(1R,2R,4S,6S)-2-(naphthalen-1-yl)-bicyclo[2.2.2]octane-2,6-diol | 1067234-11-0

• 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-(naphthalen-1-yl)-bicyclo[2.2.2]octane-2,6-diol
• 英文别名: (1R,2R,4S,6S)-2-naphthalen-1-ylbicyclo[2.2.2]octane-2,6-diol
• CAS: 1067234-11-0
• 化学式: C₁₈H₂₀O₂
• 分子量: 268.356
• InChiKey: JMCIIVASTWRGBP-LSZYVWPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1R,2R,4S,6S)-2-(naphthalen-1-yl)-bicyclo[2.2.2]octane-2,6-diol 在 dimethyl sulfide borane 作用下， 以 氘代甲苯 为溶剂， 生成
  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 、 (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84%的产率得到(1R,2R,4S,6S)-2-(naphthalen-1-yl)-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

文献信息

• New bicyclic γ- and δ-aminoalcohols as catalysts for the asymmetric diethylzinc addition to benzaldehyde
  作者：Cecilia Olsson、Sara Helgesson、Torbjörn Frejd

  DOI：10.1016/j.tetasy.2008.06.002

  日期：2008.6

  A new class of chiral non-racemic γ- and δ-amino alcohols based on bicyclo[2.2.1]heptane and bicyclo[2.2.2]octane have been synthesized and used as catalysts in the asymmetric diethylzinc addition to benzaldehyde.

  合成了一种基于双环[2.2.1]庚烷和双环[2.2.2]辛烷的新型手性非外消旋γ-和δ-氨基醇，并用作苯甲醛不对称二乙基锌的催化剂。