((3R,5R)-5-((R)-1-bromopropyl)-5-phenyltetrahydrofuran-3-yl)methanol | 1593266-13-7

• 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-[(1R)-1-bromopropyl]-5-phenyloxolan-3-yl]methanol
• CAS: 1593266-13-7
• 化学式: C₁₄H₁₉BrO₂
• 分子量: 299.208
• InChiKey: GSSSIMKFJWMGKM-MRVWCRGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (Z)-2-(2-phenylpent-2-en-1-yl)propane-1,3-diol 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 、 1,2-二溴乙烷 为溶剂， 反应 72.0h， 以81%的产率得到
  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

文献信息

• Catalytic Asymmetric Bromoetherification and Desymmetrization of Olefinic 1,3-Diols with <i>C</i>₂-Symmetric Sulfides
  作者：Zhihai Ke、Chong Kiat Tan、Feng Chen、Ying-Yeung Yeung

  DOI：10.1021/ja5029155

  日期：2014.4.16

  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).