6-(4-aminophenoxy)benzo[c][1,2]oxaborol-1(3H)-ol | 1196473-50-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-(4-aminophenoxy)benzo[c][1,2]oxaborol-1(3H)-ol
• 英文别名: 4-[(1-hydroxy-3H-2,1-benzoxaborol-6-yl)oxy]aniline
• CAS: 1196473-50-3
• 化学式: C₁₃H₁₂BNO₃
• 分子量: 241.054
• InChiKey: INUBKLXXHFEIEY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.28
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  64.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-溴-4-氟苯甲醛 在 盐酸 、 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 sodium tetrahydroborate 、 potassium acetate 、 caesium carbonate 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 6-(4-aminophenoxy)benzo[c][1,2]oxaborol-1(3H)-ol
  参考文献：
  名称：

  Synthesis and SAR of novel benzoxaboroles as a new class of β-lactamase inhibitors

  摘要：

  A new class of benzoxaborole beta-lactamase inhibitors were designed and synthesized. 6-Aryloxy benzoxaborole 22 inhibited AmpC P99 and CMY-2 with K-i values in the low nanomolar range. Compound 22 restored antibacterial activity of ceftazidime against Enterobacter cloacae P99 expressing AmpC, a class C beta-lactamase enzyme. The SAR around the arylbenzoxaboroles, which included the influence of linker and substitutions was also established. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.02.024

文献信息

• BORON-CONTAINING SMALL MOLECULES
  申请人：Xia Yi

  公开号：US20100256092A1

  公开（公告）日：2010-10-07

  This invention relates to, among other items, 6-substituted benzoxaborole compounds and their use for treating bacterial infections.

  这项发明涉及6-取代苯硼酯化合物等物品，以及它们用于治疗细菌感染的用途。
• Transition-metal-free, one-pot synthesis of benzoxaboroles from <i>o</i>-bromobenzaldehydes <i>via</i> visible-light-promoted borylation
  作者：Jinghan Luo、Xingxing Jia、Yanjun Hu、Jianchao Chen、Tiemin Sun

  DOI：10.1039/d1ob01853a

  日期：——

  A novel and simple one-pot stepwise method to synthesize benzoxaboroles was demonstrated. This step-by-step synthetic method includes photocatalytic boronization with phenothiazine as a photocatalyst and sequential water-induced reduction in the presence of bis(pinacolato)diboron. A series of o-bromobenzaldehydes were well-tolerated under the standard conditions. In addition, this method has been successfully

  展示了一种新颖且简单的一锅法逐步合成苯并恶硼烷的方法。这种分步合成方法包括使用吩噻嗪作为光催化剂的光催化硼化和在双（频哪醇）二硼存在下的连续水诱导还原。一系列邻溴苯甲醛在标准条件下具有良好的耐受性。此外，该方法已成功应用于抗结核候选药物GSK 3036656和抗真菌药物tavaborole的合成。