3-decyl-1-hydroxy-3H-2,1-benzoxaborole | 952149-29-0

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: 3-decyl-1-hydroxy-3H-2,1-benzoxaborole
• CAS: 952149-29-0
• 化学式: C₁₇H₂₇BO₂
• 分子量: 274.211
• InChiKey: KVOLDTGMQZWZSE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.98
• 重原子数：
  20
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-溴吡啶 、 3-decyl-1-hydroxy-3H-2,1-benzoxaborole 在 四(三苯基膦)钯 sodium carbonate 作用下， 以 甲苯 为溶剂， 以91%的产率得到1-(2-(pyridin-2-yl)phenyl)-1-undecanol
  参考文献：
  名称：

  Practical synthesis and applications of benzoboroxoles

  摘要：

  A convenient one-pot synthesis of benzoboroxoles has been developed via the reaction of o-bromobenzyl alcohols with NaH, (BuLi)-Bu-n, and B((OPr)-Pr-i)(3) followed by acidic hydrolysis. Applications of these benzoboroxoles have been demonstrated in Pd-catalyzed cross-coupling reactions and the protocol has been extended for the synthesis of a chiral benzoboroxole. Exceptionally short synthesis of a potent antifungal agent AN2690 and several of its analogs has also been realized. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.06.099
• 作为产物：
  描述：

  Decylmagnesium bromide 在 正丁基锂 、 sodium hydride 作用下， 以 乙醚 为溶剂， 生成 3-decyl-1-hydroxy-3H-2,1-benzoxaborole
  参考文献：
  名称：

  Practical synthesis and applications of benzoboroxoles

  摘要：

  A convenient one-pot synthesis of benzoboroxoles has been developed via the reaction of o-bromobenzyl alcohols with NaH, (BuLi)-Bu-n, and B((OPr)-Pr-i)(3) followed by acidic hydrolysis. Applications of these benzoboroxoles have been demonstrated in Pd-catalyzed cross-coupling reactions and the protocol has been extended for the synthesis of a chiral benzoboroxole. Exceptionally short synthesis of a potent antifungal agent AN2690 and several of its analogs has also been realized. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.06.099