1,2-dihexyl-4,5-bis(trimethylsilylethynyl)benzene | 155259-03-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,2-dihexyl-4,5-bis(trimethylsilylethynyl)benzene
• 英文别名: 4,5-dihexyl-1,2-bis((trimethylsilyl)ethynyl)benzene；2-[4,5-Dihexyl-2-(2-trimethylsilylethynyl)phenyl]ethynyl-trimethylsilane
• CAS: 155259-03-3
• 化学式: C₂₈H₄₆Si₂
• 分子量: 438.844
• InChiKey: HYIFMITURQHSJB-UHFFFAOYSA-N

物化性质

• 沸点：
  475.2±45.0 °C(Predicted)
• 密度：
  0.90±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.39
• 重原子数：
  30
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1,2-dihexyl-4,5-bis(trimethylsilylethynyl)benzene 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 1,2-diethynyl-4,5-dihexylbenzene
  参考文献：
  名称：

  Synthesis of a Trinuclear Tropolone–Palladium(II) Macrocycle and Its C₆₀ Inclusion Properties

  摘要：

  合成了4,5-二烷基-1,2-双(5-环丙炔基乙炔基)苯5a和5b，二辛基衍生物5a通过与Pd(OAc)2反应转化为相应的三核钯(II)大环1a。大环超分子配位络合物1a的内腔刚好足以容纳C60。尽管三核钯配合物1a由于双(托波罗)钯(II)部分与C60之间的弱相互作用而在溶液中不完全结合C60，但它在固态下与C60形成了包合物。包合物在紫外-可见-近红外光谱中显示出中等的电荷转移吸收。

  DOI：

  10.1246/cl.140638
• 作为产物：
  描述：

  邻二氯苯 在 bis-triphenylphosphine-palladium(II) chloride 、 bis(triphenylphosphine)nickel(II) chloride copper(l) iodide 、 sodium iodate 、 硫酸 、 碘 、 magnesium 、 二异丙胺 作用下， 以 溶剂黄146 为溶剂， 反应 1.5h， 生成 1,2-dihexyl-4,5-bis(trimethylsilylethynyl)benzene
  参考文献：
  名称：

  Synthesis of Diacetylene Macrocycles Derived from 1,2-Diethynyl Benzene Derivatives: Structure and Reactivity of the Strained Cyclic Dimer

  摘要：

  Diacetylene macrocycles 2-4 (n = 1-3) (R = H, C4H9, C6H13, C10H21, C12H25, OC10H21) have been prepared from the oxidative coupling of 1,2-diethynylbenzene derivatives. These compounds can be produced in useful quantities and are of interest as precursors to novel conjugated organic polymers. The reported results indicate that when the R groups are large the dimeric macrocycle (n = 1) can be prepared in as high as 74% yield from the corresponding 1,2-diethynylbenzene in a one-step procedure. An alternate multistep procedure was found to produce the tetrameric macrocycle (n = 3, R = C6H13) in 45 % yield. The highly strained dimeric macrocycle was characterized by an X-ray structure and was found to be very reactive. The dimers undergo a rapid very exothermic polymerization at 100-125-degrees-C, indicative of a chain reaction. Reaction of the dimeric macrocycles with iodine results in intramolecular cyclization and a new 20pi electron tetraiodide fused ring system. Reaction of the tetraiodide with oxygen produces a related compound in which two of the iodides have been converted to ketones.

  DOI：

  10.1021/jo00085a016

文献信息

• The Bergman reaction as a synthetic tool: advantages and restrictions
  作者：Daniel M Bowles、Grant J Palmer、Chad A Landis、John L Scott、John E Anthony

  DOI：10.1016/s0040-4020(01)00247-2

  日期：2001.4

  The Bergman cycloaromatization reaction efficiently converts easily prepared acyclic enediynes into aromatic rings. In order to prepare larger, functionalized fused aromatic systems using this reaction, a thorough understanding of how functionalization affects cycloaromatization is necessary. We present here our studies on the influence of substituents at three different functionalization sites on

  Bergman环芳烃化反应可有效地将易于制备的无环烯二炔转化为芳环。为了使用该反应制备更大的官能化稠合芳族体系，必须全面了解官能化如何影响环芳构化。在这里，我们介绍了三个不同功能化位点上取代基对环芳构化的影响以及如何对这些官能团进行定制以制备更复杂的系统的研究。
• Tellurium-Mediated Cycloaromatization of Acyclic Enediynes under Mild Conditions
  作者：Chad A. Landis、Marcia M. Payne、David L. Eaton、John E. Anthony

  DOI：10.1021/ja0389467

  日期：2004.2.1

  cycloaromatization product. We have developed conditions that form sodium telluride from inexpensive tellurium metal in situ, and that also perform the desilylation of silylated arenediynes in the same process. Under our conditions, we are able to perform desilylation and cycloaromatization at temperatures as low as 40 degrees C and on a scale as large as 5 g in standard laboratory glassware.

  无环烯二炔的环芳构化通常需要非常高的温度（> 160 摄氏度）和稀释条件才能以合成有用的产率进行。这些条件阻碍了反应产量，抑制了该反应在材料的大规模生产中的应用。碲化钠与无环芳二炔反应生成相应的碲碱，在温和加热下会挤出 Te 度，生成环芳构化产物。我们已经开发出从廉价的碲金属原位形成碲化钠的条件，并在同一过程中对甲硅烷基化芳烃进行脱甲硅烷基化。在我们的条件下，我们能够在低至 40 摄氏度的温度和大至 5 克的标准实验室玻璃器皿中进行脱甲硅烷基化和环芳构化。
• Cyclic and macrocyclic molecules containing silicon or tin – synthesis of highly rigid potentially Lewis‐acidic cryptands
  作者：Niklas Aders、Jan-Hendrik Lamm、Katharina Wels、Sophie Bernhardt、Beate Neumann、Hans-Georg Stammler、Norbert Werner Mitzel

  DOI：10.1002/ejic.202300061

  日期：——

  Highly rigid silicon- and tin-containing macrocyclic and bicyclic cage compounds with diethynylbenzene backbones were synthesized and characterized and their potential as Lewis acids was explored.

  合成并表征了具有二乙炔基苯骨架的高刚性含硅和含锡大环和双环笼化合物，并探索了它们作为路易斯酸的潜力。
• Zhou Qin, Carroll Patrick J., Swager Timothy M., J. Org. Chem., 59 (1994) N 6, S 1294-1301
  作者：Zhou Qin, Carroll Patrick J., Swager Timothy M.

  DOI：——

  日期：——