3,4',3''',3''''-Tetramethoxy-2,2':5',2'':5'',2''':5''',2''''-quinquethiophene | 171917-41-2

• 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: 3,4',3''',3''''-Tetramethoxy-2,2':5',2'':5'',2''':5''',2''''-quinquethiophene
• 英文别名: 3-Methoxy-2-[5-[3-methoxy-5-(3-methoxythiophen-2-yl)thiophen-2-yl]thiophen-2-yl]-5-(3-methoxythiophen-2-yl)thiophene
• CAS: 171917-41-2
• 化学式: C₂₄H₂₀O₄S₅
• 分子量: 532.75
• InChiKey: CXSAQGZABSOGLF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  33
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  178
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  硫酸二甲酯 、 3,4',3''',3''''-Tetramethoxy-2,2':5',2'':5'',2''':5''',2''''-quinquethiophene 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 以80%的产率得到3,4',3''',3''''-Tetramethoxy-5,5''''-dimethyl-2,2':5',2'':5'',2''':5''',2''''-quinquethiophene
  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：

  2-碘-3-甲氧基噻吩 在 bis-triphenylphosphine-palladium(II) chloride 、 四(三苯基膦)钯 、 正丁基锂 、 三丁基氯化锡 作用下， 以 甲苯 为溶剂， 反应 49.0h， 生成 3,4',3''',3''''-Tetramethoxy-2,2':5',2'':5'',2''':5''',2''''-quinquethiophene
  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

• 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.