(R)-2-(1-(4-methoxyphenyl)propyl)naphthalene | 1424035-40-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (R)-2-(1-(4-methoxyphenyl)propyl)naphthalene
• CAS: 1424035-40-4
• 化学式: C₂₀H₂₀O
• 分子量: 276.378
• InChiKey: FBVPNOZKGSAHMD-HXUWFJFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.39
• 重原子数：
  21.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  9.23
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  1-(naphthalen-2-yl)propan-1-ol 在 异丙基氯化镁 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 38.58h， 生成 (R)-2-(1-(4-methoxyphenyl)propyl)naphthalene
  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

文献信息

• Nickel-Catalyzed Cross-Couplings of Benzylic Pivalates with Arylboroxines: Stereospecific Formation of Diarylalkanes and Triarylmethanes
  作者：Qi Zhou、Harathi D. Srinivas、Srimoyee Dasgupta、Mary P. Watson

  DOI：10.1021/ja312087x

  日期：2013.3.6

  We have developed a stereospecific nickel-catalyzed cross-coupling of benzylic pivalates with arylboroxines. The success of this reaction relies on the use of Ni(cod)(2) as the catalyst and NaOMe as a uniquely effective base. This reaction has broad scope with respect to the arylboroxine and benzylic pivalate, enabling the synthesis of a variety of diarylalkanes and triarylmethanes in good to excellent yields and ee's.