4-benzyl-2-(4-methoxyphenyl)oxazol-5-yl 1-phenylpropan-2-yl carbonate | 1017848-63-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-benzyl-2-(4-methoxyphenyl)oxazol-5-yl 1-phenylpropan-2-yl carbonate
• CAS: 1017848-63-3
• 化学式: C₂₇H₂₅NO₅
• 分子量: 443.499
• InChiKey: NCBHPWPLVBYKTI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.09
• 重原子数：
  33.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  70.79
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  4-benzyl-2-(4-methoxyphenyl)oxazol-5-yl 1-phenylpropan-2-yl carbonate 在 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 1.0h， 以60%的产率得到1-phenylpropan-2-yl 4-benzyl-2-(4-methoxyphenyl)-5-oxo-4,5-dihydrooxazole-4-carboxylate
  参考文献：
  名称：

  Probing the Efficiency of N-Heterocyclic Carbene Promoted O- to C-Carboxyl Transfer of Oxazolyl Carbonates

  摘要：

  Screening of a range of azolium salts, bases and solvents for reactivity indicates that triazolinylidenes, generated in situ with KHMDS in THF, promote the Steglich rearrangement of oxazolyl carbonates with high catalytic efficiency (typical reaction time 5 min at < 1.5 mol % NHC). This protocol shows wide substrate applicability, even allowing the efficient generation of vicinal quaternary centers. An improved experimental procedure is also described that allows a simplified one-pot reaction protocol to be employed with similarly high catalytic efficiency.

  DOI：

  10.1021/jo702720a
• 作为产物：
  描述：

  1-phenylpropan-2-yl chloroformate 、 4-benzyl-2-(4-methoxyphenyl)oxazol-5(4H)-one 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 以78%的产率得到4-benzyl-2-(4-methoxyphenyl)oxazol-5-yl 1-phenylpropan-2-yl carbonate
  参考文献：
  名称：

  Probing the Efficiency of N-Heterocyclic Carbene Promoted O- to C-Carboxyl Transfer of Oxazolyl Carbonates

  摘要：

  Screening of a range of azolium salts, bases and solvents for reactivity indicates that triazolinylidenes, generated in situ with KHMDS in THF, promote the Steglich rearrangement of oxazolyl carbonates with high catalytic efficiency (typical reaction time 5 min at < 1.5 mol % NHC). This protocol shows wide substrate applicability, even allowing the efficient generation of vicinal quaternary centers. An improved experimental procedure is also described that allows a simplified one-pot reaction protocol to be employed with similarly high catalytic efficiency.

  DOI：

  10.1021/jo702720a