4--3-(trimethylsilyl)furan | 153799-51-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4--3-(trimethylsilyl)furan
• 英文别名: 4-(p-methoxycarbonylbenzyl)-3-(trimethylsilyl)furan；Methyl 4-[(4-trimethylsilylfuran-3-yl)methyl]benzoate
• CAS: 153799-51-0
• 化学式: C₁₆H₂₀O₃Si
• 分子量: 288.418
• InChiKey: POFYYPGOKRTJRR-UHFFFAOYSA-N

物化性质

• 沸点：
  367.2±42.0 °C(Predicted)
• 密度：
  1.07±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  39.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4--3-(trimethylsilyl)furan 在 silver tetrafluoroborate 、 碘 、 三氯化硼 作用下， 生成 3-Iodo-4-furan
  参考文献：
  名称：

  Regiospecific synthesis of furan-3,4-diyl oligomers via palladium-catalyzed self-coupling of organoboroxines

  摘要：

  The palladium-catalyzed reaction of organoboroxines 2 and o-bis(bromomethyl)arenes 1 produced regiospecifically the cross-coupled products 3 and the corresponding dimeric bifurans 4. This method has been successfully applied to the synthesis of symmetrical, as well as unsymmetrical furan-3,4-diyl dimers, trimers, and tetramers. A furan-3,4-diyl octamer was also obtained by utilizing this method.

  DOI：

  10.1021/jo00080a009
• 作为产物：
  描述：

  3,4-Bis(trimethylsilyl)furan 在 四(三苯基膦)钯 、 碘 、 silver trifluoroacetate 、 铜 、 锌 作用下， 以 四氢呋喃 为溶剂， 反应 9.0h， 生成 4--3-(trimethylsilyl)furan
  参考文献：
  名称：

  Song, Zhi Zhong; Wong, Henry N. C., Liebigs Annalen der Chemie, 1994, # 1, p. 29 - 34

  摘要：

  DOI：

文献信息

• 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
  作者：Zhi Zhong Song、Mei Sing Ho、Henry N. C. Wong

  DOI：10.1021/jo00093a025

  日期：1994.7

  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.