1,2-didodecyl-4,5-diethynylbenzene | 155259-32-8

• 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-didodecyl-4,5-diethynylbenzene
• CAS: 155259-32-8
• 化学式: C₃₄H₅₄
• 分子量: 462.803
• InChiKey: AAEPVUBNYWQLBI-UHFFFAOYSA-N

物化性质

• 沸点：
  552.5±50.0 °C(predicted)
• 密度：
  0.90±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  14.8
• 重原子数：
  34
• 可旋转键数：
  24
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 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-didodecyl-4,5-diethynylbenzene 以15%的产率得到
  参考文献：
  名称：

  Zhou Qin, Carroll Patrick J., Swager Timothy M., J. Org. Chem., 59 (1994) N 6, S 1294-1301

  摘要：

  DOI：
• 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-didodecyl-4,5-diethynylbenzene
  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