(1R,2S)-2-fluorocyclohexanol | 918300-56-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,2S)-2-fluorocyclohexanol
• 英文别名: Cyclohexanol, 2-fluoro-, (1R,2S)-；(1R,2S)-2-fluorocyclohexan-1-ol
• CAS: 918300-56-8
• 化学式: C₆H₁₁FO
• 分子量: 118.151
• InChiKey: LMYKFDDTPIOYQV-NTSWFWBYSA-N

物化性质

• 沸点：
  167.1±33.0 °C(Predicted)
• 密度：
  1.04±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-氟-环己醇 在 Pt/Al₂O₃ jones' reagent 、 氢气 、 溶剂黄146 、 辛可尼丁 作用下， 以 四氢呋喃 、 丙酮 为溶剂， -0.15~23.85 ℃ 、4.0 MPa 条件下， 生成 (1R,2S)-2-fluorocyclohexanol
  参考文献：
  名称：

  Asymmetric hydrogenation of racemic 2-fluorocyclohexanone over cinchona modified Pt/Al2O3 catalyst

  摘要：

  The first example of enantioselective heterogeneous catalytic hydrogenation of an a-fluoro ketone is reported. The hydrogenation of racemic 2-fluorocyclohexanone over cinchonidine- or methoxycinchonidine-modified Pt/Al2O3 resulted in diastereoselective and enantioselective formation of the cis-(1R, 2S)-2-fluorocyclohexanol. Due to the preferential hydrogenation of the S enantiomer, the kinetic resolution of the substrate was possible; the unreacted R enantiomer was accumulated in the reaction mixture. Under our experimental conditions, high diastereoselectivities (up to 85%) and good enantioselectivities (up to 59%) were obtained, demonstrating that activation of a ketone by a single alpha fluorine atom is efficient for obtaining enantiodiscrimination in this heterogeneous catalytic system. (c) 2006 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.jcat.2006.09.006

文献信息

• Asymmetric hydrogenation of racemic 2-fluorocyclohexanone over cinchona modified Pt/Al2O3 catalyst
  作者：K SZORI、G SZOLLOSI、M BARTOK

  DOI：10.1016/j.jcat.2006.09.006

  日期：2006.12.10

  The first example of enantioselective heterogeneous catalytic hydrogenation of an a-fluoro ketone is reported. The hydrogenation of racemic 2-fluorocyclohexanone over cinchonidine- or methoxycinchonidine-modified Pt/Al2O3 resulted in diastereoselective and enantioselective formation of the cis-(1R, 2S)-2-fluorocyclohexanol. Due to the preferential hydrogenation of the S enantiomer, the kinetic resolution of the substrate was possible; the unreacted R enantiomer was accumulated in the reaction mixture. Under our experimental conditions, high diastereoselectivities (up to 85%) and good enantioselectivities (up to 59%) were obtained, demonstrating that activation of a ketone by a single alpha fluorine atom is efficient for obtaining enantiodiscrimination in this heterogeneous catalytic system. (c) 2006 Elsevier Inc. All rights reserved.