(2S,3R)-2-(benzyloxycarbonylamino)-6,6,7,7,8,8,9,9,10,10,11,11,11-tridecafluoro-1-phenyl-undecan-3-ol | 871210-17-2

• 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: (2S,3R)-2-(benzyloxycarbonylamino)-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)-(benzyloxycarbonylamino)-6,6,7,7,8,8,9,9,10,10,11,11,11-tridecafluoro-1-phenyl-undecan-3-ol；benzyl N-[(2S,3R)-6,6,7,7,8,8,9,9,10,10,11,11,11-tridecafluoro-3-hydroxy-1-phenylundecan-2-yl]carbamate
• CAS: 871210-17-2
• 化学式: C₂₅H₂₂F₁₃NO₃
• 分子量: 631.434
• InChiKey: DHJQZGJZXGZEMT-ZWKOTPCHSA-N

物化性质

• 熔点：
  131-135 °C
• 沸点：
  520.2±50.0 °C(Predicted)
• 密度：
  1.415±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8
• 重原子数：
  42
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  (2S,3R)-2-(benzyloxycarbonylamino)-6,6,7,7,8,8,9,9,10,10,11,11,11-tridecafluoro-1-phenyl-undecan-3-ol 在 sodium hydride 、 盐酸 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 生成 4-苄基-5-(3,3,4,4,5,5,6,6,7,7,8,8,8-十三氟辛基)-1,3-恶唑烷-2-酮
  参考文献：
  名称：

  WO2006/96994

  摘要：

  公开号：
• 作为产物：
  描述：

  苄基(S)-1-(N-甲氧基-N-甲基氨基甲酰基)-2-苯乙基氨基甲酸酯 在 叔丁基锂 、 lithium tri-t-butoxyaluminum hydride 作用下， 以 乙醚 、 乙醇 、 正己烷 为溶剂， 生成 (2S,3R)-2-(benzyloxycarbonylamino)-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

• Fluorous Oxazolidinone Chiral Auxiliary Compounds and Methods of Manufacture
  申请人：Hultin Philip Gregory

  公开号：US20090018343A1

  公开（公告）日：2009-01-15

  The present invention relates generally to perfluoroalkyl chiral auxiliary compounds and methods of manufacture. These compounds have the functionality to effectively support the synthesis of chiral compounds in single reactions, high-throughput parallel reactions, or combinatorial reactions The invention relates to two oxazolidinone chiral auxiliaries (1) and (2): wherein R f is a perfluoroalkyl group having the general formula (CH 2 ) x —C y F 2y+1 where x=1-5 and y=4-10 and wherein B is an unfunctionalized aryl, alkyl or arylalkyl group in a preferred embodiment, x=2 and y=6 and B is derived from unfunctionalized amino acids The amino acids may be from either the D- or L-series, and are preferably enantiomerically pure or in very high enantiomeric excess in either configuration.

  本发明涉及全氟烷基手性辅助化合物及其制造方法。这些化合物具有有效支持手性化合物在单反应、高通量并行反应或组合反应中合成的功能。本发明涉及两种噁唑烷手性辅助剂（1）和（2）：其中Rf是具有一般式（CH2）x - CyF2y + 1的全氟烷基，其中x = 1-5，y = 4-10，B是非功能化芳基，烷基或芳基烷基组，在优选实施例中，x = 2，y = 6，B来源于非功能化氨基酸。氨基酸可以来自D-或L系列，并且最好在任何构型中具有对映纯或非常高的对映选择性。
• 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.