1-(furan-2-yl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propan-2-ol | 1226953-86-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 硼酸衍生物
• 英文名称: 1-(furan-2-yl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propan-2-ol
• CAS: 1226953-86-1
• 化学式: C₁₃H₂₁BO₄
• 分子量: 252.118
• InChiKey: UIEAJMOULYSUOM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  51.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-呋喃基乙酮 、 联硼酸频那醇酯 在 [1,3-dicyclohexylimidazol-2-yl]copper(I) chloride 、 sodium t-butanolate 、 silica gel 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以87%的产率得到1-(furan-2-yl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propan-2-ol
  参考文献：
  名称：

  Copper-Catalyzed Diboration of Ketones: Facile Synthesis of Tertiary α-Hydroxyboronate Esters

  摘要：

  The diboration of ketones with the (ICy)CuOt-Bu catalyst was developed to provide access to tertiary alpha-hydroxyboronate esters. The (ICy)CuOt-Bu catalyst was generated in situ with (ICy)CuCI and NaOt-Bu to afford a more efficient catalyst than the preformed (ICy)CuOt-Bu. These conditions result in the diboration of various ketones in toluene at 50 degrees C in 2-22 h. Treatment of the resulting products with silica gel affords the corresponding a-hydroxyboronate esters.

  DOI：

  10.1021/ol100468f

文献信息

• Copper-Catalyzed Diboration of Ketones: Facile Synthesis of Tertiary α-Hydroxyboronate Esters
  作者：Melissa L. McIntosh、Cameron M. Moore、Timothy B. Clark

  DOI：10.1021/ol100468f

  日期：2010.5.7

  The diboration of ketones with the (ICy)CuOt-Bu catalyst was developed to provide access to tertiary alpha-hydroxyboronate esters. The (ICy)CuOt-Bu catalyst was generated in situ with (ICy)CuCI and NaOt-Bu to afford a more efficient catalyst than the preformed (ICy)CuOt-Bu. These conditions result in the diboration of various ketones in toluene at 50 degrees C in 2-22 h. Treatment of the resulting products with silica gel affords the corresponding a-hydroxyboronate esters.