1-[5-(4,4,5,5-tetramethyl[1.3.2]dioxaborolan-2-yl)-4-trimethylsilanyl-isoxazol-3-yl]-ethanone | 862126-47-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-[5-(4,4,5,5-tetramethyl[1.3.2]dioxaborolan-2-yl)-4-trimethylsilanyl-isoxazol-3-yl]-ethanone
• 英文别名: 1-[5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-4-(trimethylsilyl)-3-isoxazolyl]ethanone；1-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-4-trimethylsilyl-1,2-oxazol-3-yl]ethanone
• CAS: 862126-47-4
• 化学式: C₁₄H₂₄BNO₄Si
• 分子量: 309.245
• InChiKey: KKHQUNSUWYHZSU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.72
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  61.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  甲酸 、 三甲基(4,4,5,5-四甲基)-1,3,2-二氧硼烷-2-基)乙炔硅烷 在 ammonium cerium(IV) nitrate 作用下， 以 丙酮 为溶剂， 反应 10.0h， 生成 1-[5-(4,4,5,5-tetramethyl[1.3.2]dioxaborolan-2-yl)-4-trimethylsilanyl-isoxazol-3-yl]-ethanone 、 1-[4-(4,4,5,5-tetramethyl[1.3.2]dioxaborolan-2-yl)-5-trimethylsilanyl-isoxazol-3-yl]-ethanone
  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.