3',4',3'''',4''''-tetrabutyl-5,5'''''-dimethyl-2,2':5',2'':5'',2''':5''',2'''':5'''',2'''''-sexithiophene | 416845-06-2

• 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'''',4''''-tetrabutyl-5,5'''''-dimethyl-2,2':5',2'':5'',2''':5''',2'''':5'''',2'''''-sexithiophene
• 英文别名: 3,4-Dibutyl-2-[5-[5-[3,4-dibutyl-5-(5-methylthiophen-2-yl)thiophen-2-yl]thiophen-2-yl]thiophen-2-yl]-5-(5-methylthiophen-2-yl)thiophene
• CAS: 416845-06-2
• 化学式: C₄₂H₅₀S₆
• 分子量: 747.255
• InChiKey: MYDRBFJRHKWFRU-UHFFFAOYSA-N

物化性质

• 沸点：
  740.7±60.0 °C(predicted)
• 密度：
  1.152±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  16.8
• 重原子数：
  48
• 可旋转键数：
  17
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  169
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3',4',3'''',4''''-tetrabutyl-5,5'''''-dimethyl-2,2':5',2'':5'',2''':5''',2'''':5'''',2'''''-sexithiophene 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以35.8%的产率得到3,4-Dibutyl-2-[5-[5-[3,4-dibutyl-5-(5-methylthiophen-2-yl)-1,1-dioxothiophen-2-yl]thiophen-2-yl]thiophen-2-yl]-5-(5-methylthiophen-2-yl)thiophene 1,1-dioxide
  参考文献：
  名称：

  Reverse Selectivity in m-CPBA Oxidation of Oligothiophenes to Sulfones

  摘要：

  Oligothiophene sulfones of up to six rings can be conveniently prepared by the direct oxidation of butyl-substituted thiophene oligomers with m-CPBA in dichloromethane. Reverse selectivity of oxidized rings is observed relative to previously reported systems without beta-substitution. The selectivity in the trimer and hexamer is confirmed with single-crystal X-ray structure data. The sulfones possess red-shifted absorptions and increased electron affinities relative to the parent oligomers.

  DOI：

  10.1021/ol071369x
• 作为产物：
  描述：

  3,4-二丁基-2,5-二噻吩-2-基噻吩 在 氢氧化钾 、 N-溴代丁二酰亚胺(NBS) 、 正丁基锂 、 一水合肼 、 三氯氧磷 作用下， 以 四氢呋喃 、 正己烷 、 氯仿 、 溶剂黄146 、 1,2-二氯乙烷 、 丙酮 、 正丁醇 为溶剂， 反应 49.5h， 生成 3',4',3'''',4''''-tetrabutyl-5,5'''''-dimethyl-2,2':5',2'':5'',2''':5''',2'''':5'''',2'''''-sexithiophene
  参考文献：
  名称：

  Reverse Selectivity in m-CPBA Oxidation of Oligothiophenes to Sulfones

  摘要：

  Oligothiophene sulfones of up to six rings can be conveniently prepared by the direct oxidation of butyl-substituted thiophene oligomers with m-CPBA in dichloromethane. Reverse selectivity of oxidized rings is observed relative to previously reported systems without beta-substitution. The selectivity in the trimer and hexamer is confirmed with single-crystal X-ray structure data. The sulfones possess red-shifted absorptions and increased electron affinities relative to the parent oligomers.

  DOI：

  10.1021/ol071369x

文献信息

• Reverse Selectivity in <i>m</i>-CPBA Oxidation of Oligothiophenes to Sulfones
  作者：Ted M. Pappenfus、Jacob H. Melby、Brent B. Hansen、Devin M. Sumption、Scott A. Hubers、Daron E. Janzen、Paul C. Ewbank、Kari A. McGee、Michael W. Burand、Kent R. Mann

  DOI：10.1021/ol071369x

  日期：2007.9.1

  Oligothiophene sulfones of up to six rings can be conveniently prepared by the direct oxidation of butyl-substituted thiophene oligomers with m-CPBA in dichloromethane. Reverse selectivity of oxidized rings is observed relative to previously reported systems without beta-substitution. The selectivity in the trimer and hexamer is confirmed with single-crystal X-ray structure data. The sulfones possess red-shifted absorptions and increased electron affinities relative to the parent oligomers.