(1S,2S,4S,5S)-2-(naphthalen-1-yl)bicyclo[2.2.2]octane-2,5-diol | 1053243-54-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (1S,2S,4S,5S)-2-(naphthalen-1-yl)bicyclo[2.2.2]octane-2,5-diol
• CAS: 1053243-54-1
• 化学式: C₁₈H₂₀O₂
• 分子量: 268.356
• InChiKey: OBLWPDDIUQUGHW-USJZOSNVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.21
• 重原子数：
  20.0
• 可旋转键数：
  1.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.44
• 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：

  (1S,2S,4S,5S)-2-(naphthalen-1-yl)bicyclo[2.2.2]octane-2,5-diol 在 四丙基高钌酸铵 、 N-甲基吗啉氧化物 作用下， 以 二氯甲烷 为溶剂， 以92%的产率得到(1S,4S,5S)-5-hydroxy-5-(naphthalen-1-yl)bicyclo[2.2.2]octan-2-one
  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
• 作为产物：
  描述：

  1-溴代萘 、 (1S,4S,5S)-5-hydroxybicyclo<2.2.2>octan-2-one 以 四氢呋喃 、 乙醚 为溶剂， 以40%的产率得到(1S,2S,4S,5S)-2-(naphthalen-1-yl)bicyclo[2.2.2]octane-2,5-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