(R)-N-(1-(3-bromophenyl)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: (R)-N-(1-(3-bromophenyl)ethyl)acetamide
• 英文别名: N-[(1R)-1-(3-bromophenyl)ethyl]acetamide
• 化学式: C₁₀H₁₂BrNO
• 分子量: 242.115
• InChiKey: GHEDNSLOXLEUKX-SSDOTTSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  13
• 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

反应信息

• 作为产物：
  描述：

  (R)-N-(1-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethyl)acetamide 在 N-溴代丁二酰亚胺(NBS) 、 copper(I) bromide 作用下， 以 乙腈 为溶剂， 反应 12.0h， 以91%的产率得到(R)-N-(1-(3-bromophenyl)ethyl)acetamide
  参考文献：
  名称：

  Chemoenzymatic synthesis of boron-containing chiral amines and amides

  摘要：

  The first application of lipases as catalysts to obtain optically active boron-containing amines and amides is described. We studied several reaction conditions to achieve the kinetic resolution of boron-containing amines via enantioselective acylation mediated by Candida antarctica lipase B (CAL-B). Excellent enantioselectivity (E>200) and high enantiomeric excess (up to >99%) of both the remaining amines and amides were obtained. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.09.011

文献信息

• Asymmetric Synthesis of Nonracemic Primary Amines via Spiroborate-Catalyzed Reduction of Pure (<i>E</i>)- and (<i>Z</i>)-<i>O</i>-Benzyloximes: Applications toward the Synthesis of Calcimimetic Agents
  作者：Wenhua Ou、Sandraliz Espinosa、Héctor J. Meléndez、Silvia M. Farré、Jaime L. Alvarez、Valerie Torres、Ileanne Martínez、Kiara M. Santiago、Margarita Ortiz-Marciales

  DOI：10.1021/jo400371x

  日期：2013.6.7

  Highly enantiopure (1-aryl)- and (1-naphthyl)-1-ethylamines were synthesized by the borane-mediated reduction of single-isomeric (E)- and (Z)-O-benzyloxime ethers using the stable spiroborate ester derived from (S)-diphenyl valinol and ethylene glycol as the chiral catalyst. Primary (R)-arylethylamines were prepared by the reduction of pure (Z)-ethanone oxime ethers in up to 99% ee using 15% of catalyst

  使用衍生自稳定的螺硼酸酯，通过硼烷介导的单一异构体 ( E )- 和 ( Z ) -O-苄基肟醚的还原，合成了高对映体纯的 (1-芳基)-和 (1-萘基)-1-乙胺( S )-二苯基缬氨醇和乙二醇作为手性催化剂。伯 ( R )-芳基乙胺是通过使用 15% 的催化剂将纯 ( Z )-乙酮肟醚还原至 99% ee来制备的。描述了使用对映纯(1-萘-1-基)乙胺作为手性前体合成新的和已知的拟钙剂类似物的两种方便且容易的方法。
• Transaminases Applied to the Synthesis of High Added-Value Enantiopure Amines
  作者：Caroline E. Paul、María Rodríguez-Mata、Eduardo Busto、Iván Lavandera、Vicente Gotor-Fernández、Vicente Gotor、Susana García-Cerrada、Javier Mendiola、Óscar de Frutos、Iván Collado

  DOI：10.1021/op4003104

  日期：2014.6.20

  stereoselective amination of (hetero)aromatic ketones using transaminases have been studied, such as temperature, pH, substrate concentration, cosolvent, and source and percentage of amino donor, to further optimize the production of enantiopure amines using both (S)- and (R)-selective biocatalysts from commercial suppliers. Interesting enantiopure amino building blocks have been obtained, overcoming some limitations

