4-(p-nitrobenzyl)-3-(trimethylsilyl)furan | 148367-44-6

• 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-(p-nitrobenzyl)-3-(trimethylsilyl)furan
• 英文别名: 3-p-nitrobenzyl-4-trimethylsilyl-furan；Trimethyl-[4-[(4-nitrophenyl)methyl]furan-3-yl]silane
• CAS: 148367-44-6
• 化学式: C₁₄H₁₇NO₃Si
• 分子量: 275.379
• InChiKey: IAQXFLDBFLRAMB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.32
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  59
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(p-nitrobenzyl)-3-(trimethylsilyl)furan 在 四(三苯基膦)钯 silver tetrafluoroborate 、 碘 、 三氯化硼 、 sodium carbonate 作用下， 反应 20.0h， 生成 4-(Trimethylsilyl)-4"-(p-nitrobenzyl)-3,3':4',3"-terfuran
  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 bis(triphenylphosphine)nickel(II) chloride 、 碘 、 silver trifluoroacetate 作用下， 以 四氢呋喃 为溶剂， 反应 7.0h， 生成 4-(p-nitrobenzyl)-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.
• Song, Zhi Zhong; Zhou, Zhong Yuan; Mak, Thomas C. W., Angewandte Chemie, 1993, vol. 105, # 3, p. 406 - 408
  作者：Song, Zhi Zhong、Zhou, Zhong Yuan、Mak, Thomas C. W.、Wong, Henry N. C.

  DOI：——

  日期：——
• Song, Zhi Zhong; Wong, Henry N. C., Liebigs Annalen der Chemie, 1994, # 1, p. 29 - 34
  作者：Song, Zhi Zhong、Wong, Henry N. C.

  DOI：——

  日期：——
• Regiospecific synthesis of furan-3,4-diyl oligomers via palladium-catalyzed self-coupling of organoboroxines
  作者：Zhi Zhong Song、Henry N. C. Wong

  DOI：10.1021/jo00080a009

  日期：1994.1

  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.