2(S)-(iso-propoxycarbonylamino)-3,3-bis(1'H,1'H,2'H,2'H-perfluorooctyl)-1-phenyl-propan-3-ol | 871210-09-2

• 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: 2(S)-(iso-propoxycarbonylamino)-3,3-bis(1'H,1'H,2'H,2'H-perfluorooctyl)-1-phenyl-propan-3-ol
• 英文别名: 2(S)-(isopropyloxycarbonylamino)-3,3-bis(1'H,1'H,2'H,2'H-perfluorooctyl)-1-phenyl-propan-3-ol；propan-2-yl N-[(2S)-6,6,7,7,8,8,9,9,10,10,11,11,11-tridecafluoro-3-hydroxy-1-phenyl-3-(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)undecan-2-yl]carbamate
• CAS: 871210-09-2
• 化学式: C₂₉H₂₅F₂₆NO₃
• 分子量: 929.481
• InChiKey: AAWDTCFRFGNZLF-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.3
• 重原子数：
  59
• 可旋转键数：
  20
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  29

反应信息

• 作为反应物：
  描述：

  2(S)-(iso-propoxycarbonylamino)-3,3-bis(1'H,1'H,2'H,2'H-perfluorooctyl)-1-phenyl-propan-3-ol 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 生成 4(S)-benzyl-5,5-bis(1'H,1'H,2'H,2'H-perfluorooctyl)-2-oxazolidinone
  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：

  L-苯丙氨酸甲酯盐酸盐 在 叔丁基锂 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 为溶剂， 反应 2.0h， 生成 2(S)-(iso-propoxycarbonylamino)-3,3-bis(1'H,1'H,2'H,2'H-perfluorooctyl)-1-phenyl-propan-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

• WO2006/96994
  申请人：——

  公开号：——

  公开（公告）日：——
• 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.