(S)-4,4,4-Trifluoro-3-hydroxy-butyric acid isopropyl ester | 444579-14-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: (S)-4,4,4-Trifluoro-3-hydroxy-butyric acid isopropyl ester
• 英文别名: Butanoic acid, 4,4,4-trifluoro-3-hydroxy-, 1-methylethyl ester, (3S)-；propan-2-yl (3S)-4,4,4-trifluoro-3-hydroxybutanoate
• CAS: 444579-14-0
• 化学式: C₇H₁₁F₃O₃
• 分子量: 200.158
• InChiKey: QESVONPBAOMUNG-YFKPBYRVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4,4,4-三氟乙酰乙酸异丙酯 在 diiodo(p-cymene)ruthenium(II) dimer 氢气 作用下， 以 异丙醇 为溶剂， 77.0 ℃ 、2.0 MPa 条件下， 反应 16.0h， 生成 (R)-4,4,4-Trifluoro-3-hydroxy-butyric acid isopropyl ester 、 (S)-4,4,4-Trifluoro-3-hydroxy-butyric acid isopropyl ester
  参考文献：
  名称：

  用于Rh和Ru催化的对映选择性氢化的新型一类基于二茂铁基-芳基的二膦配体

  摘要：

  以四个步骤的顺序合成了一系列均基于苯基二茂铁基乙基骨架的新型Walphos配体家族的二膦。在铑或钌催化的烯烃和酮的不对称氢化中，对映选择性分别达到了95％和97％。将具有工业价值的2-异丙基肉桂酸衍生物在95％ee中进行氢化，其周转数> 5000。

  DOI：

  10.1002/adsc.200390003

文献信息

• A Novel Class of Ferrocenyl-Aryl-Based Diphosphine Ligands for Rh- and Ru-Catalysed Enantioselective Hydrogenation
  作者：Thomas Sturm、Walter Weissensteiner、Felix Spindler

  DOI：10.1002/adsc.200390003

  日期：2003.1

  A series of diphosphines of the novel Walphos ligand family all based on a phenylferrocenylethyl backbone were synthesised in a four-step sequence. In the rhodium- or ruthenium-catalysed asymmetric hydrogenation of olefins and ketones enantioselectivities of up to 95% and 97%, respectively, were obtained. A 2-isopropylcinnamic acid derivative of industrial interest was hydrogenated in 95% ee and with

  以四个步骤的顺序合成了一系列均基于苯基二茂铁基乙基骨架的新型Walphos配体家族的二膦。在铑或钌催化的烯烃和酮的不对称氢化中，对映选择性分别达到了95％和97％。将具有工业价值的2-异丙基肉桂酸衍生物在95％ee中进行氢化，其周转数> 5000。
• Modular chiral ligands: the profiling of the Mandyphos and Taniaphos ligand families
  作者：Felix Spindler、Christophe Malan、Matthias Lotz、Martin Kesselgruber、Ulrich Pittelkow、Andreas Rivas-Nass、Oliver Briel、Hans-Ulrich Blaser

  DOI：10.1016/j.tetasy.2004.06.033

  日期：2004.7

  A set of 11 ferrocenyl based diphosphine ligands (eight Mandyphos and three Taniaphos) was tested in more than 150 experiments using 20 test reactions. For the assessment of new ligands, a two-pronged strategy was developed consisting of a basic and an extended profiling. The basic profiling showed that the choice of the substituents at the P atoms has a significant effect on the catalyst performance. In the extended profiling it was confirmed that the Mandyphos ligands, in particular M4 with two bis(3,5-dimethyl-4-methoxyphenyl)phosphino groups, and the Taniaphos ligands, especially the all-phenyl derivative T1, showed good to outstanding performances in the hydrogenation of selected alpha- and beta-enamides, acrylic acid derivatives, itaconates, beta-ketoesters and 1,3-diketones yielding the corresponding products with up to 99% ee and at substrate/catalyst ratios up to 25,000. (C) 2004 Elsevier Ltd. All rights reserved.