(R)-2′-(2-methoxyphenyl)-[1,1′-binaphthalen]-2-ol

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (R)-2′-(2-methoxyphenyl)-[1,1′-binaphthalen]-2-ol
• 英文别名: (R)-2-(2-methoxyphenyl)-1,1'-binaphthyl-2'-ol；1-[2-(2-Methoxyphenyl)naphthalen-1-yl]naphthalen-2-ol；1-[2-(2-methoxyphenyl)naphthalen-1-yl]naphthalen-2-ol
• 化学式: C₂₇H₂₀O₂
• 分子量: 376.455
• InChiKey: OUYSUJBMPYBWCM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  三氟甲磺酸酐 、 (R)-2′-(2-methoxyphenyl)-[1,1′-binaphthalen]-2-ol 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以85%的产率得到(R)-2-(2-methoxyphenyl)-1,1'-binaphthyl-2'-yl trifluoromethanesulfonate
  参考文献：
  名称：

  The development of an approach toward sterically-hindered chiral 2′-aryl-1,1′-binaphthalenes functionalized at position 2

  摘要：

  Several approaches were examined for the preparation of 1,1'-binaphthalene derivatives bearing sterically demanding ortho-substituted aryl at position 2' which are suitable for further functionalization at position 2. Steric hindrance of ortho-substituted aryl groups was critical for the approach through BINOL monotriflate. Among variations of cross-coupling reactions of 2,2'-dihalo-1,1'-binaphthalenes, Negishi arylation of an enantiopure 2,2'-dibromide was found to be the method of choice for regioselective and stereoconservative preparation of the target 2'-monoarylated precursor. Functionalization of the latter at position 2 was demonstrated by bromine substitution via lithiation followed by the reaction with several electrophiles. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.08.046
• 作为产物：
  描述：

  (R)-1,1'-Bi-2-naphthol 在 magnesium 、 N,N-二异丙基乙胺 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 11.73h， 生成 (R)-2′-(2-methoxyphenyl)-[1,1′-binaphthalen]-2-ol
  参考文献：
  名称：

  在温和条件下通过互补的镍催化的熊田偶联反应获得2'取代的联萘单醇：P，O配体的关键作用

  摘要：

  报道了两种互补的Kumada偶联方法，可在温和条件下将单三氟代1,1'-联萘-2,2'-二醇（BINOL）转化为2'-取代的联萘一元醇。使用NiCl 2（dppe）与改进的单三氟甲磺酸酯制备方法相结合，对于含有未取代或贫电子芳基或苄基2'取代基的1,1'-联萘-2-醇有效。对于含有新戊基或富含电子的芳基2'取代基的产品，使用可能具有半不稳定双齿次膦4醇配体的替代方法更为优越。所获得的联萘醇代表用于手性配体和助剂的潜在有用的合成子。

  DOI：

  10.1021/jo400349r

文献信息

• The development of an approach toward sterically-hindered chiral 2′-aryl-1,1′-binaphthalenes functionalized at position 2
  作者：Michaela Mešková、Martin Putala

  DOI：10.1016/j.tetlet.2011.08.046

  日期：2011.10

  Several approaches were examined for the preparation of 1,1'-binaphthalene derivatives bearing sterically demanding ortho-substituted aryl at position 2' which are suitable for further functionalization at position 2. Steric hindrance of ortho-substituted aryl groups was critical for the approach through BINOL monotriflate. Among variations of cross-coupling reactions of 2,2'-dihalo-1,1'-binaphthalenes, Negishi arylation of an enantiopure 2,2'-dibromide was found to be the method of choice for regioselective and stereoconservative preparation of the target 2'-monoarylated precursor. Functionalization of the latter at position 2 was demonstrated by bromine substitution via lithiation followed by the reaction with several electrophiles. (C) 2011 Elsevier Ltd. All rights reserved.
• Access to 2′-Substituted Binaphthyl Monoalcohols via Complementary Nickel-Catalyzed Kumada Coupling Reactions under Mild Conditions: Key Role of a P,O Ligand
  作者：Sachin Handa、Yohan L. N. Mathota Arachchige、LeGrande M. Slaughter

  DOI：10.1021/jo400349r

  日期：2013.6.7

  combination with an improved preparation of the monotriflate, is effective for 1,1′-binaphthalene-2-ols containing unsubstituted or electron-poor aryl or benzyl 2′-substituents. An alternative procedure, using a potentially hemilabile-bidentate phosphinan-4-ol ligand, is superior for products containing neopentyl or electron-rich aryl 2′-substituents. The obtained binaphthyl alcohols represent potentially

  报道了两种互补的Kumada偶联方法，可在温和条件下将单三氟代1,1'-联萘-2,2'-二醇（BINOL）转化为2'-取代的联萘一元醇。使用NiCl 2（dppe）与改进的单三氟甲磺酸酯制备方法相结合，对于含有未取代或贫电子芳基或苄基2'取代基的1,1'-联萘-2-醇有效。对于含有新戊基或富含电子的芳基2'取代基的产品，使用可能具有半不稳定双齿次膦4醇配体的替代方法更为优越。所获得的联萘醇代表用于手性配体和助剂的潜在有用的合成子。