6-hydroxy-1,6-diphenylhexan-1-one | 58308-10-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-hydroxy-1,6-diphenylhexan-1-one
• CAS: 58308-10-4
• 化学式: C₁₈H₂₀O₂
• 分子量: 268.356
• InChiKey: JTOGZJOHQLMKJF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-hydroxy-1,6-diphenylhexan-1-one 在 异丙基氯化镁 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 38.58h， 生成 (S)-6-(4-methoxyphenyl)-1,6-diphenylhexan-1-one
  参考文献：
  名称：

  Nickel/Bis(oxazoline)-Catalyzed Asymmetric Negishi Arylations of Racemic Secondary Benzylic Electrophiles to Generate Enantioenriched 1,1-Diarylalkanes

  摘要：

  A tertiary stereogenic center that bears two different aryl substituents is found in a variety of bioactive compounds, including medicines such as Zoloft and Detrol. We have developed an efficient method for the synthesis of enantioenriched 1,1-diarylalkanes from readily available racemic benzylic alcohols. Formation of a benzylic mesylate (which is not isolated), followed by treatment with an arylzinc reagent, LiI, and a chiral nickel/bis(oxazoline) catalyst, furnishes the Negishi cross-coupling product in high ee and good yield. A wide array of functional groups (e.g., an aryl iodide, a thiophene, and an N-Boc-indole) are compatible with the mild reaction conditions. This method has been applied to a gram-scale synthesis of a precursor to Zoloft.

  DOI：

  10.1021/ja408561b