1,2:7,8-di(4,5-didecyl)benzocyclododeca-1,7-diene-3,5,9,11-tetrayne | 154104-77-5

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: 1,2:7,8-di(4,5-didecyl)benzocyclododeca-1,7-diene-3,5,9,11-tetrayne
• CAS: 154104-77-5
• 化学式: C₆₀H₈₈
• 分子量: 809.359
• InChiKey: JZPZOPYQBVFGSO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  17.9
• 重原子数：
  60
• 可旋转键数：
  36
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  1,2:7,8-di(4,5-didecyl)benzocyclododeca-1,7-diene-3,5,9,11-tetrayne 在 碘 作用下， 以 苯 为溶剂， 生成 2,3,8,9-Tetrakis-decyl-5,6,11,12-tetraiodo-indeno[1,2-b]fluorene
  参考文献：
  名称：

  茚并[1,2-b]芴：共轭共芳烃的芳烃类似物

  摘要：

  如果什么？通过通常用于生成乙炔的SnCl 2促进的还原反应，由相应的二酮合成完全共轭的，形式上呈抗芳族的茚并[1,2- b ]芴（IF；参见结构）。它们的光电特性表明，茚并芴可以替代传统上并用的并五苯等并五苯，用于材料应用。

  DOI：

  10.1002/anie.201006312
• 作为产物：
  描述：

  1,2-Bis-decyl-4,5-diethynyl-benzene 以74%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：

文献信息

• Synthesis of Diacetylene Macrocycles Derived from 1,2-Diethynyl Benzene Derivatives: Structure and Reactivity of the Strained Cyclic Dimer
  作者：Qin Zhou、Patrick J. Carroll、Timothy M. Swager

  DOI：10.1021/jo00085a016

  日期：1994.3

  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.
• Spectroscopic properties of macrocyclic oligo(phenyldiacetylenes)-II. Synthesis and theoretical study of diacetylenic dehydrobenzoannulene derivatives with weak electron-donor and -acceptor groups
  作者：Boris Zimmermann、Goran Baranović、Zoran Štefanić、Marko Rožman

  DOI：10.1016/j.molstruc.2006.01.049

  日期：2006.8

  Diacetylenic dehydrobenzo[12]annulene and dehydrobenzo[18]annulene derivatives with electron-donor and -acceptor groups were synthesized (including push-pull Eglinton-Galbraith dimer derivative 1c) via an oxidative coupling reaction, and spectroscopically and structurally characterized. The solid-solid phase transition in 1b has been revealedat 45 degrees C by DSC measurements. Its room temperature crystal structure has been solved by X-ray diffraction measurements. The H-1 and C-13 NMR chemical shifts, UV/vis and infrared absorption spectra and Raman scattering spectra have been analyzed by using ground-state DFT calculations. The strongest absorptions in the UV/vis spectra of I and 2 most probably are not due to the HOMO -> LUMO excitations but due to the (HOMO-1)-> LUMO and HOMO ->(LUMO + 1) excitations. The substitution effects on the electronic charge distribution of the all-carbon annulenic cores can be particularly well observed in the distribution of IR intensities in the region of acetylenic stretching vibrations. IR intensities are thus useful in studying the extent of resonance interactions also in acetylenic macrocycles. (c) 2006 Elsevier B.V. All rights reserved.