5-phenyl-4-(thiophen-2-ylmethyl)-2,2′-bithiophene

• 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: 5-phenyl-4-(thiophen-2-ylmethyl)-2,2′-bithiophene
• 英文别名: 5'-Phenyl-4'-(2-thienylmethyl)-2,2'-bithiophene；Thiophene, 2-[(5-phenyl[2,2'-bithiophen]-4-yl)methyl]-；2-phenyl-5-thiophen-2-yl-3-(thiophen-2-ylmethyl)thiophene
• 化学式: C₁₉H₁₄S₃
• 分子量: 338.518
• InChiKey: RUTBNKNZOYSBDT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  84.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-三甲基硅乙炔基噻吩 在 potassium fluoride 、 potassium hydroxide 作用下， 以 二甲基亚砜 为溶剂， 反应 17.0h， 生成 5-phenyl-4-(thiophen-2-ylmethyl)-2,2′-bithiophene
  参考文献：
  名称：

  Pseudo Five-Component Synthesis of 3-(Hetero)arylmethyl-2,5-di(hetero)-aryl-Substituted Thiophenes via Sonogashira–Glaser Cyclization Sequence

  摘要：

  The Sonogashira-Glaser sequence combined with a microwave-assisted cyclization is a powerful tool to synthesize unsymmetrically substituted conjugated thiophenes. A variety of 3-(hetero)arylmethyl-2,5-di(hetero)aryl-substituted thiophenes could be synthesized in moderate to excellent yields using a single Pd/Cu catalyst system. The presented method is strikingly simple to perform using commercially available starting materials. The obtained trisubstituted oligothiophene derivatives are interesting molecules for materials science.

  DOI：

  10.1055/s-0034-1379074

文献信息

• Reactions of Arylmethanethiols with 1,4-Disubstituted 1,3-Butadiynes
  作者：Fillmore Freeman、Hengyao Lu、Qingbei Zeng、Eloy Rodriguez

  DOI：10.1021/jo00094a062

  日期：1994.7
• A novel synthesis of 2,5-diaryl-3-(phenylmethyl)thiophenes
  作者：Fillmore Freeman、Hengyao Lu、Eloy Rodriguez

  DOI：10.1016/s0040-4039(00)60770-0

  日期：1993.3

  Addition of phenylmethanethiols (benzylthiols), including (2-furyl)methanethiol, to butadiynes in potassium hydroxide/dimethyl sulfoxide affords the corresponding 2,5-diaryl-3-(phenylmethyl)thiophenes.
• Freeman Fillmore, Lu Hengyao, Zeng Qingbei, Rodriguez Eloy, J. Org. Chem, 59 (1994) N 15, S 4350-4354
  作者：Freeman Fillmore, Lu Hengyao, Zeng Qingbei, Rodriguez Eloy

  DOI：——

  日期：——
• Pseudo Five-Component Synthesis of 3-(Hetero)arylmethyl-2,5-di(hetero)-aryl-Substituted Thiophenes via Sonogashira–Glaser Cyclization Sequence
  作者：Thomas Müller、Fabian Klukas、Jörg Perkampus、Dominik Urselmann

  DOI：10.1055/s-0034-1379074

  日期：——

  The Sonogashira-Glaser sequence combined with a microwave-assisted cyclization is a powerful tool to synthesize unsymmetrically substituted conjugated thiophenes. A variety of 3-(hetero)arylmethyl-2,5-di(hetero)aryl-substituted thiophenes could be synthesized in moderate to excellent yields using a single Pd/Cu catalyst system. The presented method is strikingly simple to perform using commercially available starting materials. The obtained trisubstituted oligothiophene derivatives are interesting molecules for materials science.