(4R)-(-)-5,5,5-trifluoro-4-[(1R)-2-hydroxy-1-phenylethylamino]pentan-2-one | 1044222-25-4

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (4R)-(-)-5,5,5-trifluoro-4-[(1R)-2-hydroxy-1-phenylethylamino]pentan-2-one
• 英文别名: (4R)-5,5,5-trifluoro-4-[[(1R)-2-hydroxy-1-phenylethyl]amino]pentan-2-one
• CAS: 1044222-25-4
• 化学式: C₁₃H₁₆F₃NO₂
• 分子量: 275.271
• InChiKey: URAZREFLHNZVBS-NWDGAFQWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (4R)-(-)-5,5,5-trifluoro-4-[(1R)-2-hydroxy-1-phenylethylamino]pentan-2-one 在 palladium hydroxide, 20 wt% on carbon 、 三氟化硼乙醚 、 氢气 、 magnesium sulfate 、 对甲苯磺酸 、 sodium hydroxide 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 水 、 甲苯 、 苯 为溶剂， 20.0~70.0 ℃ 、344.75 kPa 条件下， 反应 8.0h， 生成 (-)-3-[(2S,6R)-6-(trifluoromethyl)piperidin-2-yl]propanoic acid
  参考文献：
  名称：

  Asymmetric synthesis of trifluoromethyl-piperidine based γ-amino acids and of trifluoromethyl-indolizidines

  摘要：

  The asymmetric synthesis of trifluoromethyl-piperidine-based gamma-aminoacids and of indolizidines bearing a trifluoromethyl group is reported. These rarely described compounds are prepared in a highly enantio-enriched form employing as key step an intramolecular Mannich type process, involving an enantiopure Tfm-aminoketal and ethyl oxobutenoate as aldehyde partner. Used strategy together with obtained compounds allows the access to a wide range of Tfm-N-(poly)heterocycles, structures of obvious interest for the research of new bioactive drugs. (c) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2012.11.006
• 作为产物：
  描述：

  2-(三甲基硅氧基)丙烯 、 (4R)-2-三氟甲基-4-苯基-1,3-恶唑烷 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 以89%的产率得到(4R)-(-)-5,5,5-trifluoro-4-[(1R)-2-hydroxy-1-phenylethylamino]pentan-2-one
  参考文献：
  名称：

  (三氟甲基)哌啶的不对称合成：高度对映体富集的α'-(三氟甲基)哌啶酸的制备

  摘要：

  报道了（三氟甲基）哌啶酸的第一个不对称合成。合成策略涉及作为关键步骤的同手性 α-Tfm-β-氨基缩酮的分子内曼尼希反应，该反应通过四步从氟代半缩醛以高立体选择性制备。

  DOI：

  10.1055/s-2008-1072768

文献信息

• Asymmetric synthesis of trifluoromethyl-piperidine based γ-amino acids and of trifluoromethyl-indolizidines
  作者：Wahid Bux Jatoi、Agnès Desiront、Aurélie Job、Yves Troin、Jean-Louis Canet

  DOI：10.1016/j.jfluchem.2012.11.006

  日期：2013.1

  The asymmetric synthesis of trifluoromethyl-piperidine-based gamma-aminoacids and of indolizidines bearing a trifluoromethyl group is reported. These rarely described compounds are prepared in a highly enantio-enriched form employing as key step an intramolecular Mannich type process, involving an enantiopure Tfm-aminoketal and ethyl oxobutenoate as aldehyde partner. Used strategy together with obtained compounds allows the access to a wide range of Tfm-N-(poly)heterocycles, structures of obvious interest for the research of new bioactive drugs. (c) 2012 Elsevier B.V. All rights reserved.
• Asymmetric Synthesis of (Trifluoromethyl)piperidines: Preparation of Highly Enantioenriched α′-(Trifluoromethyl)pipecolic Acids
  作者：Jean-Louis Canet、Wahid Jatoi、Annabelle Bariau、Cécile Esparcieux、Gilles Figueredo、Yves Troin

  DOI：10.1055/s-2008-1072768

  日期：2008.5

  The first asymmetric synthesis of (trifluoromethyl)pipecolic acids is reported. The synthetic strategy involves as key step an intramolecular Mannich reaction of a homochiral α-Tfm-β-amino ketal, prepared with a high stereoselectively in four steps from a fluoral hemiacetal.

  报道了（三氟甲基）哌啶酸的第一个不对称合成。合成策略涉及作为关键步骤的同手性 α-Tfm-β-氨基缩酮的分子内曼尼希反应，该反应通过四步从氟代半缩醛以高立体选择性制备。