(3S,4S)-2-benzyl-3-(tert-butyl)-4-hydroxymethylisoxazoline

• 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: (3S,4S)-2-benzyl-3-(tert-butyl)-4-hydroxymethylisoxazoline
• 英文别名: [(3S,4S)-2-benzyl-3-tert-butyl-1,2-oxazolidin-4-yl]methanol
• 化学式: C₁₅H₂₃NO₂
• 分子量: 249.353
• InChiKey: YQOFMLJYYYHACX-KBPBESRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  32.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-苄基羟胺 在 bis[(S)-BINOL/Ti(IV)] 作用下， 以 二氯甲烷 为溶剂， 反应 14.5h， 生成 (3S,4S)-2-benzyl-3-(tert-butyl)-4-hydroxymethylisoxazoline
  参考文献：
  名称：

  Asymmetric 1,3-Dipolar Cycloaddition Reaction of Nitrones and Acrolein with a Bis-Titanium Catalyst as Chiral Lewis Acid

  摘要：

  A mu-oxo-type chiral bis-Ti(IV) oxide (S,S)-1 can be successfully utilized in the asymmetric 1,3-dipolar cycloaddition reactions between various nitrones 2 and acrolein to give the corresponding isoxazolidines with high to excellent enantioselectivities. For instance, the reaction between nitrone 2 (R = t-Bu) and acrolein in the presence of 10 mol % of bis-Ti(IV) catalyst (S,S)-1 in dichloromethane at -40 degrees C gave the corresponding endo cycloadduct with 97% ee.

  DOI：

  10.1021/ja0523284

文献信息

• Asymmetric 1,3-Dipolar Cycloaddition Reaction of Nitrones and Acrolein with a Bis-Titanium Catalyst as Chiral Lewis Acid
  作者：Taichi Kano、Takuya Hashimoto、Keiji Maruoka

  DOI：10.1021/ja0523284

  日期：2005.8.1

  A mu-oxo-type chiral bis-Ti(IV) oxide (S,S)-1 can be successfully utilized in the asymmetric 1,3-dipolar cycloaddition reactions between various nitrones 2 and acrolein to give the corresponding isoxazolidines with high to excellent enantioselectivities. For instance, the reaction between nitrone 2 (R = t-Bu) and acrolein in the presence of 10 mol % of bis-Ti(IV) catalyst (S,S)-1 in dichloromethane at -40 degrees C gave the corresponding endo cycloadduct with 97% ee.