(4R)-4-[(4R,5R)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-1,3-dioxolan-4-yl]-2,2-dimethyl-1,3-dioxolane | 37106-18-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4R)-4-[(4R,5R)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-1,3-dioxolan-4-yl]-2,2-dimethyl-1,3-dioxolane
• CAS: 37106-18-6
• 化学式: C₁₃H₂₂O₆
• 分子量: 274.314
• InChiKey: QOGZKAWEVTUGNF-GWOFURMSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (4R)-4-[(4R,5R)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-1,3-dioxolan-4-yl]-2,2-dimethyl-1,3-dioxolane 在 吡啶 、 盐酸 、 potassium carbonate 作用下， 以 甲醇 为溶剂， 生成
  参考文献：
  名称：

  Catalytic and enantioselective bromoetherification of olefinic 1,3-diols: mechanistic insight

  摘要：

  How can high enantioselectivity be achieved when the racemic background reaction proceeds at a rate comparable to that of the catalytic asymmetric reaction? We attempted to rationalize this counterin-tuitive observation by studying the effect of (1) catalyst structure, (2) temperature and addition sequence of components, (3) catalyst loading, and (4) Bronsted acid additives. In the course of our investigation, it was found that increasing the amount of catalyst used led to inhibition of the stoichiometric reaction. Olefinic 1,3-diol 1, 5 mol % of catalyst 3a, 1 equiv of MsOH, and NBS were added at low temperature in a specific sequence to provide the best performance for the enantioselective bromoetherification. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.09.016