(2S,3R)-2-amino-6,6,7,7,8,8,9,9,10,10,11,11,11-tridecafluoro-1-phenyl-undecan-3-ol | 871210-26-3

• 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: (2S,3R)-2-amino-6,6,7,7,8,8,9,9,10,10,11,11,11-tridecafluoro-1-phenyl-undecan-3-ol
• 英文别名: (2S,3R)-2-amino-6,6,7,7,8,8,9,9,10,10,11,11,11-tridecafluoro-1-phenylundecan-3-ol
• CAS: 871210-26-3
• 化学式: C₁₇H₁₆F₁₃NO
• 分子量: 497.299
• InChiKey: NOPGLRMHUKKOOA-WDEREUQCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  32
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  46.2
• 氢给体数：
  2
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  (2S,3R)-2-amino-6,6,7,7,8,8,9,9,10,10,11,11,11-tridecafluoro-1-phenyl-undecan-3-ol 、 二硫化碳 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 以80%的产率得到(4S,5R)-4-benzyl-5-(1'H,1'H,2'H,2'H-perfluorooctyl)-2-oxazolidinethione
  参考文献：
  名称：

  Practical Synthesis of Fluorous Oxazolidinone Chiral Auxiliaries from α-Amino Acids

  摘要：

  A series of new fluorous-supported oxazolidinone chiral auxiliaries has been prepared using a versatile and general five-step pathway, starting from readily available chiral a-amino acids. The key feature of this synthesis is the efficient generation of a suitably active perfluoroalkyllithium species. By use of this protocol, the auxiliaries can be obtained in high enantiomeric purity and on multigram scales from L-phenylalanine and L-valine with overall yields as high as 55%. The new methodology also incorporates fluorous solid-phase extraction on the large scale, allowing bulk quantities (up to 25 g) of fluorous compounds to be purified from the crude reaction mixture.

  DOI：

  10.1021/jo051696n
• 作为产物：
  描述：

  (S)-methyl 2-((ethoxycarbonyl)amino)-3-phenylpropanoate 在 氢氧化钾 、 magnesium 、 lithium tri-t-butoxyaluminum hydride 作用下， 以 乙醚 、 乙醇 、 乙酸乙酯 为溶剂， 反应 24.0h， 生成 (2S,3R)-2-amino-6,6,7,7,8,8,9,9,10,10,11,11,11-tridecafluoro-1-phenyl-undecan-3-ol
  参考文献：
  名称：

  Practical Synthesis of Fluorous Oxazolidinone Chiral Auxiliaries from α-Amino Acids

  摘要：

  A series of new fluorous-supported oxazolidinone chiral auxiliaries has been prepared using a versatile and general five-step pathway, starting from readily available chiral a-amino acids. The key feature of this synthesis is the efficient generation of a suitably active perfluoroalkyllithium species. By use of this protocol, the auxiliaries can be obtained in high enantiomeric purity and on multigram scales from L-phenylalanine and L-valine with overall yields as high as 55%. The new methodology also incorporates fluorous solid-phase extraction on the large scale, allowing bulk quantities (up to 25 g) of fluorous compounds to be purified from the crude reaction mixture.

  DOI：

  10.1021/jo051696n

文献信息

• Practical Synthesis of Fluorous Oxazolidinone Chiral Auxiliaries from α-Amino Acids
  作者：Jason E. Hein、Laina M. Geary、Ashley A. Jaworski、Philip G. Hultin

  DOI：10.1021/jo051696n

  日期：2005.11.1

  A series of new fluorous-supported oxazolidinone chiral auxiliaries has been prepared using a versatile and general five-step pathway, starting from readily available chiral a-amino acids. The key feature of this synthesis is the efficient generation of a suitably active perfluoroalkyllithium species. By use of this protocol, the auxiliaries can be obtained in high enantiomeric purity and on multigram scales from L-phenylalanine and L-valine with overall yields as high as 55%. The new methodology also incorporates fluorous solid-phase extraction on the large scale, allowing bulk quantities (up to 25 g) of fluorous compounds to be purified from the crude reaction mixture.