双(4-甲氧基苯基)硼酸 | 73774-45-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 双(4-甲氧基苯基)硼酸
• 英文名称: di-(4-methoxyphenyl)borinic acid
• 英文别名: bis(4-methoxyphenyl)borinic acid
• CAS: 73774-45-5
• 化学式: C₁₄H₁₅BO₃
• 分子量: 242.082
• InChiKey: ZNGBSXNRDFTNEG-UHFFFAOYSA-N

物化性质

• 熔点：
  107 °C
• 沸点：
  386.3±52.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  双(4-甲氧基苯基)硼酸 在 水 、 溴 作用下， 生成 4-甲氧基苯硼酸
  参考文献：
  名称：

  Mel'nikow, Zhurnal Obshchei Khimii, 1936, vol. 6, p. 636,638,639

  摘要：

  DOI：
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 三氯化硼 作用下， 以 四氢呋喃 为溶剂， 生成 双(4-甲氧基苯基)硼酸
  参考文献：
  名称：

  Identification of Borinic Esters as Inhibitors of Bacterial Cell Growth and Bacterial Methyltransferases, CcrM and MenH

  摘要：

  As bacteria continue to develop resistance toward current antibiotics, we find ourselves in a continual battle to identify new antibacterial agents and targets. We report herein a class of boron-containing compounds termed borinic esters that have broad spectrum antibacterial activity with minimum inhibitory concentrations (MIC) in the low microgram/mL range. These compounds were identified by screening for inhibitors against Caulobacter crescentus CcrM, an essential DNA methyltransferase from Gram negative alpha-proteobacteria. In addition, we demonstrate that borinic esters inhibit menaquinone methyltransferase in Gram positive bacteria using a new biochemical assay for MenH from Bacillus subtilis. Our data demonstrate the potential for further development of borinic esters as antibacterial agents as well as leads to explore more specific inhibitors against two essential bacterial enzymes.

  DOI：

  10.1021/jm050676a
• 作为试剂：
  描述：

  6-(苄氧基)-1-己醇 、 1,2-anhydro-3,4,6-tri-O-benzyl-β-D-mannopyranose 在 双(4-甲氧基苯基)硼酸 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以62%的产率得到
  参考文献：
  名称：

  糖基受体衍生的硼酸酯促进的直接和β-立体选择性甘露糖基化与1,2-脱水甘露糖供体

  摘要：

  在糖基受体衍生的硼酸酯存在下，使用1,2-脱水甘露糖供体和单醇受体进行β-立体选择性甘露糖基化。反应在温和条件下平稳进行，以中等至高产率提供具有高立体选择性的相应β-甘露糖苷。此外，本糖基化方法已成功地应用于阿莫莫尼脂A的全合成。

  DOI：

  10.1021/acs.orglett.6b00926

文献信息

• Highly efficient palladium-catalyzed cross-coupling of diarylborinic acids with arenediazoniums for practical diaryl synthesis
  作者：Fengze Wang、Chen Wang、Guoping Sun、Gang Zou

  DOI：10.1016/j.tetlet.2019.151491

  日期：2020.2

  A highly efficient cross-coupling of cost-effective diarylborinic acids with both isolatable and latent arenediazoniums, i.e. tetrafluoroborates and aryltriazenes, respectively, has been developed with a practical palladium catalyst system under base-free conditions in open flask at room temperature. A variety of electronically and sterically various biaryls, in particular, those bearing a coordinative

  低成本的二芳基硼酸与可分离的和潜在的芳族重氮鎓（即四氟硼酸酯和芳基三氮烯）的高效交叉偶联已在实用的钯催化剂体系下，在无碱条件下于室温下在敞口烧瓶中开发出来。通过使用0.3mol％的乙酸钯作为催化剂，可以以良好或优异的产率获得多种电子和空间上不同的联芳基，特别是那些带有配位邻位取代基的联芳基。该方案的特征包括二芳基硼酸的成本效益，对杂原子邻位取代底物的功效以及对芳基氯化物的高化学选择性，已在杀菌剂Boscalid的实际合成中得到了明确证明。
• Treatment of bacterial induced diseases using DNA methyl transferase inhibitors
  申请人：Benkovic J. Stephen

  公开号：US20050227933A1

  公开（公告）日：2005-10-13

  Methods for treating and/or preventing disease conditions caused or induced or aggravated by microbes, especially bacteria, by inhibiting DNA methyltransferase activity, such as by administering to an animal a DNA methyltransferase inhibitor, are disclosed, along with methods of reducing or ablating virulence in bacteria by inhibiting DNA methyltransferase activity.

  通过抑制DNA甲基转移酶活性，例如通过向动物施用DNA甲基转移酶抑制剂，来治疗和/或预防由微生物，特别是细菌引起、诱导或加重的疾病状况的方法被揭示，同时还揭示了通过抑制DNA甲基转移酶活性来减少或消除细菌的毒力的方法。
• Base-assisted, copper-catalyzed N-arylation of (benz)imidazoles and amines with diarylborinic acids
  作者：Changwei Guan、Yuanyuan Feng、Gang Zou、Jie Tang

  DOI：10.1016/j.tet.2017.10.043

  日期：2017.12

  cost-effective aryl source has been efficiently effected via Cu(OAc)2-catalyzed Chan-Lam coupling in assistance of tetramethylethylenediamine (TMEDA) in methanol and pyridine (Py) in dichloromethane, respectively, in air at room temperature. The diarylborinic acids could be well accommodated by the Chan-Lam coupling oxidative conditions containing a proper combination of bases and solvents. The steric

  借助Cu（OAc）2催化的Chan-Lam偶联，借助四甲基乙二胺（TMEDA）在甲醇和吡啶（Py）中的催化作用，已有效地实现了（苯）咪唑和胺与二芳基硼酸作为具有成本效益的芳基源的N-芳基化作用。室温下分别置于二氯甲烷中。包含适当的碱和溶剂组合的Chan-Lam偶联氧化条件可以很好地容纳二芳基硼酸。与电子因素相比，使用高阶芳基硼试剂时，空间位阻似乎对铜催化的N-芳基化的影响更大，尤其是对于低反应性苯胺和脂肪族胺而言。
• Borinic acid catalysed peptide synthesis
  作者：Tharwat Mohy El Dine、Jacques Rouden、Jérôme Blanchet

  DOI：10.1039/c5cc06177f

  日期：——

  2-Chlorophenylborinic acid is reported to catalyze dipeptide synthesis in the presence of molecular sieves with no racemization.

  2-氯苯硼酸据报道在分子筛存在下催化二肽合成，且无外消旋作用。
• Palladium-Catalyzed Cross-CouplingReaction of Potassium Diaryldifluoroborates with Aryl Halides
  作者：Takatoshi Ito、Toshiyuki Iwai、Takumi Mizuno、Yoshio Ishino

  DOI：10.1055/s-2003-40851

  日期：——

  The catalytic cross-coupling reaction of potassium di­aryldifluoroborates with aryl halides proceeds to afford the biphenyls in good yields. These salts on an arylation reagent were readily prepared via a protocol of the Grignard method and transformation to potassium salts. Two aryl groups of these salts were efficiently transferred in the Suzuki-Miyaura reaction.

  钾二芳基二氟硼酸盐与芳烃卤化物的催化交叉耦合反应能够以良好的产率产生产酚。通过格氏试剂法及转化为钾盐的步骤，这些盐作为芳烃化试剂被容易制备。通过铃木-宫浦反应，这些盐的两个芳基高效转移。