(1R,4R)-2-benzyl-5-phenylbicyclo[2.2.2]octa-2,5-diene | 1374793-38-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: (1R,4R)-2-benzyl-5-phenylbicyclo[2.2.2]octa-2,5-diene
• CAS: 1374793-38-0
• 化学式: C₂₁H₂₀
• 分子量: 272.39
• InChiKey: SWUUZOYJWOJCHG-RTBURBONSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  (1R,2S,3S,4R)-6-oxo-3-phenylbicyclo[2.2.2]octan-2-yl methanesulfonate 在 2,4,6-三甲基吡啶 、 正丁基锂 、 iron(III)-acetylacetonate 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 为溶剂， 反应 2.66h， 生成 (1R,4R)-2-benzyl-5-phenylbicyclo[2.2.2]octa-2,5-diene
  参考文献：
  名称：

  Scalable Synthesis of Enantiomerically Pure Bicyclo[2.2.2]octadiene Ligands

  摘要：

  An operationally simple and scalable synthesis of enantiomerically pure bicyclo[2.2.2]octadiene (bod*) ligands relying on an organocatalytic one-pot Michael addition-aldol reaction with cheap 2-cyclohexenone and phenylacetaldehyde is presented. The crystalline bicyclic product 4a (6-hydroxy-5-phenylbicyclo[2.2.2]octan-2-one) is transformed into phenylbicyclo[2.2.2]oct-5-en-2-one 2, a versatile starting material for the 2-step synthesis of both symmetrical, such as Hayashi's Ph-bod* ligand, as well as novel unsymmetrical chiral dienes.

  DOI：

  10.1021/jo3005638

文献信息

• Scalable Synthesis of Enantiomerically Pure Bicyclo[2.2.2]octadiene Ligands
  作者：Stefan Abele、Roman Inauen、Dirk Spielvogel、Christian Moessner

  DOI：10.1021/jo3005638

  日期：2012.5.18

  An operationally simple and scalable synthesis of enantiomerically pure bicyclo[2.2.2]octadiene (bod*) ligands relying on an organocatalytic one-pot Michael addition-aldol reaction with cheap 2-cyclohexenone and phenylacetaldehyde is presented. The crystalline bicyclic product 4a (6-hydroxy-5-phenylbicyclo[2.2.2]octan-2-one) is transformed into phenylbicyclo[2.2.2]oct-5-en-2-one 2, a versatile starting material for the 2-step synthesis of both symmetrical, such as Hayashi's Ph-bod* ligand, as well as novel unsymmetrical chiral dienes.