应条件。在本研究中，这可以通过使用两种市售脂肪酶Novozyme-435（南极假丝酵母脂肪酶B）和Amano脂肪酶PS-C1（洋葱伯克霍尔德氏菌的脂肪酶）对1-苯基乙胺（1a）和类似的苄基胺进行DKR反应来举例说明。）作为生物催化剂。后者的酶以前在胺的DKR中尚未使用，因为它在60°C以上的温度下稳定性低。回收研究进一步证明了非均相Pd-AmP-MCF的可行性，该研究表明该催化剂最多可重复使用5次。
• Artificial plant cell walls as multi-catalyst systems for enzymatic cooperative asymmetric catalysis in non-aqueous media
  作者：Luca Deiana、Abdolrahim A. Rafi、Veluru Ramesh Naidu、Cheuk-Wai Tai、Jan-E. Bäckvall、Armando Córdova

  DOI：10.1039/d1cc02878b

  日期：——

  cellulose-based artificial plant cell wall (APCW) structures that contain different types of catalysts is a powerful strategy for the development of cascade reactions. Here we disclose an APCW catalytic system containing a lipase enzyme and nanopalladium particles that transform a racemic amine into the corresponding enantiomerically pure amide in high yield via a dynamic kinetic resolution.

  包含不同类型催化剂的纤维素基人造植物细胞壁 (APCW) 结构的组装是开发级联反应的有力策略。在这里，我们公开了一种包含脂肪酶和纳米钯颗粒的 APCW 催化系统，该系统通过动态动力学拆分将外消旋胺以高产率转化为相应的对映体纯酰胺。
• Asymmetric Reductive Acylation of Aromatic Ketoximes by Enzyme-Metal Cocatalysis
  作者：Kiwon Han、Jaiwook Park、Mahn-Joo Kim

  DOI：10.1021/jo800270n

  日期：2008.6.1

  We have developed an efficient procedure for the asymmetric synthesis of chiral amides from ketoximes. This one-pot procedure employs two different types of catalysts, Pd nanocatalyst and lipase, for three consecutive transformations including hydrogenation, racemization, and acylation. Eight ketoximes have been efficiently transformed to the corresponding amides in good yields (83-92%) and high enantiomeric excesses (93-98%).
• Method for Preparing Optically Active Amines
  申请人：Kim Mahn-Joo

  公开号：US20090035830A1

  公开（公告）日：2009-02-05

  The present invention relates to a method of preparing optically active amines and chiral amines prepared thereby. The method includes reacting an amine compound, a metal catalyst, a biocatalyst including a lipase, and an acyl donor compound in an organic solvent to obtain a chiral amide compound, and then hydrolyzing the chiral amide compound to obtain a chiral amine.