(2R,3S)-2-fluoro-2-methyloctane-1,3-diol | 1052107-64-8

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 卤代醇
• 英文名称: (2R,3S)-2-fluoro-2-methyloctane-1,3-diol
• CAS: 1052107-64-8
• 化学式: C₉H₁₉FO₂
• 分子量: 178.247
• InChiKey: QEBVESLEIOZNEE-DTWKUNHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.65
• 重原子数：
  12.0
• 可旋转键数：
  6.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  40.46
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (2R,3S)-2-fluoro-2-methyloctane-1,3-diol 在 2,4,6-三甲基吡啶 作用下， 以 四氢呋喃 、 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 74.0h， 生成
  参考文献：
  名称：

  Titanium mediated asymmetric aldol reaction with α-fluoropropionimide enolates

  摘要：

  Aldol reaction utilising Evans N-(alpha-fluoropropyl)-2-oxazolidinones with TiCl4 have been explored. Reactions of N-(alpha-fluoropropyl)-2-oxazolidinones with aliphatic aldehydes generated (x-fluoro-p-hydroxy-aldol products with high diastereoselectivities. When (alpha R)- and (alpha S)-N-(alpha-fluoropropyl)-2-(4S)-oxazolidinones were explored as substrates they gave rise to identical aldol diastereoisomer products. Examination of the enolates formed in each case by F-19 NMR, after treatment with TiCl4, indicated that both preparations gave the same predominant enolate. This was assumed to be the E-enolate. The alpha-fluoro-beta-hydroxy-aldol products were removed from the auxiliary either by alcoholysis or reduction and converted to the corresponding alpha,beta-difluoro products by treatment with Deoxofluor (TM) (C) 2007 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2007.05.012
• 作为产物：
  描述：

  (4S)-3-((3S)-2-fluoro-3-hydroxy-2-methyloctanoyl)-4-isopropyloxazolidin-2-one 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 2.5h， 以66%的产率得到(2R,3S)-2-fluoro-2-methyloctane-1,3-diol
  参考文献：
  名称：

  Titanium mediated asymmetric aldol reaction with α-fluoropropionimide enolates

  摘要：

  Aldol reaction utilising Evans N-(alpha-fluoropropyl)-2-oxazolidinones with TiCl4 have been explored. Reactions of N-(alpha-fluoropropyl)-2-oxazolidinones with aliphatic aldehydes generated (x-fluoro-p-hydroxy-aldol products with high diastereoselectivities. When (alpha R)- and (alpha S)-N-(alpha-fluoropropyl)-2-(4S)-oxazolidinones were explored as substrates they gave rise to identical aldol diastereoisomer products. Examination of the enolates formed in each case by F-19 NMR, after treatment with TiCl4, indicated that both preparations gave the same predominant enolate. This was assumed to be the E-enolate. The alpha-fluoro-beta-hydroxy-aldol products were removed from the auxiliary either by alcoholysis or reduction and converted to the corresponding alpha,beta-difluoro products by treatment with Deoxofluor (TM) (C) 2007 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2007.05.012