  研究了使用转氨酶影响（杂）芳族酮的立体选择性胺化的关键参数，例如温度，pH，底物浓度，助溶剂以及氨基供体的来源和百分比，以进一步优化同时使用这两种方法生产对映体纯胺的方法（S） -和（R）选择性生物催化剂来自商业供应商。已经获得了有趣的对映纯氨基结构单元，克服了传统化学合成方法的某些局限性。扩大代表性方法的规模，提供对映体纯形式的卤代和杂芳族胺，分离产率高。
• Practical by Ligand Design: A New Class of Monodentate Phosphoramidite Ligands for Rhodium-Catalyzed Enantioselective Hydrogenations
  作者：Baoguo Zhao、Zheng Wang、Kuiling Ding

  DOI：10.1002/adsc.200606013

  日期：2006.6

  new class of low-cost and easy-to-prepare monodentate phosphoramidite ligands (CydamPhos) has been developed from readily accessible and cheap trans-1,2-diaminocyclohexane as starting material through a three-step transformation. This type of ligands exhibited excellent enantioseletivities and high activities in rhodium(I)-catalyzed asymmetric hydrogenations of dehydro-α-amino acid methyl esters 9 (ee:

  新型的低成本，易于制备的单齿亚磷酰胺配体（CydamPhos）是通过三步转化，从易于获得且便宜的反式-1,2-二氨基环己烷为原料开发的。这种类型的配体在铑（I）催化的脱氢-α-氨基酸甲酯9（ee：96.2-99.8％）和乙酰胺11（91.8-98.8％）的不对称氢化中表现出优异的对映异构性和高活性。基于催化剂前体的分子结构，合理化配体在催化的对映选择性控制上表现出的显着的取代作用。
• Stereoselective amination of racemic sec-alcohols through sequential application of laccases and transaminases
  作者：Lía Martínez-Montero、Vicente Gotor、Vicente Gotor-Fernández、Iván Lavandera

  DOI：10.1039/c6gc01981a

  日期：——

  A one-pot/two-step chemoenzymatic sequential methodology has been developed for the selective amination of secondary alcohols by combining the laccase from Trametes versicolor/TEMPO catalytic system with the stereoselective action of transaminases.

  已开发出一种一锅法/两步法的化学酶串联方法，通过将来自Trametes versicolor的漆酶/TEMPO催化系统与转氨酶的立体选择性作用相结合，实现了对次级醇的选择性胺化。
• Development of a Continuous-Flow System for Asymmetric Hydrogenation Using Self-Supported Chiral Catalysts
  作者：Lei Shi、Xingwang Wang、Christian A. Sandoval、Zheng Wang、Hongji Li、Jiang Wu、Liting Yu、Kuiling Ding

  DOI：10.1002/chem.200900899

  日期：2009.9.28

  whereas appropriate substrate/catalyst matching was needed for optimum chiral induction. The former was recycled 10 times without loss in ee (95–96 %), although a drop in TOF of approximately 20 % per cycle was observed. The estimation of effective catalytic sites in self‐supported catalyst 4 e was also carried out by isolation and hydrogenation of catalyst–substrate complex, showing about 37 % of the

  通过简单地混合多主题基于MonoPhos的配体（3； MonoPhos =基于1,1'-bi-2-萘酚的手性单齿亚磷酰胺）和[Rh （鳕鱼）2 ] BF 4（鳕鱼=环辛-8,1,5-二烯）。这种自支撑策略允许简单有效地固定催化剂，而无需使用额外的载体，从而得到了特性良好的，不溶的（甲苯）聚合材料（4）。所得的自负载催化剂（4）对许多α-脱氢氨基酸（5）和2-芳基酰胺（7）的不对称氢化表现出出色的催化性能。）的对映体过量（ee）范围分别为94–98％和90–98％。4中的接头部分对反应性有显着影响，尽管对对映体选择性影响很小。在稳态条件下获得的反应曲线表明4 h和4 i具有最高的反应性（在2个大气压下的转换频率（TOF）= 95和97 h -1），而最佳的底物/催化剂匹配是必需的手性诱导。尽管观察到每个循环的TOF下降约20％，但前者可循环使用10次而不会损失ee（95-96％）。自负载催化剂4