3,4-Bis(trimethylsilyl)furan-2-carbaldehyde

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,4-Bis(trimethylsilyl)furan-2-carbaldehyde
• 化学式: C₁₁H₂₀O₂Si₂
• 分子量: 240.45
• InChiKey: ADTRVVMCDQLTIH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.18
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  30.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1,1-二氯甲醚 、 3,4-Bis(trimethylsilyl)furan 在 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以65%的产率得到3,4-Bis(trimethylsilyl)furan-2-carbaldehyde
  参考文献：
  名称：

  Regiospecific synthesis of 3,4-disubstituted furans. 7. Synthesis and reactions of 3,4-bis(trimethylsilyl)furan: Diels-Alder cycloaddition, Friedel-Crafts acylation, and regiospecific conversion to 3,4-disubstituted furans

  摘要：

  As a versatile building block, 3,4-bis(trimethylsilyl)furan (1), conveniently obtained through a Diels-Alder reaction between 4-phenyloxazole and bis(trimethylsilyl)acetylene, was able to undergo Diels-Alder cycloadditions with dienophiles. In two separate experiments, extrusion of bis(trimethylsilyl)acetylene occurred when 1 was treated with acetylenic dienophiles. Furan 1 was also found to undergo Friedel-Crafts acylations at the unsubstituted alpha-position in general and gave a pair of regioisomers. Moreover, 1 was converted regiospecifically to various 3,4-disubstituted furans, utilizing consecutively and repeatedly an ipso displacement of the trimethylsilyl group with boron trichloride and a novel palladium-catalyzed Suzuki-type coupling reaction of the resulting boroxines.

  DOI：

  10.1021/jo00093a025