2-[3,3',3''',4'''',3'''''-Pentakis-(2-hydroxy-ethyl)-[2,2';5',2'';5'',2''';5''',2'''';5'''',2''''']sexithiophen-4''-yl]-ethanol

• 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: 2-[3,3',3''',4'''',3'''''-Pentakis-(2-hydroxy-ethyl)-[2,2';5',2'';5'',2''';5''',2'''';5'''',2''''']sexithiophen-4''-yl]-ethanol
• 英文别名: 2-[2-[3-(2-Hydroxyethyl)-5-[4-(2-hydroxyethyl)-5-[3-(2-hydroxyethyl)-5-[4-(2-hydroxyethyl)-5-[3-(2-hydroxyethyl)thiophen-2-yl]thiophen-2-yl]thiophen-2-yl]thiophen-2-yl]thiophen-2-yl]thiophen-3-yl]ethanol
• 化学式: C₃₆H₃₈O₆S₆
• 分子量: 759.09
• InChiKey: FDBOCQYTXBDDQA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  48
• 可旋转键数：
  17
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  291
• 氢给体数：
  6
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  3,3',4'',3''',4'''',3'''''-hexakis[2-(tetrahydropyranyloxy)ethyl]-2,2':5',2'':5'',2''':5''',2'''':5'''',2'''''-sexithiophene 在 盐酸 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以73%的产率得到2-[3,3',3''',4'''',3'''''-Pentakis-(2-hydroxy-ethyl)-[2,2';5',2'';5'',2''';5''',2'''';5'''',2''''']sexithiophen-4''-yl]-ethanol
  参考文献：
  名称：

  Polyhydroxyoligothiophenes. 2. Hydrogen-Bonding-Oriented Solid State Conformation of 3,3‘-Bis(2-hydroxyethyl)-2,2‘-bithiophene and Regioselective Synthesis of the Corresponding Head-to-Head/Tail-to-Tail Quater- and Sexithiophene

  摘要：

  This paper reports the X-ray structure of 3,3'-bis(2-hydroxyethyl)-2,2'-bithiophene (1), which is the building block for the synthesis of head-to-head/tail-to-tail 2-hydroxyethyl-substituted oligothiophenes. Contrary to all the bithiophenes reported so far, 1 exhibits a noncoplanar anti conformation and an inter-ring twist angle (67.5 degrees) which is the largest ever measured for adjacent rings of a-conjugated oligothiophenes. This unusual conformation appears to be dictated by intermolecular hydrogen-bonding interactions involving the OH groups, which bind the molecule in close packed layers. The paper also describes the regioselective synthesis of the dimer and the trimer of 1, namely of 3,3',4 '',3 triple prime-tetrakis(2-hydroxyethyl)-2,2':5',2 '':5 '',2 triple prime-quaterthiophene (3c) and of 3,3',4 '',3 triple prime,4'''':3''''-hexakis(2-hydroxyethyl)-2':5',2 '': 5 '',2'''':5'''',2'''': 5'''',2''''-sexithiophene (4b). 3c And 4b were obtained through palladium(0)-catalyzed coupling of the mono- and distannanes of the tetrahydropyranyl derivative of 1 with the appropriate monobromo compound (Stille's reaction). Finally, the paper reports force-field calculations which suggest that the low lambda(max) values measured for 1, 3c, and 4b are also the result of intramolecular hydrogen-bonding interactions which favor highly twisted conformations in solution.

  DOI：

  10.1021/jo952278t

文献信息

• Polyhydroxyoligothiophenes. 2. Hydrogen-Bonding-Oriented Solid State Conformation of 3,3‘-Bis(2-hydroxyethyl)-2,2‘-bithiophene and Regioselective Synthesis of the Corresponding Head-to-Head/Tail-to-Tail Quater- and Sexithiophene
  作者：G. Barbarella、M. Zambianchi、A. Bongini、L. Antolini

  DOI：10.1021/jo952278t

  日期：1996.1.1

  This paper reports the X-ray structure of 3,3'-bis(2-hydroxyethyl)-2,2'-bithiophene (1), which is the building block for the synthesis of head-to-head/tail-to-tail 2-hydroxyethyl-substituted oligothiophenes. Contrary to all the bithiophenes reported so far, 1 exhibits a noncoplanar anti conformation and an inter-ring twist angle (67.5 degrees) which is the largest ever measured for adjacent rings of a-conjugated oligothiophenes. This unusual conformation appears to be dictated by intermolecular hydrogen-bonding interactions involving the OH groups, which bind the molecule in close packed layers. The paper also describes the regioselective synthesis of the dimer and the trimer of 1, namely of 3,3',4 '',3 triple prime-tetrakis(2-hydroxyethyl)-2,2':5',2 '':5 '',2 triple prime-quaterthiophene (3c) and of 3,3',4 '',3 triple prime,4'''':3''''-hexakis(2-hydroxyethyl)-2':5',2 '': 5 '',2'''':5'''',2'''': 5'''',2''''-sexithiophene (4b). 3c And 4b were obtained through palladium(0)-catalyzed coupling of the mono- and distannanes of the tetrahydropyranyl derivative of 1 with the appropriate monobromo compound (Stille's reaction). Finally, the paper reports force-field calculations which suggest that the low lambda(max) values measured for 1, 3c, and 4b are also the result of intramolecular hydrogen-bonding interactions which favor highly twisted conformations in solution.