3-(6-Trimethylsilanyl-1-vinylidene-hex-5-ynyl)-oxazolidin-2-one | 292072-30-1

• 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: 3-(6-Trimethylsilanyl-1-vinylidene-hex-5-ynyl)-oxazolidin-2-one
• CAS: 292072-30-1
• 化学式: C₁₄H₂₁NO₂Si
• 分子量: 263.412
• InChiKey: ARFWISJUBLBFKQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.16
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 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：

  3-(6-Trimethylsilanyl-1-vinylidene-hex-5-ynyl)-oxazolidin-2-one 在 potassium carbonate 作用下， 以 甲醇 、 二甲基亚砜 、 甲苯 为溶剂， 生成 3-(2-Oxo-3,5,6,7-tetrahydro-2H-inden-4-yl)-oxazolidin-2-one
  参考文献：
  名称：

  The First Regioselective α-Deprotonation and Functionalization of Allenamides. An Application in Intramolecular Pauson−Khand-Type Cycloadditions

  摘要：

  The first regioselective alpha-deprotonation and functionalization of electron-deficient allenamines are described here. The acidities of alpha- and gamma-allenic protons of these allenamides are readily differentiated using strong bases, thereby allowing regioselective substitutions at either the alpha- or gamma-allenic position, A specific synthetic application of the novel alpha-substituted allenamides in intramolecular Pauson-Khand-type cycloadditions is also described here.

  DOI：

  10.1021/ol000181+
• 作为产物：
  描述：

  5-iodo-1-trimethylsilyl-1-pentyne 、 3-(1,2-丙二烯)-(9ci)-2-噁唑烷酮 在 六甲基磷酰三胺 、 正丁基锂 作用下， 以 various solvent(s) 为溶剂， 以57%的产率得到3-(6-Trimethylsilanyl-1-vinylidene-hex-5-ynyl)-oxazolidin-2-one
  参考文献：
  名称：

  The First Regioselective α-Deprotonation and Functionalization of Allenamides. An Application in Intramolecular Pauson−Khand-Type Cycloadditions

  摘要：

  The first regioselective alpha-deprotonation and functionalization of electron-deficient allenamines are described here. The acidities of alpha- and gamma-allenic protons of these allenamides are readily differentiated using strong bases, thereby allowing regioselective substitutions at either the alpha- or gamma-allenic position, A specific synthetic application of the novel alpha-substituted allenamides in intramolecular Pauson-Khand-type cycloadditions is also described here.

  DOI：

  10.1021/ol000181+