3-bromo-4-(4,4,5,5-tetramethyl[1.3.2]dioxaborolan-2-yl)-isoxazole

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 芳基卤化物
• 英文名称: 3-bromo-4-(4,4,5,5-tetramethyl[1.3.2]dioxaborolan-2-yl)-isoxazole
• 英文别名: 3-Bromo-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2-oxazole；3-bromo-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2-oxazole
• 化学式: C₉H₁₃BBrNO₃
• 分子量: 273.922
• InChiKey: OFFHJBBCYKMEGP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.74
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  44.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1,1-二溴甲醛肟 、 2-乙炔-4,4,5,5-四甲基-[1,3,2]二噁硼烷 在 potassium hydrogencarbonate 作用下， 以 乙二醇二甲醚 为溶剂， 生成 3-bromo-5-(4,4,5,5-tetramethyl[1.3.2]dioxaborolan-2-yl)-isoxazole 、 3-bromo-4-(4,4,5,5-tetramethyl[1.3.2]dioxaborolan-2-yl)-isoxazole
  参考文献：
  名称：

  Investigation of the scope of a [3+2] cycloaddition approach to isoxazole boronic esters

  摘要：

  The [3 + 2] cycloaddition reaction of nitrile oxides and alkynylboronates provides direct access to a wide variety of isoxazole boronic esters. Specifically, this technique has been employed to generate trisubstituted isoxazole 4-boronates and disubstituted isoxazoles where the boronic ester moiety can be installed at C-4 or C-5 with high levels of regiocontrol. The application of this methodology in the synthesis of non-steroidal antiinflammatory agents is also described. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.05.015

文献信息

• Investigation of the scope of a [3+2] cycloaddition approach to isoxazole boronic esters
  作者：Jane E. Moore、Mark W. Davies、Katharine M. Goodenough、Robert A.J. Wybrow、Mark York、Christopher N. Johnson、Joseph P.A. Harrity

  DOI：10.1016/j.tet.2005.05.015

  日期：2005.7

  The [3 + 2] cycloaddition reaction of nitrile oxides and alkynylboronates provides direct access to a wide variety of isoxazole boronic esters. Specifically, this technique has been employed to generate trisubstituted isoxazole 4-boronates and disubstituted isoxazoles where the boronic ester moiety can be installed at C-4 or C-5 with high levels of regiocontrol. The application of this methodology in the synthesis of non-steroidal antiinflammatory agents is also described. (c) 2005 Elsevier Ltd. All rights reserved.