3-bromo-4-methoxyphenylboronic acid

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-bromo-4-methoxyphenylboronic acid
• 英文别名: 3-Bromo-4-methoxyphenylboronic acid；(3-bromo-4-methoxyphenyl)boronic acid
• 化学式: C₇H₈BBrO₃
• 分子量: 230.854
• InChiKey: LTFQTEKWUJUYEN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.14
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-bromo-4-methoxyphenylboronic acid 在 溶剂黄146 作用下， 以 1,4-二氧六环 为溶剂， 反应 24.0h， 以0.10 g的产率得到2-溴苯甲醚
  参考文献：
  名称：

  Metal-Free Protodeboronation of Electron-Rich Arene Boronic Acids and Its Application to ortho-Functionalization of Electron-Rich Arenes Using a Boronic Acid as a Blocking Group

  摘要：

  The metal-free thermal protodeboronation of various electron-rich arene boronic acids was studied. Several reaction parameters controlling this protodeboronation, such as solvent, temperature, and a proton source, have been investigated. On the basis of these studies, suitable reaction conditions for protodeboronation of several types of electron-rich arene boronic acids were provided. On the basis of this protodeboronation, a new protocol for the synthesis of ortho-functionalized electron-rich arenes from these boronic acids was developed using the boronic acid moiety as a blocking group in the electrophilic aromatic substitution reaction, followed by the removal of the boronic acid moiety via thermal protodeboronation. Mechanistic studies suggested that this protodeboronation might proceed via the complex formation of a boronic acid with a proton source, followed by the carbon-boron bond fission through σ-bond metathesis, to afford the corresponding arene compound and boric acid.

  DOI：

  10.1021/jo500780b
• 作为产物：
  描述：

  2-(3-bromo-4-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 在 三氯化硼 作用下， 以 二氯甲烷 为溶剂， 以98%的产率得到3-bromo-4-methoxyphenylboronic acid
  参考文献：
  名称：

  全合成阿凡韦洛尔

  摘要：

  报道了海洋天然产物阿夫那韦尔的首次全合成。总合成的特征是将甲苯磺酰和硼酸的无过渡金属的偶联首次用于制备复杂的天然产物，以及该偶联与受阻二邻位取代substrate底物的偶联的第一个实例。

  DOI：

  10.1021/acs.joc.7b02028

文献信息

• Metal-Free Protodeboronation of Electron-Rich Arene Boronic Acids and Its Application to <i>ortho</i>-Functionalization of Electron-Rich Arenes Using a Boronic Acid as a Blocking Group
  作者：Su-Jin Ahn、Chun-Young Lee、Nak-Kyoon Kim、Cheol-Hong Cheon

  DOI：10.1021/jo500780b

  日期：2014.8.15

  The metal-free thermal protodeboronation of various electron-rich arene boronic acids was studied. Several reaction parameters controlling this protodeboronation, such as solvent, temperature, and a proton source, have been investigated. On the basis of these studies, suitable reaction conditions for protodeboronation of several types of electron-rich arene boronic acids were provided. On the basis of this protodeboronation, a new protocol for the synthesis of ortho-functionalized electron-rich arenes from these boronic acids was developed using the boronic acid moiety as a blocking group in the electrophilic aromatic substitution reaction, followed by the removal of the boronic acid moiety via thermal protodeboronation. Mechanistic studies suggested that this protodeboronation might proceed via the complex formation of a boronic acid with a proton source, followed by the carbon-boron bond fission through σ-bond metathesis, to afford the corresponding arene compound and boric acid.
• Total Synthesis of Avrainvilleol
  作者：Aaron Wegener、Kenneth A. Miller

  DOI：10.1021/acs.joc.7b02028

  日期：2017.11.3

  The first total synthesis of the marine natural product avrainvilleol is reported. The total synthesis features the first application of the transition-metal-free coupling of a tosyl hydrazone and a boronic acid to the preparation of a complex natural product, and the first example of this coupling with a hindered diortho substituted hydrazone substrate.

  报道了海洋天然产物阿夫那韦尔的首次全合成。总合成的特征是将甲苯磺酰和硼酸的无过渡金属的偶联首次用于制备复杂的天然产物，以及该偶联与受阻二邻位取代substrate底物的偶联的第一个实例。