(1R,2R,4S,6S)-2,6-O-[allylboryl]-2-(naphthalen-1-yl)bicyclo[2.2.2]octanediol | 1067234-29-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (1R,2R,4S,6S)-2,6-O-[allylboryl]-2-(naphthalen-1-yl)bicyclo[2.2.2]octanediol
• 英文别名: (1S,3R,7S,8R)-3-naphthalen-1-yl-5-prop-2-enyl-4,6-dioxa-5-boratricyclo[5.3.1.03,8]undecane
• CAS: 1067234-29-0
• 化学式: C₂₁H₂₃BO₂
• 分子量: 318.223
• InChiKey: OWYXXLYFYDLLSF-ZFCZOSEKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.94
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1R,2R,4S,6S)-2,6-O-[allylboryl]-2-(naphthalen-1-yl)bicyclo[2.2.2]octanediol 、 苯甲醛 在 scandium tris(trifluoromethanesulfonate) 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 (S)-1-苯基-3-丁烯-1-醇 、 (R)-1-Phenylbut-3-en-1-ol
  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：

  (1R,2R,4S,6S)-2-(naphthalen-1-yl)-bicyclo[2.2.2]octane-2,6-diol 、 烯丙基溴化镁 在 硼酸三乙酯 、 氯化铵 作用下， 以 乙醚 为溶剂， 反应 4.5h， 以63%的产率得到(1R,2R,4S,6S)-2,6-O-[allylboryl]-2-(naphthalen-1-yl)bicyclo[2.2.2]octanediol
  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