4-bromo-5-(triethylsilyl)thiophene-2-carboxaldehyde | 1354032-41-9

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 4-bromo-5-(triethylsilyl)thiophene-2-carboxaldehyde
• CAS: 1354032-41-9
• 化学式: C₁₁H₁₇BrOSSi
• 分子量: 305.311
• InChiKey: FVQVENDDPKVQPC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.04
• 重原子数：
  15.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  三乙基氯硅烷 在 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 4.5h， 生成 4-bromo-5-(triethylsilyl)thiophene-2-carboxaldehyde
  参考文献：
  名称：

  Directed metalation and regioselective functionalization of 3-bromofuran and related heterocycles with NaHMDS

  摘要：

  A mild and regioselective functionalization protocol for 3-bromofuran and analogs has been developed. Selective metalation and functionalization of C2 can be achieved as a result of the directing effect of the adjacent electron-withdrawing bromo group. In addition, the C5 position can also be selectively functionalized by blocking the C2 position via silylation or by simply controlling the reaction temperature. These functionalized compounds bearing a C3 bromo substituent may be further elaborated by utilizing a Suzuki-Miyaura cross-coupling procedure. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.10.158