methyl 2-[(2-methylpropan-2-yl)oxycarbonyl(18O)oxy-phenylmethyl]prop-2-enoate | 1316313-17-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 2-[(2-methylpropan-2-yl)oxycarbonyl(18O)oxy-phenylmethyl]prop-2-enoate
• CAS: 1316313-17-3
• 化学式: C₁₆H₂₀O₅
• 分子量: 294.332
• InChiKey: DHPUQFWATOTGKT-ZWXVIAAOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 2-[(2-methylpropan-2-yl)oxycarbonyl(18O)oxy-phenylmethyl]prop-2-enoate 在 三乙烯二胺 、 水 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以90%的产率得到2-(羟基苯基甲基)-丙烯酸甲酯
  参考文献：
  名称：

  Lewis Base Catalyzed Enantioselective Allylic Hydroxylation of Morita–Baylis–Hillman Carbonates with Water

  摘要：

  A Lewis base catalyzed allylic hydroxylation of Morita-Baylis-Hillman (MBH) carbonates has been developed. Various chiral MBH alcohols can be synthesized in high yields (up to 99%) and excellent enantioselectivities (up to 94% ee). This is the first report using water as a nucleophile in asymmetric organocatalysis. The nucleophilic role of water has been verified using O-18-labeling experiments.

  DOI：

  10.1021/jo201096e
• 作为产物：
  描述：

  methyl 2-{[(tert-butoxycarbonyl)oxy](phenyl)methyl}acrylate 在 三乙烯二胺 、 重氧水 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 methyl 2-[(2-methylpropan-2-yl)oxycarbonyl(18O)oxy-phenylmethyl]prop-2-enoate
  参考文献：
  名称：

  Lewis Base Catalyzed Enantioselective Allylic Hydroxylation of Morita–Baylis–Hillman Carbonates with Water

  摘要：

  A Lewis base catalyzed allylic hydroxylation of Morita-Baylis-Hillman (MBH) carbonates has been developed. Various chiral MBH alcohols can be synthesized in high yields (up to 99%) and excellent enantioselectivities (up to 94% ee). This is the first report using water as a nucleophile in asymmetric organocatalysis. The nucleophilic role of water has been verified using O-18-labeling experiments.

  DOI：

  10.1021/jo201096e