4-(3',4',5'-Trimethoxybenzyl)-3-(trimethylsilyl)furan | 153799-53-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-(3',4',5'-Trimethoxybenzyl)-3-(trimethylsilyl)furan
• 英文别名: Trimethyl-[4-[(3,4,5-trimethoxyphenyl)methyl]furan-3-yl]silane
• CAS: 153799-53-2
• 化学式: C₁₇H₂₄O₄Si
• 分子量: 320.461
• InChiKey: BBBXDYDWDVJTHN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.44
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  40.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(3',4',5'-Trimethoxybenzyl)-3-(trimethylsilyl)furan 在 四(三苯基膦)钯 三氯化硼 、 sodium carbonate 作用下， 生成 3-(3',4',5'-Trimethoxybenzyl)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 、 3,4,5-三甲氧基苄氯 生成 4-(3',4',5'-Trimethoxybenzyl)-3-(trimethylsilyl)furan
  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

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.
• 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.