4-Phenyl-3-(trimethylsilyl)furan | 148367-35-5

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: 4-Phenyl-3-(trimethylsilyl)furan
• 英文别名: Trimethyl-(4-phenylfuran-3-yl)silane
• CAS: 148367-35-5
• 化学式: C₁₃H₁₆OSi
• 分子量: 216.355
• InChiKey: SFCOUEMLPCBRDH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.49
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  13.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-Phenyl-3-(trimethylsilyl)furan 在 四(三苯基膦)钯 2,3-双(溴甲基)喹喔啉 、 三氯化硼 、 sodium carbonate 作用下， 生成 4,4'-Diphenyl-3,3'-bifuran
  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：

  三甲硅基丙炔醇 在 对甲苯磺酸 作用下， 以 四氢呋喃 、 环己烷 、 苯 为溶剂， 反应 22.0h， 生成 4-Phenyl-3-(trimethylsilyl)furan
  参考文献：
  名称：

  镁介导的炔丙醇的碳金属化：呋喃和呋喃酮的直接途径

  摘要：

  描述了将乙烯基和芳基格氏试剂添加到炔丙醇中以从一锅法反应直接合成呋喃和丁烯内酯。这些产物由推定的镁螯合中间体2与各种亲电试剂反应生成。该螯合物也是由炔基锂加成醛，然后进行镁交换和格利雅加成而原位生成的。因此，可以通过明智地选择底物和试剂来控制呋喃环的完全取代模式。

  DOI：

  10.1016/s0040-4039(99)01995-4

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; 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：——
• 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：——
• Magnesium mediated carbometallation of propargyl alcohols: direct routes to furans and furanones
  作者：Pat Forgione、Peter D. Wilson、Alex G. Fallis

  DOI：10.1016/s0040-4039(99)01995-4

  日期：2000.1

  The addition of vinyl and aryl Grignard reagents to propargyl alcohols for the direct synthesis of furans and butenolides from a one pot reaction is described. These products arise from a putative magnesium chelate intermediate 2 upon reaction with various electrophiles. This chelate was also generated in situ from alkynyl lithium addition to aldehydes followed by magnesium exchange and Grignard addition

  描述了将乙烯基和芳基格氏试剂添加到炔丙醇中以从一锅法反应直接合成呋喃和丁烯内酯。这些产物由推定的镁螯合中间体2与各种亲电试剂反应生成。该螯合物也是由炔基锂加成醛，然后进行镁交换和格利雅加成而原位生成的。因此，可以通过明智地选择底物和试剂来控制呋喃环的完全取代模式。
• 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.