3,4-bis(p-methoxythiophenoxy)-3-cyclobutene-1,2-dione | 551959-28-5

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 3,4-bis(p-methoxythiophenoxy)-3-cyclobutene-1,2-dione
• 英文别名: 3,4-bis[(4-methoxyphenyl)thio]-3-cyclobutene-1,2-dione；3,4-bis-(4-methoxyphenylthio)cyclobutenedione；3,4-Bis[(4-methoxyphenyl)sulfanyl]cyclobut-3-ene-1,2-dione
• CAS: 551959-28-5
• 化学式: C₁₈H₁₄O₄S₂
• 分子量: 358.439
• InChiKey: XIQLKBNCBJJYOT-UHFFFAOYSA-N

物化性质

• 熔点：
  133 °C(Solv: ethyl acetate (141-78-6); hexane (110-54-3))
• 沸点：
  497.2±55.0 °C(Predicted)
• 密度：
  1.40±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  103
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3,4-bis(p-methoxythiophenoxy)-3-cyclobutene-1,2-dione 、 三丁基(4-氯苯基)锡烷 在 tris(dibenzylideneacetone)dipalladium (0) 噻吩-2-甲酸亚铜(I) 、 三(2-呋喃基)膦 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 以37%的产率得到3,4-bis(4-chlorophenyl)cyclobut-3-ene-1,2-dione
  参考文献：
  名称：

  Pd-Catalyzed, Cu(I)-Mediated Cross-Couplings of Bisarylthiocyclobutenediones with Boronic Acids and Organostannanes

  摘要：

  Bisarylthiocyclobutenedione 7 reacted smoothly with a variety of both organostannanes and (hetero)arylboronic acids in the presence of a catalytic amount of Pd and a stoichiometric amount of CuTC to produce symmetrical disubstituted cyclobutenediones in yields that range from 37 to 94% (18 examples).

  DOI：

  10.1021/jo701331m
• 作为产物：
  描述：

  3,4-二氯-3-环丁烯-1,2-二酮 、 4-甲氧基苯硫酚 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 生成 3,4-bis(p-methoxythiophenoxy)-3-cyclobutene-1,2-dione
  参考文献：
  名称：

  Pd-Catalyzed, Cu(I)-Mediated Cross-Couplings of Bisarylthiocyclobutenediones with Boronic Acids and Organostannanes

  摘要：

  Bisarylthiocyclobutenedione 7 reacted smoothly with a variety of both organostannanes and (hetero)arylboronic acids in the presence of a catalytic amount of Pd and a stoichiometric amount of CuTC to produce symmetrical disubstituted cyclobutenediones in yields that range from 37 to 94% (18 examples).

  DOI：

  10.1021/jo701331m

文献信息

• Synthesis and characterization of cyclobutenedione–bithiophene π-conjugated polymers: acetal-protecting strategy for Kumada–Tamao–Corriu coupling polymerization between aryl bromide and Grignard reagents
  作者：Tomoyuki Ohishi、Takuma Sone、Kohei Oda、Akihiro Yokoyama

  DOI：10.1039/c9ra08275a

  日期：——

  Kumada–Tamao–Corriu coupling polymerization of a cyclobutenedione monomer whose carbonyl groups are protected as acetals was achieved. Hydrolysis of the acetals afforded donor–acceptor type π-conjugated polymers consisting of cyclobutenedione as an acceptor unit and bithiophene as a donor unit. The acetal-protected monomer was also subjected to Suzuki–Miyaura coupling polymerization. The absorption and emission

  环丁烯二酮是一种芳香环，具有很强的吸电子性能，但容易与亲核试剂发生不希望的反应。在此，实现了羰基被保护为缩醛的环丁烯二酮单体的 Kumada-Tamao-Corriu 偶联聚合。缩醛的水解提供了由环丁烯二酮作为受体单元和二噻吩作为供体单元组成的供体-受体型π-共轭聚合物。缩醛保护的单体也进行了 Suzuki-Miyaura 偶联聚合。与乙缩醛保护的聚合物相比，去保护聚合物的吸收和发射光谱向更长的波长移动。
• Synthesis bis-thienyl-substituted cyclobutenedione via the Liebeskind-Srogl and Stille cross-coupling reactions
  作者：Siddhant V. Kokate、Angélica Aguilar-Aguilar、Miguel A. Vázquez-Guevara、Gabriel Luna-Bárcenas、Alejandro J. Gimenez、Eduardo Peña-Cabrera

  DOI：10.24820/ark.5550190.p011.459

  日期：——
• Pd-Catalyzed, Cu(I)-Mediated Cross-Couplings of Bisarylthiocyclobutenediones with Boronic Acids and Organostannanes
  作者：Angélica Aguilar-Aguilar、Lanny S. Liebeskind、Eduardo Peña-Cabrera

  DOI：10.1021/jo701331m

  日期：2007.10.1

  Bisarylthiocyclobutenedione 7 reacted smoothly with a variety of both organostannanes and (hetero)arylboronic acids in the presence of a catalytic amount of Pd and a stoichiometric amount of CuTC to produce symmetrical disubstituted cyclobutenediones in yields that range from 37 to 94% (18 examples).