(3-Tert-butyl-2,5-dimethoxyphenyl)boronic acid | 1105008-67-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (3-Tert-butyl-2,5-dimethoxyphenyl)boronic acid
• 英文别名: (3-tert-butyl-2,5-dimethoxyphenyl)boronic acid
• CAS: 1105008-67-0
• 化学式: C₁₂H₁₉BO₄
• 分子量: 238.091
• InChiKey: JSNQWONXENMONG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.68
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  硼酸三甲酯 、 1-bromo-2,5-dimethoxy-3-tert-butylbenzene 在 正丁基锂 、 盐酸 作用下， 以 乙醚 、 正己烷 、 水 为溶剂， 反应 1.0h， 生成 (3-Tert-butyl-2,5-dimethoxyphenyl)boronic acid
  参考文献：
  名称：

  Influence of the Position of tert-Butyl Substituents on Reactivity of Quinone Dimers Yielding Dibenzofuran-1,4-diones

  摘要：

  Reactivity of two isomeric quinone dimers, 5,5'-di-tert-butyl-2,2'-bisbenzoquinone (2) and 6,6'-di-tert-butyl-2,2'-bisbenzoquinone (3) have been compared. Both quinone dimers underwent thermal cyclization in ethanol to give dibenzofuran-1,4-diones exclusively, the reaction proceeding faster for 3 than for 2. Molecular modeling analysis indicates that the different reactivity should be explained in terms of the steric hindrance of tert-butyl group in 2, which prevents approaching of solvent molecules to C=O moiety so that the solvent-assisted proton transfer occurs more slowly.

  DOI：

  10.3987/com-08-s(n)101
• 作为试剂：
  描述：

  1-bromo-2,5-dimethoxy-3-tert-butylbenzene 在 正丁基锂 、 (3-Tert-butyl-2,5-dimethoxyphenyl)boronic acid 作用下， 以 乙醚 、 正己烷 为溶剂， 反应 1.0h， 以78%的产率得到3,3'-di-tert-butyl-2,2',5,5'-tetramethoxybiphenyl
  参考文献：
  名称：

  Influence of the Position of tert-Butyl Substituents on Reactivity of Quinone Dimers Yielding Dibenzofuran-1,4-diones

  摘要：

  Reactivity of two isomeric quinone dimers, 5,5'-di-tert-butyl-2,2'-bisbenzoquinone (2) and 6,6'-di-tert-butyl-2,2'-bisbenzoquinone (3) have been compared. Both quinone dimers underwent thermal cyclization in ethanol to give dibenzofuran-1,4-diones exclusively, the reaction proceeding faster for 3 than for 2. Molecular modeling analysis indicates that the different reactivity should be explained in terms of the steric hindrance of tert-butyl group in 2, which prevents approaching of solvent molecules to C=O moiety so that the solvent-assisted proton transfer occurs more slowly.

  DOI：

  10.3987/com-08-s(n)101

文献信息

• Influence of the Position of tert-Butyl Substituents on Reactivity of Quinone Dimers Yielding Dibenzofuran-1,4-diones
  作者：Naoto Hayashi、Akifumi Kanda、Hiroyuki Higuchi、Keiko Ninomiya

  DOI：10.3987/com-08-s(n)101

  日期：——

  Reactivity of two isomeric quinone dimers, 5,5'-di-tert-butyl-2,2'-bisbenzoquinone (2) and 6,6'-di-tert-butyl-2,2'-bisbenzoquinone (3) have been compared. Both quinone dimers underwent thermal cyclization in ethanol to give dibenzofuran-1,4-diones exclusively, the reaction proceeding faster for 3 than for 2. Molecular modeling analysis indicates that the different reactivity should be explained in terms of the steric hindrance of tert-butyl group in 2, which prevents approaching of solvent molecules to C=O moiety so that the solvent-assisted proton transfer occurs more slowly.