1,2-diethynyl-4,5-dihexylbenzene | 155259-27-1

• 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-diethynyl-4,5-dihexylbenzene
• 英文别名: 4,5-dihexyl-1,2-diethynylbenzene；1,2-dihexyl-4,5-bis(ethynyl)benzene
• CAS: 155259-27-1
• 化学式: C₂₂H₃₀
• 分子量: 294.48
• InChiKey: GRQUYKATGDIMOL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  22
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 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-diethynyl-4,5-dihexylbenzene 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 Oxone 、 N-溴代丁二酰亚胺(NBS) 、 正丁基锂 、 carbon monoxide,cobalt,cyclopenta-1,3-diene 、 碳酸氢钠 、 silver nitrate 、 N,N-二异丙基乙胺 、 cesium fluoride 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 水 、 丙酮 、 乙腈 为溶剂， 反应 28.5h， 生成 2,3-Dihexyl-benzo[b]biphenylene-6,7,8,9-tetracarboxylic acid tetramethyl ester
  参考文献：
  名称：

  三（苯并环丁二烯）三亚苯基及其低级联苯的同系物，通过钯催化2,3-二氢联苯的环化反应而形成。

  摘要：

  [反应：参见正文]由相应的3-（三甲基甲硅烷基）-2-联苯苯基三氟甲酸酯与氟化物生成的Pd催化的二氢联苯撑2a，b的环加成反应提供了C3对称三聚体1a，b，其中嵌入的三联苯单元为扭曲以增加中心苯环的芳香性。2a，b与乙炔基二羧酸二甲酯的共环化可提供菲-和萘甲酸酯类似物，具体取决于所用的催化剂。

  DOI：

  10.1021/ol048548o
• 作为产物：
  描述：

  邻二氯苯 在 bis-triphenylphosphine-palladium(II) chloride 、 bis(triphenylphosphine)nickel(II) chloride 氢氧化钾 、 copper(l) iodide 、 sodium iodate 、 硫酸 、 碘 、 magnesium 、 二异丙胺 作用下， 以 四氢呋喃 、 甲醇 、 溶剂黄146 为溶剂， 反应 1.5h， 生成 1,2-diethynyl-4,5-dihexylbenzene
  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。
• Synthesis of a Trinuclear Tropolone–Palladium(II) Macrocycle and Its C₆₀ Inclusion Properties
  作者：Hiroyuki Otani、Chisaki Sumi、Hideyuki Shimizu、Masashi Hasegawa、Masahiko Iyoda

  DOI：10.1246/cl.140638

  日期：2014.11.5

  4,5-Dialkyl-1,2-bis(5-tropolonylethynyl)benzenes 5a and 5b were synthesized, and dioctyl derivative 5a was converted into the corresponding trinuclear palladium(II) macrocycle 1a by reacting it with Pd(OAc)2. Macrocyclic supramolecular coordination complex 1a has an inner cavity just large enough to include C60. Although trinuclear palladium complex 1a incompletely incorporated C60 in solution owing to weak interactions between the bis(tropolono)palladium(II) moieties and C60, it formed an inclusion complex with C60 in the solid state. The inclusion complex showed a moderate charge-transfer absorption in the UV–vis–NIR spectra.

  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。
• 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：——