tetraethyl benzo[b]thiophene-4,5,6,7-tetracarboxylate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: tetraethyl benzo[b]thiophene-4,5,6,7-tetracarboxylate
• 英文别名: Tetraethyl 1-benzothiophene-4,5,6,7-tetracarboxylate
• 化学式: C₂₀H₂₂O₈S
• 分子量: 422.456
• InChiKey: OUCVKGKQTIJSTN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  29
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  133
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  sodium thiophene-2-sulfinate 、 丁炔二酸二乙酯 在 dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer 、 silver(I) acetate 、 溶剂黄146 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 36.0h， 以52%的产率得到tetraethyl benzo[b]thiophene-4,5,6,7-tetracarboxylate
  参考文献：
  名称：

  铑催化的芳烃次磺酸钠的脱硫和炔烃的氧化环化

  摘要：

  AbstractPolycyclic aromatic compounds are widely used in materials science, so it is highly desirable to develop an efficient and practical approach to them. In this paper, a novel, efficient and practical method for the rhodium(III)‐catalyzed desulfination of sodium arenesulfinates and oxidative annulation with alkynes has been developed, and the corresponding polycyclic aromatic compounds with multiple substituents were prepared in moderate to good yields. The reactions proceeded through sequential rhodium(III)‐catalyzed desulfination, intermolecular addition of aryl‐Rh(III) complexes to dialkyl but‐2‐ynedioates and diarylalkynes, and intramolecular oxidative annulation via CH activation. The present method is the first example of the oxidative annulation of arene derivatives with two different alkynes. Therefore, it should afford a useful strategy for the synthesis of polycyclic aromatic compounds.magnified image

  DOI：

  10.1002/adsc.201400930

文献信息

• Synthesis of Tetrasubstituted Naphthalenes by Palladium-Catalyzed Reaction of Aryl Iodides with Internal Alkynes
  作者：Satoshi Kawasaki、Tetsuya Satoh、Masahiro Miura、Masakatsu Nomura

  DOI：10.1021/jo0346656

  日期：2003.8.1

  acetylenedicarboxylate esters and diphenylacetylene efficiently proceeds in the presence of a palladium catalyst with use of silver carbonate as base to produce the corresponding tetrasubstituted naphthalenes.

  在钯催化剂存在下，以碳酸银为碱，芳基碘化物与乙炔二羧酸酯和二苯乙炔的1：2偶联有效地进行，以产生相应的四取代萘。