(R)-octan-2-yl trifluoroacetate | 87337-94-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (R)-octan-2-yl trifluoroacetate
• 英文别名: trifluoroacetic acid-((R)-1-methyl-heptyl ester)；Trifluoressigsaeure-((R)-1-methyl-heptylester)；[(2R)-octan-2-yl] 2,2,2-trifluoroacetate
• CAS: 87337-94-8；332-83-2；87337-93-7；99032-13-0
• 化学式: C₁₀H₁₇F₃O₂
• 分子量: 226.239
• InChiKey: OSUSEXASYGZJOJ-MRVPVSSYSA-N

物化性质

• 沸点：
  79.8-80.8 °C(Press: 20 Torr)
• 密度：
  1.001 g/cm3(Temp: 425 °C)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  15
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 海关编码：
  2915900090

反应信息

• 作为产物：
  描述：

  L-2-辛醇 、 三氟乙酸 生成 (R)-octan-2-yl trifluoroacetate
  参考文献：
  名称：

  Stereochemistry of Formation and Hydrolysis of Esters of Perfluoro Acids

  摘要：

  DOI：

  10.1021/ja01137a011

文献信息

• Utilising hardly-water soluble substrates as a second phase enables the straightforward synthesis of chiral alcohols
  作者：Christina Kohlmann、Nora Robertz、Susanne Leuchs、Lasse Greiner、Shukralla Na’amnieh

  DOI：10.1039/c1gc15823f

  日期：——

  So far, the alcohol dehydrogenase-catalysed conversion of longer chain aliphatic substrates has been challenging due to their low solubility in aqueous solution. However, by utilising the ketone directly as a second organic phase, the straightforward synthesis of long chain aliphatic chiral alcohols is enabled.

  到目前为止，由于长链脂肪族底物在水溶液中的溶解度较低，通过醇脱氢酶催化的转化一直颇具挑战性。然而，通过直接利用酮作为第二有机相，我们实现了长链脂肪族手性醇的直接合成。
• Screening, Molecular Cloning, and Biochemical Characterization of an Alcohol Dehydrogenase from<i>Pichia pastoris</i>Useful for the Kinetic Resolution of a Racemic β-Hydroxy-β-trifluoromethyl Ketone
  作者：Dalia Bulut、Nongnaphat Duangdee、Harald Gröger、Albrecht Berkessel、Werner Hummel

  DOI：10.1002/cbic.201600101

  日期：2016.7.15

  Find the needle in the haystack! A new alcohol dehydrogenase—PPADH from P. pastoris—was identified. It is able to distinguish between the two enantiomers of the racemic β‐hydroxy‐β‐trifluoromethyl ketone 1 by efficiently reducing the S form to the corresponding stereochemically uniform 1,3‐diol (S,S)‐2.

  在大海捞针中找针！鉴定了一种新的醇脱氢酶-来自巴斯德毕赤酵母的PPADH 。通过有效地将S形式还原为相应的立体化学均一的1,3-二醇（S，S）-2，能够区分外消旋β-羟基-β-三氟甲基酮1的两种对映异构体。
• Iridium-Catalyzed Enantioselective Hydrogenation of Alkenylboronic Esters
  作者：Adnan Ganić、Andreas Pfaltz

  DOI：10.1002/chem.201200246

  日期：2012.5.29

  iridium complex derived from a phosphino–imidazoline ligand is a highly efficient catalyst for the asymmetric hydrogenation of terminal vinyl boronic esters (see scheme). On the other hand, trisubstituted alkenyl‐boronates can be reduced with high activity and good to excellent enantioselectivity employing a pyridine–phosphinite ligand.

  选择合适的配体：从膦基-咪唑啉配体衍生的铱络合物是高效的末端乙烯基硼酸酯不对称加氢催化剂（请参见方案）。另一方面，使用吡啶-次亚膦酸酯配体可还原三取代的烯基硼酸酯，且活性高，对映选择性良好，甚至极好。
• Iridium-Catalyzed Asymmetric Hydrogenation with Simple Cyclohexane-Based P/S Ligands: <i>In Situ</i> HP-NMR and DFT Calculations for the Characterization of Reaction Intermediates
  作者：Carlota Borràs、Maria Biosca、Oscar Pàmies、Montserrat Diéguez

  DOI：10.1021/acs.organomet.5b00790

  日期：2015.11.9

  We report a reduced but structurally valuable phosphite/phosphinite-thioether ligand library for the Ir-hydrogenation of 40 minimally functionalized alkenes, including relevant examples with poorly coordinative groups. We found that enantiomeric excesses are mainly dependent on the substrate structure and on some ligand parameters (i.e., the type of thioether/phosphorus moieties and the configuration of the phosphite group), whereas the substituents of the biaryl phosphite moiety had little impact. By tuning the ligand parameters we were able to find highly selective catalysts for a range of substrates (ee's up to 99%). These phosphite/phosphinite-thioether ligands have a simple backbone and thus yield simple NMR spectra that reduce signal overlap and facilitate the identification of relevant intermediates. Therefore, by combining HP-NMR spectroscopy and theoretical studies, we were also able to identify the catalytically competent Ir-dihydride alkene species, which made it possible to explain the enantioselectivity obtained.