((3R,5R)-5-((R)-1-bromopropyl)-5-phenyltetrahydrofuran-3-yl)methanol | 1593266-14-8

• 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: ((3R,5R)-5-((R)-1-bromopropyl)-5-phenyltetrahydrofuran-3-yl)methanol
• 英文别名: [(3R,5R)-5-[(R)-bromo(phenyl)methyl]-5-phenyloxolan-3-yl]methanol
• CAS: 1593266-14-8
• 化学式: C₁₈H₁₉BrO₂
• 分子量: 347.252
• InChiKey: LOUFPLNUJLHCEO-ZTFGCOKTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  ((3R,5R)-5-((R)-1-bromopropyl)-5-phenyltetrahydrofuran-3-yl)methanol 、 3,5-二硝基苯甲酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以92%的产率得到[(3S,5R)-5-[(R)-bromo(phenyl)methyl]-5-phenyloxolan-3-yl]methyl 3,5-dinitrobenzoate
  参考文献：
  名称：

  Catalytic Asymmetric Bromoetherification and Desymmetrization of Olefinic 1,3-Diols with C₂-Symmetric Sulfides

  摘要：

  An enantioselective and highly diastereoselective bromoetherification and desymmetrization of olefinic 1,3-diols has been developed using a C-2-symmetric cyclic sulfide catalyst. This methodology has been successfully applied to the synthesis of the key intermediate of an orally active antifungal drug posaconazole (Noxafil).

  DOI：

  10.1021/ja5029155
• 作为产物：
  描述：

  在 N-溴代丁二酰亚胺(NBS) 、 甲烷磺酸 、 (3aS,4S,6S,6aS)-4,6-bis((4-(tert-butyl)phenoxy)methyl)-2,2-dimethyltetrahydrothieno[3,4-d][1,3]dioxole 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 以92%的产率得到((3R,5R)-5-((R)-1-bromopropyl)-5-phenyltetrahydrofuran-3-yl)methanol
  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