(E)-(4S,5R)-3-(3'-ethoxycarbonyl-2'-propenoyl)-4-methyl-5-phenyl-2-oxazolidinone | 857637-88-8

• 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)-3-(3'-ethoxycarbonyl-2'-propenoyl)-4-methyl-5-phenyl-2-oxazolidinone
• 英文别名: ethyl (E)-4-[(4S,5R)-4-methyl-2-oxo-5-phenyl-1,3-oxazolidin-3-yl]-4-oxobut-2-enoate
• CAS: 857637-88-8
• 化学式: C₁₆H₁₇NO₅
• 分子量: 303.315
• InChiKey: QSEPXSPRCUIGOV-PEQFHUMCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  72.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (E)-(4S,5R)-3-(3'-ethoxycarbonyl-2'-propenoyl)-4-methyl-5-phenyl-2-oxazolidinone 、 2-碘代丙烷 在 氧气 三乙基硼 、 三正丁基氢锡 、 ytterbium(III) triflate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 (3'R,4S,5R)-4-methyl-3-(3'-ethoxycarbonyl-4'-methyl-pentanoyl)-5-phenyl-2-oxazolidinone 、 (3'S,4S,5R)-4-methyl-3-(3'-ethoxycarbonyl-4'-methyl-pentanoyl)-5-phenyl-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
• 作为产物：
  描述：

  去甲麻黄碱 在 TEA 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 生成 (E)-(4S,5R)-3-(3'-ethoxycarbonyl-2'-propenoyl)-4-methyl-5-phenyl-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