3,3'''-Dimethoxy-2,2':5',2'':5'',2'''-quaterthiophene | 168845-53-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 双噻吩和低聚噻吩
• 英文名称: 3,3'''-Dimethoxy-2,2':5',2'':5'',2'''-quaterthiophene
• 英文别名: 2-(3-Methoxythiophen-2-yl)-5-[5-(3-methoxythiophen-2-yl)thiophen-2-yl]thiophene
• CAS: 168845-53-2
• 化学式: C₁₈H₁₄O₂S₄
• 分子量: 390.572
• InChiKey: PETZQKOZUUNNIU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  131
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  硫酸二甲酯 、 3,3'''-Dimethoxy-2,2':5',2'':5'',2'''-quaterthiophene 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 以85%的产率得到3,3'''-Dimethoxy-5,5'''-dimethyl-2,2':5',2'':5'',2'''-quaterthiophene
  参考文献：
  名称：

  Synthesis of .beta.-Methoxy, Methyl-Capped .alpha.-Oligothiophenes

  摘要：

  The first syntheses of structurally defined methoxyoligothiophenes are described. Nine alpha-coupled oligothiophenes, dimers through hexamers, symmetrically substituted at the ''inside'' or ''outside'' beta-positions with two or four methoxy groups, and with terminal methyl groups, were prepared. The electron-donor methoxy groups and terminal methyls have been shown to stabilize cationic species formed by oxidation or protonation of these oligomers. The oligomers were built up by the cross coupling of(mono- or oligo-) beta-methoxy-alpha-iodothiophenes and (mono- or oligo-) alpha-stannylthiophenes catalyzed by Pd(0)/Pd(ll) or by the redox home-coupling of alpha-thienyllithium compounds with Fe(acac)(3). Synthesis by the cross coupling of thienyl Grignard reagents and bromothiophenes with Ni(0) or Suzuki coupling using organoboranes was not successful. An X-ray crystal structure of a dimethoxy quaterthiophene is reported.

  DOI：

  10.1021/jo00126a034
• 作为产物：
  描述：

  3-甲氧基噻吩 在 四(三苯基膦)钯 、 正丁基锂 、 三丁基氯化锡 、 碘 、 mercury(II) oxide 作用下， 以 苯 为溶剂， 反应 1.5h， 生成 3,3'''-Dimethoxy-2,2':5',2'':5'',2'''-quaterthiophene
  参考文献：
  名称：

  Synthesis of .beta.-Methoxy, Methyl-Capped .alpha.-Oligothiophenes

  摘要：

  The first syntheses of structurally defined methoxyoligothiophenes are described. Nine alpha-coupled oligothiophenes, dimers through hexamers, symmetrically substituted at the ''inside'' or ''outside'' beta-positions with two or four methoxy groups, and with terminal methyl groups, were prepared. The electron-donor methoxy groups and terminal methyls have been shown to stabilize cationic species formed by oxidation or protonation of these oligomers. The oligomers were built up by the cross coupling of(mono- or oligo-) beta-methoxy-alpha-iodothiophenes and (mono- or oligo-) alpha-stannylthiophenes catalyzed by Pd(0)/Pd(ll) or by the redox home-coupling of alpha-thienyllithium compounds with Fe(acac)(3). Synthesis by the cross coupling of thienyl Grignard reagents and bromothiophenes with Ni(0) or Suzuki coupling using organoboranes was not successful. An X-ray crystal structure of a dimethoxy quaterthiophene is reported.

  DOI：

  10.1021/jo00126a034

文献信息

• Direct C–H arylation of 3-methoxythiophene catalyzed by Pd. Application to a more efficient synthesis of π-alkoxy-oligothiophene derivatives
  作者：A. Borghese、G. Geldhof、L. Antoine

  DOI：10.1016/j.tetlet.2006.10.130

  日期：2006.12

  The direct regioselective C-H arylation of 3-methoxythiophene and 3,4-ethylenedioxythiophene (EDOT) was performed successfully under 'Heck-type' experimental conditions. This novel synthetic methodology has been used to prepare in a more simple way a series of oligothiophenes interesting for the electronic industry to build new synthetic organic materials. (c) 2006 Elsevier Ltd. All rights reserved.
• Synthesis of .beta.-Methoxy, Methyl-Capped .alpha.-Oligothiophenes
  作者：Larry L. Miller、Yuan Yu

  DOI：10.1021/jo00126a034

  日期：1995.10

  The first syntheses of structurally defined methoxyoligothiophenes are described. Nine alpha-coupled oligothiophenes, dimers through hexamers, symmetrically substituted at the ''inside'' or ''outside'' beta-positions with two or four methoxy groups, and with terminal methyl groups, were prepared. The electron-donor methoxy groups and terminal methyls have been shown to stabilize cationic species formed by oxidation or protonation of these oligomers. The oligomers were built up by the cross coupling of(mono- or oligo-) beta-methoxy-alpha-iodothiophenes and (mono- or oligo-) alpha-stannylthiophenes catalyzed by Pd(0)/Pd(ll) or by the redox home-coupling of alpha-thienyllithium compounds with Fe(acac)(3). Synthesis by the cross coupling of thienyl Grignard reagents and bromothiophenes with Ni(0) or Suzuki coupling using organoboranes was not successful. An X-ray crystal structure of a dimethoxy quaterthiophene is reported.