3-iodo-4-(trimethylsilylethynyl)pyridine | 596093-47-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 3-iodo-4-(trimethylsilylethynyl)pyridine
• 英文别名: 4-trimethylsilylethynyl-3-iodopyridine；2-(3-Iodopyridin-4-yl)ethynyl-trimethylsilane；2-(3-iodopyridin-4-yl)ethynyl-trimethylsilane
• CAS: 596093-47-9
• 化学式: C₁₀H₁₂INSi
• 分子量: 301.202
• InChiKey: PTGULMNPZRGKLX-UHFFFAOYSA-N

物化性质

• 沸点：
  287.7±40.0 °C(Predicted)
• 密度：
  1.47±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.92
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-iodo-4-(trimethylsilylethynyl)pyridine 在 四丁基氟化铵 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 14.0h， 以91%的产率得到3-iodo-4-ethynylpyridine
  参考文献：
  名称：

  Nitrogen Heterocyclic Carbon-Rich Materials:  Synthesis and Spectroscopic Properties of Dehydropyridoannulene Macrocycles

  摘要：

  A new series of nitrogen heterocyclic dehydroannulenes 1-3 have been synthesized and their macrocyclic structures assigned using spectroscopic methods. The chiral and planar ground state conformations of 1 and 3, respectively, were determined by semiempirical theoretical calculations. All dehydropyridoannulenes and precursors possessing four aromatic rings functioned as fluorescent chromophores. A detailed spectroscopic investigation into the cation-binding properties of 3 in dilute solution revealed a particularly selective photoluminescence quenching sensory response for Pd-II ions. Cycle 3, as well as 1 and 2, also exhibited reversible proton-triggered luminescence quenching behavior. At higher concentrations, 3 afforded a coordination polymer precipitate with Ag-I ions. Cycles I and 2 and precursors 15, 23, and 29 also undergo thermochemical reactions that may potentially lead to carbon-rich polymers. The physicochemical properties of 1-3 suggest that dehydropyridoarmulenes may serve as a particularly versatile new class of ligands for the creation of novel heteroatom-containing carbon-rich materials with many potential applications in supramolecular materials science and nanotechnology.

  DOI：

  10.1021/jo040276f
• 作为产物：
  描述：

  3-溴-4-碘吡啶 在 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 、 正丁基锂 、 三乙胺 作用下， 以 乙醚 、 正己烷 为溶剂， 反应 171.5h， 生成 3-iodo-4-(trimethylsilylethynyl)pyridine
  参考文献：
  名称：

  具有强制的外位金属离子结合位点的第一个脱氢吡啶环戊二烯型环烷的合成和荧光离子传感性能。

  摘要：

  已经合成了新的扭索烷4，其包含具有向外突出的氮供体位点的共轭脱氢吡啶并环戊烯型大环骨架，用于金属离子配位。使用光谱学方法对4的大环结构进行了分配，并通过半经验理论计算表明其以扭曲和手性的基态构象存在。对4和前体11的金属离子结合特性进行的详细光谱研究表明，它们起选择性配位剂的作用，提供了Pd（II）和Hg（II）离子的荧光猝灭输出响应特性。此外，4还通过配位聚合物的沉淀表明存在Fe（II），Co（II），Ni（II）和Ag（I）离子，并表现出可逆的质子触发的荧光猝灭行为。

  DOI：

  10.1002/chem.2003044561

文献信息

• Cyclic Donor−Acceptor Circuits:  Synthesis and Fluorescence Ion Sensory Properties of a Mixed-Heterocyclic Dehydroannulene-Type Cyclophane
  作者：Paul N. W. Baxter

  DOI：10.1021/jo0302410

  日期：2004.3.1

  thiophene (electron donor) and pyridine (electron acceptor) heterocyclic units has been prepared. Macrocycle 5 was characterized by FAB MS and 1H and 13C NMR spectroscopy. Cycle 5 was found to function as a selective precipitation and fluorescence sensor for specific metal ions such as AgI and also exhibited reversible proton-triggered fluorescence quenching behavior. The unique donor−acceptor architecture

  新dehydroannulene型环芳5包括噻吩（电子供体）的共轭螺旋框架和吡啶（电子受体）杂环单元已被制备。大环5通过FAB MS以及1 H和13 C NMR光谱法表征。发现周期5充当特定金属离子（例如Ag I）的选择性沉淀和荧光传感器，并且还表现出可逆的质子触发的荧光猝灭行为。独特的供体-受体结构和光谱性质5 这表明它代表了分子传感平台的新型领导者，在21世纪材料科学中具有许多潜在的未来应用。
• Nitrogen Heterocyclic Carbon-Rich Materials:  Synthesis and Spectroscopic Properties of Dehydropyridoannulene Macrocycles
  作者：Paul N. W. Baxter、Riad Dali-Youcef

  DOI：10.1021/jo040276f

  日期：2005.6.1

  A new series of nitrogen heterocyclic dehydroannulenes 1-3 have been synthesized and their macrocyclic structures assigned using spectroscopic methods. The chiral and planar ground state conformations of 1 and 3, respectively, were determined by semiempirical theoretical calculations. All dehydropyridoannulenes and precursors possessing four aromatic rings functioned as fluorescent chromophores. A detailed spectroscopic investigation into the cation-binding properties of 3 in dilute solution revealed a particularly selective photoluminescence quenching sensory response for Pd-II ions. Cycle 3, as well as 1 and 2, also exhibited reversible proton-triggered luminescence quenching behavior. At higher concentrations, 3 afforded a coordination polymer precipitate with Ag-I ions. Cycles I and 2 and precursors 15, 23, and 29 also undergo thermochemical reactions that may potentially lead to carbon-rich polymers. The physicochemical properties of 1-3 suggest that dehydropyridoarmulenes may serve as a particularly versatile new class of ligands for the creation of novel heteroatom-containing carbon-rich materials with many potential applications in supramolecular materials science and nanotechnology.
• Synthesis and Fluorescence Ion-Sensory Properties of the First Dehydropyridoannulene-Type Cyclophane with Enforced Exotopic Metal Ion Binding Sites
  作者：Paul. N. W. Baxter

  DOI：10.1002/chem.2003044561

  日期：2003.6.6

  dehydropyridoannulene-type macrocyclic scaffold with outwardly projecting nitrogen-donor sites for the purpose of metal ion coordination. The macrocyclic structure of 4 was assigned by using spectroscopic methods, and shown to exist in a twisted and chiral ground state conformation by semi-empirical theoretical calculations. A detailed spectroscopic investigation into the metal ion binding properties of 4 and precursor

  已经合成了新的扭索烷4，其包含具有向外突出的氮供体位点的共轭脱氢吡啶并环戊烯型大环骨架，用于金属离子配位。使用光谱学方法对4的大环结构进行了分配，并通过半经验理论计算表明其以扭曲和手性的基态构象存在。对4和前体11的金属离子结合特性进行的详细光谱研究表明，它们起选择性配位剂的作用，提供了Pd（II）和Hg（II）离子的荧光猝灭输出响应特性。此外，4还通过配位聚合物的沉淀表明存在Fe（II），Co（II），Ni（II）和Ag（I）离子，并表现出可逆的质子触发的荧光猝灭行为。