3-n-butyl-2-[(trimethylsilyl)ethynyl]thiophene | 187791-43-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 3-n-butyl-2-[(trimethylsilyl)ethynyl]thiophene
• 英文别名: 2-(3-Butylthiophen-2-yl)ethynyl-trimethylsilane
• CAS: 187791-43-1
• 化学式: C₁₃H₂₀SSi
• 分子量: 236.453
• InChiKey: CJZMJGOPACIPAQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.32
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  28.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-n-butyl-2-[(trimethylsilyl)ethynyl]thiophene 在 碘 、 二异丙胺 、 lithium diisopropyl amide 作用下， 以 乙醚 、 正己烷 为溶剂， 以93%的产率得到5-iodo-3-n-butyl-2-[(trimethylsilyl)ethynyl]thiophene
  参考文献：
  名称：

  单分散低聚[（1,4-亚苯基亚乙炔基）-alt-（2,5-噻吩亚乙炔基）] s的快速溶液和固相合成

  摘要：

  单分散低聚物[（1,4-亚苯基亚乙炔基）-alt-（2,5-噻吩亚乙炔基）]是分子线的新候选物，通过在溶液中以及在Merrifield树脂上的迭代发散/会聚倍增策略快速合成。

  DOI：

  10.1016/j.tet.2005.12.043
• 作为产物：
  描述：

  3-丁基噻吩 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 碘 、 mercury(II) oxide 作用下， 生成 3-n-butyl-2-[(trimethylsilyl)ethynyl]thiophene
  参考文献：
  名称：

  单分散低聚[（1,4-亚苯基亚乙炔基）-alt-（2,5-噻吩亚乙炔基）] s的快速溶液和固相合成

  摘要：

  单分散低聚物[（1,4-亚苯基亚乙炔基）-alt-（2,5-噻吩亚乙炔基）]是分子线的新候选物，通过在溶液中以及在Merrifield树脂上的迭代发散/会聚倍增策略快速合成。

  DOI：

  10.1016/j.tet.2005.12.043

文献信息

• Synthesis of Monodisperse Oligo[(1,4‐Phenyleneethynylene)‐Alt‐(2,5‐Thiopheneethynylene)]s
  作者：Guorong Li、Xianhong Wang、Ji Li、Xiaojiang Zhao、Fosong Wang

  DOI：10.1081/scc-200046517

  日期：2005.1.1

  Abstract The synthesis of monodisperse oligo[(1,4‐phenyleneethynylene)‐alt‐(2,5‐thioph‐eneethynylene)]s using an iterative divergent/convergent doubling strategy based on Sonogashira coupling reaction was presented.

  摘要 提出了使用基于 Sonogashira 偶联反应的迭代发散/收敛倍增策略合成单分散低聚 [(1,4-亚苯基乙炔基)-alt-(2,5-噻吩-亚乙炔基)]s。
• Regioregular Poly[2,5-bis(3-butyl-2-thienyl)tellurophene]: Synthesis and Characterization Aspects
  作者：S. C. Ng、H. Ding、H. S. O. Chan

  DOI：10.1246/cl.1999.1325

  日期：1999.12

  methodology into the tellurophene nucleus, which was applied in particular to the synthesis of the centrosymmetrical 2,5-bis(3-butyl-2-thienyl)tellurophene. Thereafter, oxidative polymerization of the monomer using iron (III) chloride afforded the regioregular poly[2,5-bis(3-butyl-2-thienyl)tellurophene]. Preliminary characterization aspects of the polymer are reported.

  这项工作报告了一种新型、简便的碲酚核合成方法，该方法特别适用于合成中心对称的 2,5-双（3-丁基-2-噻吩基）碲酚。此后，使用氯化铁 (III) 对单体进行氧化聚合，得到区域规则的聚 [2,5-双 (3-丁基-2-噻吩基) 碲苯]。报告了聚合物的初步表征方面。
• Rapid Syntheses of Oligo(2,5-thiophene ethynylene)s with Thioester Termini:  Potential Molecular Scale Wires with Alligator Clips
  作者：Darren L. Pearson、James M. Tour

  DOI：10.1021/jo962335y

  日期：1997.3.1

  The syntheses of soluble oligo(3-ethyl-2,5-thiophene ethynylene)s via an iterative divergent/convergent approach starting from 3-ethyl-2-(trimethylsilylethynyl)thiophene are described. The monomer, dimer, tetramer, octamer, and 16-mer were synthesized. The 16-mer is 100 Angstrom long in its minimized extended zigzag conformation. At each stage in the iteration, the length of the framework doubles. Only three sets of reaction conditions are needed for the entire iterative synthetic sequence: an iodination, a protodesilylation, and a Pd/Cu-catalyzed cross coupling. The oligomers were characterized spectroscopically and by mass spectrometry. The optical properties are presented which show that at the octamer stage, the optical absorbance maximum is nearly saturated. The size exclusion chromatography values for the number average weights, relative to polystyrene, illustrate the tremendous differences in the hydrodynamic volume of these rigid rod oligomers verses the random coils of polystyrene. These differences become quite apparent at the octamer stage. Attachment of thiol end groups, protected as the thioacetyl moieties, was achieved. These serve as binding sites for adhesion to gold surfaces. In some cases, one end of the oligomeric chains were capped with a thiol group so that the surface attachments to gold could be studied. In other cases, thiol groups were affixed to both ends of the molecular chains so that future conduction studies could be done between proximal metallic probes. The rigid rod conjugated oligomers may act as molecular wires in molecular scale electronic devices, and they also serve as useful models for understanding analogous bulk polymers.