(1R,2R,4S,6S)-2-(2-ethylphenyl)bicyclo[2.2.2]octane-2,6-diol | 1067234-14-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1R,2R,4S,6S)-2-(2-ethylphenyl)bicyclo[2.2.2]octane-2,6-diol
• CAS: 1067234-14-3
• 化学式: C₁₆H₂₂O₂
• 分子量: 246.349
• InChiKey: YVJCAFWNHCGLIO-MWNCTCPHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-溴乙苯 、 (1R,4S,6S)-bicyclo<2.2.2>octane-6-ol-2-one 以 四氢呋喃 、 乙醚 为溶剂， 反应 1.0h， 以89%的产率得到(1R,2R,4S,6S)-2-(2-ethylphenyl)bicyclo[2.2.2]octane-2,6-diol
  参考文献：
  名称：

  Bicyclo[2.2.2]octane-derived chiral ligands—synthesis and application of BODOLs in the asymmetric reduction of acetophenone with catecholborane

  摘要：

  An improved synthetic route to the bicyclo[2.2.2]octane-2,6-diol ligands (2,6-BODOLS) allowed an increased structural variation of the ligand side-arm. The addition of aromatic or vinylic Grignard reagents to hydroxyketone 1 was highly selective and ligands 3f-3I were isolated in 84-97% yield. The addition of alkyl Grignard reagents containing beta-hydrogens resulted in lower yields (13-71%) due to competing ketone reduction. A number of 2,5-BODOLs were synthesized using a similar methodology. The ligands, together with Ti(OiPr)(4), were tested in the asymmetric reduction of acetophenone with catecholborane (up to 98% ee). 1-Naphthyl-BODOL 3i was employed as an allylboration reagent to benzaldehyde together with Sc(OTf)(3), resulting in (1S)-1-phenyl-3-buten-1-ol in 80% ee. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.07.006