(4-(methoxymethoxy)naphthalen-1-yl)boronic acid

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (4-(methoxymethoxy)naphthalen-1-yl)boronic acid
• 英文别名: [4-(methoxymethoxy)naphthalen-1-yl]boronic acid
• 化学式: C₁₂H₁₃BO₄
• 分子量: 232.044
• InChiKey: ODGFXLYJXCRCRP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4-(methoxymethoxy)naphthalen-1-yl)boronic acid 在 盐酸 、 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 甲醇 、 水 为溶剂， 反应 3.0h， 生成 4-(2-bromo-5-methoxyphenyl)naphthalen-1-ol
  参考文献：
  名称：

  Palladium-Catalyzed Dynamic Kinetic Asymmetric Transformation of Racemic Biaryls: Axial-to-Central Chirality Transfer

  摘要：

  The first dynamic kinetic asymmetric transformation of racemic biaryl substrates on the basis of axial-to-central chirality transfer has been realized. Chiral Pd-NHC complexes were found to catalyze the dynamic kinetic asymmetric spiroannulation of 4-(2-bromoaryl)-naphthalen-1-ols (or 2'-bromo-[1,1'-biphenyl]-4-ols) with internal alkynes, affording a series of enantioenriched spirocyclic products bearing an all-carbon quaternary stereocenter in good yields (up to 95%) with excellent enantioselectivities (up to 97% ee).

  DOI：

  10.1021/jacs.5b01285

文献信息

• Studies of Palladium-Catalyzed Cross-Coupling Reactions for Preparation of Highly Hindered Biaryls Relevant to the Korupensamine/Michellamine Problem
  作者：Thomas R. Hoye、Minzhang Chen

  DOI：10.1021/jo960882d

  日期：1996.1.1
• Palladium-Catalyzed Dynamic Kinetic Asymmetric Transformation of Racemic Biaryls: Axial-to-Central Chirality Transfer
  作者：Liu Yang、Huayu Zheng、Lei Luo、Jiang Nan、Jingjing Liu、Yaoyu Wang、Xinjun Luan

  DOI：10.1021/jacs.5b01285

  日期：2015.4.22

  The first dynamic kinetic asymmetric transformation of racemic biaryl substrates on the basis of axial-to-central chirality transfer has been realized. Chiral Pd-NHC complexes were found to catalyze the dynamic kinetic asymmetric spiroannulation of 4-(2-bromoaryl)-naphthalen-1-ols (or 2'-bromo-[1,1'-biphenyl]-4-ols) with internal alkynes, affording a series of enantioenriched spirocyclic products bearing an all-carbon quaternary stereocenter in good yields (up to 95%) with excellent enantioselectivities (up to 97% ee).