3-(4-Methoxyphenyl)sulfanyl-4-(4-methylphenyl)cyclobut-3-ene-1,2-dione | 956110-82-0

• 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-Methoxyphenyl)sulfanyl-4-(4-methylphenyl)cyclobut-3-ene-1,2-dione
• CAS: 956110-82-0
• 化学式: C₁₈H₁₄O₃S
• 分子量: 310.373
• InChiKey: LRCSKFNFSDAKCI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  68.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(4-Methoxyphenyl)sulfanyl-4-(4-methylphenyl)cyclobut-3-ene-1,2-dione 、 6-甲氧基萘-2-硼酸 在 tris(dibenzylideneacetone)dipalladium (0) 三(2-呋喃基)膦 作用下， 以 四氢呋喃 为溶剂， 反应 20.0h， 以50%的产率得到3-(6-Methoxynaphthalen-2-yl)-4-(4-methylphenyl)cyclobut-3-ene-1,2-dione
  参考文献：
  名称：

  Selective Cross-Couplings. Sequential Stille−Liebeskind/Srogl Reactions of 3-Chloro-4-arylthiocyclobutene-1,2-dione

  摘要：

  The synthesis and initial reactivity studies of 2 are described. It was found that it participates in Stille couplings exclusively at the C-Cl site with a number of organostannanes (58-71% yield) in the absence of Cu(I). Then, these new derivatives were functionalized at the C-S site with boronic acids by switching to the Liebeskind-Srogi reaction conditions (in the presence of a Cu(l) carboxylate) to yield the bifunctionalized cyclobutenediones (44-90% yield).

  DOI：

  10.1021/ol701628z
• 作为产物：
  描述：

  4-甲氧基苯硫酚 在 双(乙腈)氯化钯(II) 三乙胺 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 7.0h， 生成 3-(4-Methoxyphenyl)sulfanyl-4-(4-methylphenyl)cyclobut-3-ene-1,2-dione
  参考文献：
  名称：

  Selective Cross-Couplings. Sequential Stille−Liebeskind/Srogl Reactions of 3-Chloro-4-arylthiocyclobutene-1,2-dione

  摘要：

  The synthesis and initial reactivity studies of 2 are described. It was found that it participates in Stille couplings exclusively at the C-Cl site with a number of organostannanes (58-71% yield) in the absence of Cu(I). Then, these new derivatives were functionalized at the C-S site with boronic acids by switching to the Liebeskind-Srogi reaction conditions (in the presence of a Cu(l) carboxylate) to yield the bifunctionalized cyclobutenediones (44-90% yield).

  DOI：

  10.1021/ol701628z

文献信息

• 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).