(1R)-1-(3-oxo-1-cyclohexen-1-yl)butyl 2,2,4,4-tetramethyl-1,3-oxazolidine-3-carboxylate | 397300-19-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R)-1-(3-oxo-1-cyclohexen-1-yl)butyl 2,2,4,4-tetramethyl-1,3-oxazolidine-3-carboxylate
• 英文别名: [(1R)-1-(3-oxocyclohexen-1-yl)butyl] 2,2,4,4-tetramethyl-1,3-oxazolidine-3-carboxylate
• CAS: 397300-19-5
• 化学式: C₁₈H₂₉NO₄
• 分子量: 323.433
• InChiKey: TZESJXCQDVQOBS-OAHLLOKOSA-N

物化性质

• 沸点：
  420.5±45.0 °C(Predicted)
• 密度：
  1.067±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1R)-1-(3-oxo-1-cyclohexen-1-yl)butyl 2,2,4,4-tetramethyl-1,3-oxazolidine-3-carboxylate 在 甲烷磺酸 、 barium dihydroxide 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以61%的产率得到4-[(1R)-1-hydroxybutyl]-2-cyclohexen-1-one
  参考文献：
  名称：

  The Preparation of Nonracemic Secondary α-(Carbamoyloxy)alkylzinc and Copper Reagents. A Versatile Approach to Enantioenriched Alcohols

  摘要：

  GRAPHICSChiral alpha-(carbamoyloxy)alkyllithium reagents, prepared using Hoppe's sBuLi/(-)-sparteine methodology, were transmetalated with ZnCl2. Further transmetalation with CuCN with overall retention of configuration gave chiral species that reacted with various electrophiles to give enantiomerically pure alcohols after deprotection. A short, highly efficient synthesis of an industrially relevant pheromone, japonilure, illustrates the value of the methodology.

  DOI：

  10.1021/ol016986e
• 作为产物：
  描述：

  3-Iodocyclohex-2-enone 、 butyl 2,2,4,4-tetramethyl-1,3-oxazolidine-3-carboxylate 在 仲丁基锂 、 zinc(II) chloride 、 鹰爪豆碱 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 为溶剂， 反应 1.75h， 以42%的产率得到(1R)-1-(3-oxo-1-cyclohexen-1-yl)butyl 2,2,4,4-tetramethyl-1,3-oxazolidine-3-carboxylate
  参考文献：
  名称：

  The Preparation of Nonracemic Secondary α-(Carbamoyloxy)alkylzinc and Copper Reagents. A Versatile Approach to Enantioenriched Alcohols

  摘要：

  GRAPHICSChiral alpha-(carbamoyloxy)alkyllithium reagents, prepared using Hoppe's sBuLi/(-)-sparteine methodology, were transmetalated with ZnCl2. Further transmetalation with CuCN with overall retention of configuration gave chiral species that reacted with various electrophiles to give enantiomerically pure alcohols after deprotection. A short, highly efficient synthesis of an industrially relevant pheromone, japonilure, illustrates the value of the methodology.

  DOI：

  10.1021/ol016986e