(E)-(4S,5R)-4-benzyl-3-(2'-butenoyl)-5-(1'H,1'H,2'H,2'H-perfluorooctyl)-2-oxazolidinone | 857637-81-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (E)-(4S,5R)-4-benzyl-3-(2'-butenoyl)-5-(1'H,1'H,2'H,2'H-perfluorooctyl)-2-oxazolidinone
• 英文别名: (4S,5R)-4-benzyl-3-[(E)-but-2-enoyl]-5-(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)-1,3-oxazolidin-2-one
• CAS: 857637-81-1
• 化学式: C₂₂H₁₈F₁₃NO₃
• 分子量: 591.369
• InChiKey: BITURGCJJOXJEQ-QVBXTRIASA-N

物化性质

• 沸点：
  425.6±55.0 °C(Predicted)
• 密度：
  1.438±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  39
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  (E)-(4S,5R)-4-benzyl-3-(2'-butenoyl)-5-(1'H,1'H,2'H,2'H-perfluorooctyl)-2-oxazolidinone 在 氧气 lithium hydroxide 、 三乙基硼 、 双氧水 、 三正丁基氢锡 、 ytterbium(III) triflate 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 3.0h， 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：

  Stereoselective Conjugate Radical Additions:  Application of a Fluorous Oxazolidinone Chiral Auxiliary for Efficient Tin Removal

  摘要：

  A series of asymmetric free-radical-mediated intermolecular conjugate additions using a fluorous oxazolidinone chiral auxiliary has been completed. The fluorous auxiliary facilitated product isolation using fluorous solid phase extractions (FSPE), effectively removing excess organic and organometallic reagents. Parallel reactions carried out with a similar but nonfluorous norephedrine-derived oxazoldinone demonstrated the superior stereoselectivity and purification obtainable with the fluorous chiral auxiliary.

  DOI：

  10.1021/ol050956k
• 作为产物：
  描述：

  N-乙氧羰基-L-苯丙氨酸 在 sodium hydride 、 lithium tri-t-butoxyaluminum hydride 、 N,N-二异丙基乙胺 、 异戊酰氯 、 lithium chloride 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 生成 (E)-(4S,5R)-4-benzyl-3-(2'-butenoyl)-5-(1'H,1'H,2'H,2'H-perfluorooctyl)-2-oxazolidinone
  参考文献：
  名称：

  Stereoselective Conjugate Radical Additions:  Application of a Fluorous Oxazolidinone Chiral Auxiliary for Efficient Tin Removal

  摘要：

  A series of asymmetric free-radical-mediated intermolecular conjugate additions using a fluorous oxazolidinone chiral auxiliary has been completed. The fluorous auxiliary facilitated product isolation using fluorous solid phase extractions (FSPE), effectively removing excess organic and organometallic reagents. Parallel reactions carried out with a similar but nonfluorous norephedrine-derived oxazoldinone demonstrated the superior stereoselectivity and purification obtainable with the fluorous chiral auxiliary.

  DOI：

  10.1021/ol050956k

文献信息

• Recyclable supports for stereoselective 1,3-dipolar cycloadditions: application of a fluorous oxazolidinone chiral auxiliary
  作者：Jason E. Hein、Philip G. Hultin

  DOI：10.1016/j.tetasy.2005.05.041

  日期：2005.7

  The utility of a new fluorous-supported chiral auxiliary was tested using a series of catalyzed and uncatalyzed 1,3-dipolar cycloaddition reactions with diphenylnitrone. The yields and selectivities of the cycloadducts compare favourably with those obtained using the conventional Evans-type auxiliaries, while purification was greatly assisted by using fluorous solid phase extraction. Following characterization, the cycloadducts were released from the auxiliaries by reductive cleavage. The auxiliary was readily refunctionalized and reused in subsequent cycloaddition reactions, with no deterioration of the observed yields or selectivities. (c) 2005 Elsevier Ltd. All rights reserved.
• Stereoselective Conjugate Radical Additions:  Application of a Fluorous Oxazolidinone Chiral Auxiliary for Efficient Tin Removal
  作者：Jason E. Hein、Jake Zimmerman、Mukund P. Sibi、Philip G. Hultin

  DOI：10.1021/ol050956k

  日期：2005.6.1

  A series of asymmetric free-radical-mediated intermolecular conjugate additions using a fluorous oxazolidinone chiral auxiliary has been completed. The fluorous auxiliary facilitated product isolation using fluorous solid phase extractions (FSPE), effectively removing excess organic and organometallic reagents. Parallel reactions carried out with a similar but nonfluorous norephedrine-derived oxazoldinone demonstrated the superior stereoselectivity and purification obtainable with the fluorous chiral auxiliary.