4-tert-butyl-2,5-dimethoxyphenylboronic acid | 1001438-02-3

• 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: 4-tert-butyl-2,5-dimethoxyphenylboronic acid
• 英文别名: (4-Tert-butyl-2,5-dimethoxyphenyl)boronic acid；(4-tert-butyl-2,5-dimethoxyphenyl)boronic acid
• CAS: 1001438-02-3
• 化学式: C₁₂H₁₉BO₄
• 分子量: 238.091
• InChiKey: KLJANJXBDGLIEJ-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

• 作为反应物：
  描述：

  4-tert-butyl-2,5-dimethoxyphenylboronic acid 在 双氧水 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以1.010 g的产率得到2,5-dimethoxy-4-^tbutylphenol
  参考文献：
  名称：

  β-丙氨酰氨基肽酶发色苯恶嗪酮底物的合成和测试。

  摘要：

  已合成新型7-N-（β-丙氨酰基）氨基苯恶嗪-3-酮盐27a-d并作为β-丙氨酰氨基肽酶的生色底物进行了测试，该酶存在于铜绿假单胞菌中，铜绿假单胞菌是囊性纤维化患者中最常见的呼吸道病原体。生物学结果表明，7-N-（β-丙氨酰基）氨基-1-戊基苯恶嗪-3-一三氟乙酸盐27a是该细菌的发色底物，在营养培养基中的扩散程度低，可用于细菌培养和明亮的培养。红色，使其很容易与琼脂背景区分开。

  DOI：

  10.1039/b716978g
• 作为产物：
  描述：

  1-bromo-4-tert-butyl-2,5-dimethoxybenzene 在 正丁基锂 、 硼酸三甲酯 、 盐酸 作用下， 以 乙醚 、 正己烷 为溶剂， 反应 2.0h， 以79%的产率得到4-tert-butyl-2,5-dimethoxyphenylboronic acid
  参考文献：
  名称：

  Synthesis, Structure, and Properties of Benzoquinone Dimer and Trimers Bearing t-Bu Substituents

  摘要：

  Highly soluble and stable quinone dimer and trimers were successfully yielded by introduction of t-Bu substituents. In X-ray structure analysis, the dimer quinone moiety was distorted into the boat shape, which was clarified by MO calculations. X-ray and UV/vis studies indicated that the covalently linked quinone moieties bear a large torsional angle. Nevertheless, the reduction potentials rose significantly with the order of monomer < dimer < trimer, indicating that the negative charge was efficiently delocalized within the radical anions.

  DOI：

  10.1021/ol702289u

文献信息

• Exchange of Quinone and Hydroquinone Moieties in Mixed Solutions of Biquinone and Bihydroquinone
  作者：Naoto Hayashi、Kiyomi Matsui、Akifumi Kanda、Takahiro Yoshikawa、Hiroyuki Nakagawa、Junro Yoshino、Hiroyuki Higuchi

  DOI：10.1246/cl.2011.947

  日期：2011.9.5

  A mixture of biquinone (QQn) and bihydroquinone (HHn) bearing tert-butyl substituents at 5,5′- (n = 1) and 6,6′-positions (n = 2) yields hydroquinonylquinone (HQn) as an equilibrium product by quinone/hydroquinone exchange. The equilibrium constants for the formation of HQ1 are higher than those of HQ2 in all solvents. While the exchange between QQ1 and HH1 is slow, that between HQ1s occurs so rapidly in CDCl3 that it is observed in phase-sensitive 2D NOESY NMR spectra.

  一种混合物，包括在5,5′-位（n = 1）和6,6′-位（n = 2）处具有叔丁基取代基的双醌（QQn）和双氢醌（HHn），通过醌/氢醌交换生成氢醌基双醌（HQn）作为平衡产物。在所有溶剂中，HQ1的形成平衡常数高于HQ2。尽管QQ1和HH1之间的交换较慢，但HQ1之间的交换在CDCl3中发生得非常迅速，以至于在相敏感的2D NOESY NMR光谱中得以观察到。
• Quinone Dimers Connected by 1,4-Phenylene and 2,5-Thienylene Moieties as a π Linker
  作者：Naoto Hayashi、Teru Sakakibara、Takahiro Ohnuma、Junro Yoshino、Hiroyuki Higuchi

  DOI：10.3987/com-09-s(s)108

  日期：——

  The synthesis and characterization of quinone dimers connected by 1,4-phenylene (QPQ) and 2,5-thienylene (QTQ) linkers are described. QPQ and QTQ were synthesized by means of Suzuki coupling and subsequent oxidation. Significant bathochromic shifts were observed in the electronic absorption spectra of QPQ and QTQ as compared to that of the quinine dimers without a linker. In addition, cyclic voltammetry and DFT calculations demonstrated that QTQ was a stronger electron acceptor than QPQ due to its planar structure, even though QTQ contains an electron-rich thiophene ring.
• Synthesis, Structure, and Properties of Benzoquinone Dimer and Trimers Bearing <i>t</i>-Bu Substituents
  作者：Naoto Hayashi、Takahiro Yoshikawa、Takahiro Ohnuma、Hiroyuki Higuchi、Katsuya Sako、Hidehiro Uekusa

  DOI：10.1021/ol702289u

  日期：2007.12.1

  Highly soluble and stable quinone dimer and trimers were successfully yielded by introduction of t-Bu substituents. In X-ray structure analysis, the dimer quinone moiety was distorted into the boat shape, which was clarified by MO calculations. X-ray and UV/vis studies indicated that the covalently linked quinone moieties bear a large torsional angle. Nevertheless, the reduction potentials rose significantly with the order of monomer < dimer < trimer, indicating that the negative charge was efficiently delocalized within the radical anions.
• Synthesis and testing of chromogenic phenoxazinone substrates for β-alanyl aminopeptidase
  作者：Andrey V. Zaytsev、Rosaleen J. Anderson、Alexandre Bedernjak、Paul W. Groundwater、Yongxue Huang、John D. Perry、Sylvain Orenga、Celine Roger-Dalbert、Arthur James

  DOI：10.1039/b716978g

  日期：——

  salts 27a-d have been synthesized and tested as chromogenic substrates for beta-alanyl aminopeptidase, which is present in Pseudomonas aeruginosa, the most common respiratory pathogen in patients with cystic fibrosis. The biological results show that 7-N-(beta-alanyl)amino-1-pentylphenoxazin-3-one trifluoroacetate salt 27a is a chromogenic substrate for this bacterium, with a low degree of diffusion

  已合成新型7-N-（β-丙氨酰基）氨基苯恶嗪-3-酮盐27a-d并作为β-丙氨酰氨基肽酶的生色底物进行了测试，该酶存在于铜绿假单胞菌中，铜绿假单胞菌是囊性纤维化患者中最常见的呼吸道病原体。生物学结果表明，7-N-（β-丙氨酰基）氨基-1-戊基苯恶嗪-3-一三氟乙酸盐27a是该细菌的发色底物，在营养培养基中的扩散程度低，可用于细菌培养和明亮的培养。红色，使其很容易与琼脂背景区分开。