(4S)-4-tert-butyl-3-(2-phenylethynyl)-1,3-oxazolidin-2-one | 1245720-48-2

• 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: (4S)-4-tert-butyl-3-(2-phenylethynyl)-1,3-oxazolidin-2-one
• CAS: 1245720-48-2
• 化学式: C₁₅H₁₇NO₂
• 分子量: 243.305
• InChiKey: FTUFWANESWWTGR-CYBMUJFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  肉桂醇 、 (4S)-4-tert-butyl-3-(2-phenylethynyl)-1,3-oxazolidin-2-one 在 zinc trifluoromethanesulfonate 、 三甲基乙酸 作用下， 以 1,2-二氯乙烷 、 甲苯 为溶剂， 反应 24.0h， 以79%的产率得到(S)-4-tert-butyl-3-((2S,3S)-2,3-diphenylpent-4-enoyl)oxazolidin-2-one
  参考文献：
  名称：

  Alkynes to (E)-enolates using tandem catalysis: stereoselective anti-aldol and syn-[3,3]-rearrangement reactions

  摘要：

  A new tandem catalysis strategy that transforms alkyne derivatives to (E)-enol-equivalents followed by stereoselective anti-selective aldol coupling or syn-selective [3,3]-rearrangement transformations is reported. The mechanism is thought to proceed through an interchanging series of Lewis acid and Bronsted acid catalyzed reactions via the intermediacy of a ketiminum ion species. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.05.045

文献信息

• Alkynes to (E)-enolates using tandem catalysis: stereoselective anti-aldol and syn-[3,3]-rearrangement reactions
  作者：Neil P. Grimster、Donna A.A. Wilton、Louis K.M. Chan、Christopher R.A. Godfrey、Clive Green、Dafydd R. Owen、Matthew J. Gaunt

  DOI：10.1016/j.tet.2010.05.045

  日期：2010.8

  A new tandem catalysis strategy that transforms alkyne derivatives to (E)-enol-equivalents followed by stereoselective anti-selective aldol coupling or syn-selective [3,3]-rearrangement transformations is reported. The mechanism is thought to proceed through an interchanging series of Lewis acid and Bronsted acid catalyzed reactions via the intermediacy of a ketiminum ion species. (C) 2010 Elsevier Ltd. All rights reserved.