(R)-3-(m-trifluoromethylphenyl)-butan-2-one | 1016651-70-9

• 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)-3-(m-trifluoromethylphenyl)-butan-2-one
• 英文别名: (R)-3-(3-trifluoromethylphenyl)butan-2-one；(3R)-3-[3-(Trifluoromethyl)phenyl]-2-butanone；(3R)-3-[3-(trifluoromethyl)phenyl]butan-2-one
• CAS: 1016651-70-9
• 化学式: C₁₁H₁₁F₃O
• 分子量: 216.203
• InChiKey: XKKQWJXCTRARGJ-ZETCQYMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-<3-(trifluoromethyl)phenyl>-2-butanone 在 glucose-6-phosphate dehydrogenase 、 glucose-6-phosphate 、 phenylacetone monooxygenase 、 还原型辅酶II(NADPH)四钠盐 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 (R)-3-(m-trifluoromethylphenyl)-butan-2-one 、 (S)-1-(3-trifluoromethylphenyl)ethyl acetate
  参考文献：
  名称：

  Ionic liquids for enhancing the enantioselectivity of isolated BVMO-catalysed oxidations

  摘要：

  本研究首次报道了在离子液体存在下使用分离的耐热贝耶尔-维利格单氧合酶（苯丙酮单氧合酶，PAMO）的情况。研究了不同离子液体存在下，PAMO作为氧化酶的稳定性、活性和选择性。结果显示，添加某些特定离子液体，如Ammoeng™ 102和[bmim]MeSO4，可以显著提高消旋苯甲酮氧化反应的E值。此外，离子液体的使用提高了进行贝耶尔-维利格氧化反应的最佳底物浓度，从而扩大了PAMO在合成应用中的生物催化范围。

  DOI：

  10.1039/c0gc00560f

文献信息

• BVMO-catalysed dynamic kinetic resolution of racemic benzyl ketones in the presence of anion exchange resins
  作者：Cristina Rodríguez、Gonzalo de Gonzalo、Ana Rioz-Martínez、Daniel E. Torres Pazmiño、Marco W. Fraaije、Vicente Gotor

  DOI：10.1039/b922693a

  日期：——

  fluorescens ACB was employed in the presence of a weak anion exchange resin to perform dynamic kinetic resolutions of racemic benzyl ketones with high conversions and good optical purities. Different parameters that affect to the efficiency of the enzymatic Baeyer–Villiger oxidation and racemisation were analyzed in order to optimize the activity and selectivity of the biocatalytic system.

  4-羟基苯乙酮来自荧光假单胞菌ACB的单加氧酶在弱阴离子交换树脂的存在下用于以高转化率和良好的光学纯度进行外消旋苄基酮的动态动力学拆分。为了优化生物催化系统的活性和选择性，分析了影响酶催化的拜耳-维利格氧化和外消旋化效率的不同参数。
• Selective Baeyer–Villiger oxidation of racemic ketones in aqueous–organic media catalyzed by phenylacetone monooxygenase
  作者：Cristina Rodríguez、Gonzalo de Gonzalo、Daniel E. Torres Pazmiño、Marco W. Fraaije、Vicente Gotor

  DOI：10.1016/j.tetasy.2007.12.008

  日期：2008.2

  enantioselective kinetic resolution of a set of racemic substituted 3-phenylbutan-2-ones employing phenylacetone monooxygenase (PAMO) in non-conventional media was performed. The studies have revealed the effects of a range of solvents on the biocatalytic properties of the biocatalyst. Also, the enzymatic oxidation of α-acetylphenylacetonitrile was performed using organic cosolvents. This has resulted in a dynamic

  使用苯丙酮单加氧酶（PAMO）在非常规介质中进行了一组外消旋取代的3-苯基丁烷-2-酮的对映选择性动力学拆分。研究已经揭示了多种溶剂对生物催化剂的生物催化性能的影响。另外，使用有机助溶剂进行α-乙酰基苯基乙腈的酶促氧化。这导致该氰酮的动态动力学拆分，产生对映纯（R）-2-乙酰氧基苯基乙腈，其产率取决于所采用的反应条件。
• Baeyer–Villiger monooxygenase-catalyzed kinetic resolution of racemic α-alkyl benzyl ketones: enzymatic synthesis of α-alkyl benzylketones and α-alkyl benzylesters
  作者：Cristina Rodríguez、Gonzalo de Gonzalo、Daniel E. Torres Pazmiño、Marco W. Fraaije、Vicente Gotor

  DOI：10.1016/j.tetasy.2009.03.018

  日期：2009.6

  The application of three BVMOs for the enantioselective oxidation of 3-phenylbutan-2-ones with different substituents in the aromatic moiety is described. By choosing the appropriate biocatalyst and substrate combination, chiral ketones and esters can be obtained with excellent enantiopurities. This methodology could also be applied to the resolution of racemic alpha-alkyl benzylketones with longer alkyl chains as well as with two substituted alpha-substituted benzylacetones. A kinetic analysis revealed that the BVMOs studied effectively convert all tested compounds showing that the enzymes are tolerant towards the substrate structure while being highly enantioselective. These properties render BVMOs as valuable biocatalysts for the preparation of compounds with high interest in organic synthesis. (C) 2009 Elsevier Ltd. All rights reserved.