benzene<3-1,3,5>:5-ethynyl-1,3-ditertbutylbenzene | 155064-29-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: benzene<3-1,3,5>:5-ethynyl-1,3-ditertbutylbenzene
• 英文别名: 1,3,5-Tris[(3,5-di-tert-butylphenyl)ethynyl]benzene；1,3,5-tris[2-(3,5-ditert-butylphenyl)ethynyl]benzene
• CAS: 155064-29-2
• 化学式: C₅₄H₆₆
• 分子量: 715.118
• InChiKey: VLNZYGOWUWOWBJ-UHFFFAOYSA-N

物化性质

• 沸点：
  742.7±60.0 °C(Predicted)
• 密度：
  1.02±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  18
• 重原子数：
  54
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  在 chloro(1,5-cyclooctadiene)rhodium(I) dimer 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 作用下， 以 乙基苯 为溶剂， 反应 24.0h， 以74%的产率得到benzene<3-1,3,5>:5-ethynyl-1,3-ditertbutylbenzene
  参考文献：
  名称：

  Rh 催化碳-炔键活化共轭炔酮脱羰：通过 DFT 计算进行反应范围和机理探索

  摘要：

  在这篇完整的文章中，详细描述了共轭单炔酮催化脱羰合成二取代炔烃的进展。反应范围和局限性已被彻底研究，并且......

  DOI：

  10.1039/c5sc00584a

文献信息

• Phenylacetylene Dendrimers by the Divergent, Convergent, and Double-Stage Convergent Methods
  作者：Zhifu Xu、Michael Kahr、Kathleen L. Walker、Charles L. Wilkins、Jeffrey S. Moore

  DOI：10.1021/ja00090a002

  日期：1994.6

  The divergent, convergent, and double-stage convergent methods for synthesizing phenylacetylene dendritic macromolecules are examined. Syntheses based on the divergent or double-stage convergent approaches are severely hampered by poor solubility of the growing macromolecules. The double-stage method is nonetheless successfully used in attaining a high molecular weight and apparently monodisperse dendrimer. Using the convergent approach, high molecular weight mono- and tridendrons are prepared. The repetitive chemistry employed for monodendron preparation includes palladium-catalyzed coupling of terminal acetylenes to an aromatic dibromide containing a trimethylsilyl (TMS) masked terminal acetylene. The synthetic cycle is completed by removing the TMS group under mildly basic conditions. These monodendrons can be coupled around a trifunctional core, such as triiodobenzene, yielding tridendrons. Solubility of both the mono- and the tridendrons is strongly dependent on the nature of the peripheral group. Qualitatively, solubility tends to plummet in the early stages of growth. Provided that growth can be sustained, however, this trend tends to reverse as the synthesis progresses. The best peripheral group of those examined thus far for maintaining adequate solubility of both mono- and tridendrons over this critical solubility minimum is di-tert-butylphenylacetylene. For dendrimers containing this peripheral group, solubility is high even in aliphatic hydrocarbon solvents at room temperature. When poor solubility does not hamper the synthesis, the limiting factors to sustaining growth become as much dependent on the ability to purify and characterize the product of the coupling reaction as on the chemistry of the coupling reaction itself. Size-exlusion chromatography is shown to be inadequate for differentiating partially coupled products from fully coupled tridendrons. This problem is believed to be especially severe for stiff dendritic macromolecules, since their molecular cross section is essentially constant once two of the three monodendrons have coupled to the central core. Unequivocal proof of structure for mono- and tridendrons through generation four (C1134H1146, mol wt 14 776) has been obtained using a combination of chromatographic techniques, isotope labeling studies, mass spectrometry, and multidimensional NMR experiments.
• Energy Transfer in Dendritic Macromolecules:  Molecular Size Effects and the Role of an Energy Gradient
  作者：Chelladurai Devadoss、P. Bharathi、Jeffrey S. Moore

  DOI：10.1021/ja961418t

  日期：1996.1.1

  Perylene-terminated monodendrons 1-7 and phenyl-terminated reference monodendrons 8-14 have been synthesized, and the intramolecular energy transfer has been studied using steady-state as well as time-resolved fluorescence spectroscopy. In the series 2-7, the light-harvesting ability of these compounds increases with increasing generation due to the increase in molar extinction coefficient. However, the efficiency of the energy transfer decreases with increasing generation in this series. With increasing generation, the photoluminescence intensity from the perylene core still increases and the expected level-off in the photoluminescence intensity has not been reached in this series of compounds. Dendrimer 1 is unique in that the energy transfer in this molecule occurs at a very fast rate. The rate constant for energy transfer in 1 is at least 2 orders of magnitude larger than in 2-7. In contrast to monodendrons 2-7, 1 possesses a variable monomer type at each generation that creates an energy funnel. The ultrafast energy transfer in this system is best explained by the presence of this energy gradient.
• Xu Zhifu, Kahr Michael, Walker Kathleen L., Wilkins Charles L., Moore Jef+, J. Amer. Chem. Soc, 116 (1994) N 11, S 4537-4550
  作者：Xu Zhifu, Kahr Michael, Walker Kathleen L., Wilkins Charles L., Moore Jef+

  DOI：——

  日期：——
• Xu, Zhifu; Moore, Jeffrey S., Angewandte Chemie, 1993, vol. 105, # 9, p. 1394 - 1396
  作者：Xu, Zhifu、Moore, Jeffrey S.

  DOI：——

  日期：——
• Rh-catalyzed decarbonylation of conjugated ynones via carbon–alkyne bond activation: reaction scope and mechanistic exploration via DFT calculations
  作者：Alpay Dermenci、Rachel E. Whittaker、Yang Gao、Faben A. Cruz、Zhi-Xiang Yu、Guangbin Dong

  DOI：10.1039/c5sc00584a

  日期：——

  In this full article, detailed development of a catalytic decarbonylation of conjugated monoynones to synthesize disubstituted alkynes is described. The reaction scope and limitation has been thoroughly investigated, and a...

  在这篇完整的文章中，详细描述了共轭单炔酮催化脱羰合成二取代炔烃的进展。反应范围和局限性已被彻底研究，并且......