2,6-dihydroxymethylphenylboronic acid | 1195621-90-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2,6-dihydroxymethylphenylboronic acid
• 英文别名: [2,6-Bis(hydroxymethyl)phenyl]boronic acid
• CAS: 1195621-90-9
• 化学式: C₈H₁₁BO₄
• 分子量: 181.984
• InChiKey: AXZKCBMJVKLMFI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.65
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  80.9
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborole-7-carbaldehyde 在 sodium tetrahydroborate 作用下， 生成 2,6-dihydroxymethylphenylboronic acid
  参考文献：
  名称：

  Convenient and versatile synthesis of formyl-substituted benzoxaboroles

  摘要：

  Despite of the medicinal significance of benzoxaboroles, with the newly discovered clinical compound AN2690 as an example, the synthetic method for rapid diversification of this novel scaffold is lacking. To this end, a versatile and scalable synthesis of formyl-substituted benzoxaboroles is described here. A key step is the mono-oxidation of the two hydroxyls in compound 4 by taking advantage of the stable oxaborole ring in non-coordinating solvents, which was devised based on the study of the intramolecular coordination and exchange properties. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.08.026