1,8-di-(1-naphthyl)octa-1,3,5,7-tetrayne | 20199-32-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1,8-di-(1-naphthyl)octa-1,3,5,7-tetrayne
• 英文别名: Bis--octatetrain-(1.3.5.7)；1,1'-Dinaphthyltetraacetylen；1-(8-Naphthalen-1-ylocta-1,3,5,7-tetraynyl)naphthalene；1-(8-naphthalen-1-ylocta-1,3,5,7-tetraynyl)naphthalene
• CAS: 20199-32-0
• 化学式: C₂₈H₁₄
• 分子量: 350.419
• InChiKey: DWFDQYDNZPLMBF-UHFFFAOYSA-N

物化性质

• 沸点：
  567.9±33.0 °C(predicted)
• 密度：
  1.24±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  1-(1-Naphthyl)-2-butin-1,4-diol 在 吡啶 、 copper diacetate 作用下， 生成 1,8-di-(1-naphthyl)octa-1,3,5,7-tetrayne
  参考文献：
  名称：

  Linear Conjugated Systems Bearing Aromatic Terminal Groups. III. The Synthesis and the Electronic Spectra of 1,1′-Dinaphthyl- and 2,2′-Dinaphthylpoly-ynes

  摘要：

  合成了1,1′-二萘基多炔（In，n=1–6）和2,2′-二萘基多炔（IIn，n=1–6），并测量了它们的电子光谱。In系列的λmax与n1.5的关系非常吻合，而IIn系列则遵循直线关系，即λmax与n1.3成正比。这些关系与1,1′-二蒽基和9,9′-二蒽基多炔的情况不同，后者λmax与n^2的关系图呈现出非常好的直线（Bull. Chem. Soc. Jap., 39, 2320 (1966); 40, 340 (1967)）。在二萘基系列中发现的新线性关系进一步证明了端基对共轭多炔体系电子光谱特性的显著影响。

  DOI：

  10.1246/bcsj.43.3567

文献信息

• Synthesis, Characterization, and Modeling of Naphthyl-Terminated sp Carbon Chains: Dinaphthylpolyynes
  作者：Franco Cataldo、Luca Ravagnan、Eugenio Cinquanta、Ivano Eligio Castelli、Nicola Manini、Giovanni Onida、Paolo Milani

  DOI：10.1021/jp104863v

  日期：2010.11.25

  theoretical modeling of a series of α,ω-dinaphthylpolyynes. We synthesized this family of naphthyl-terminated sp carbon chains by reacting diiodoacetylene and 1-ethynylnaphthalene under the Cadiot−Chodkiewicz reaction conditions. By means of liquid chromatography (HPLC), we separated the products and recorded their electronic absorption spectra, which enabled us to identify the complete series of dinaphthylpolyynes

  我们报告了一系列α，ω-二萘基聚炔的合成，光谱表征和理论模型的组合研究。我们通过在Cadiot-Chodkiewicz反应条件下使二碘乙炔与1-乙炔基萘反应，合成了该萘基末端的sp碳链族。通过液相色谱（HPLC），我们分离了产物并记录了它们的电子吸收光谱，这使我们能够鉴定出完整的二萘基聚炔Ar-C 2 n -Ar系列（其中Ar =萘基，n =乙炔单元数） ），n的范围为2到6。在二萘基聚炔红色电子光谱中，最长的波长跃迁（LWT）随n线性移动远离裸终端的LWT。DFT-LDA仿真也支持此结果。最后，我们通过傅立叶变换红外光谱法和差示扫描量热法（DSC）探索了固态沉淀物中二萘基聚炔的稳定性。
• Synthesis of Diynes and Tetraynes from in Situ Desilylation/Dimerization of Acetylenes
  作者：Matthew A. Heuft、Shawn K. Collins、Glenn P. A. Yap、Alex G. Fallis

  DOI：10.1021/ol016414u

  日期：2001.9.1

  [GRAPHICS]An efficient method for the in situ desillylation/oxidative dimerization of (trialkylsilyl)acetylenes is described. This protocol avoids the complications encountered with sensitive diynes by eliminating the deprotection and isolation steps. Various aromatic and alkyl diynes and tetraynes can be synthesized in a straightforward manner in good yields (82-99%) from TIPS-protected acetylenes. This method facilitates the efficient synthesis of novel tetrayne-bridged acetylenic cyclophanes 6 and 7 in a direct manner.
• Linear Conjugated Systems Bearing Aromatic Terminal Groups. III. The Synthesis and the Electronic Spectra of 1,1′-Dinaphthyl- and 2,2′-Dinaphthylpoly-ynes
  作者：Kazuhiro Nakasuji、Shuzo Akiyama、Kazuko Akashi、Masazumi Nakagawa

  DOI：10.1246/bcsj.43.3567

  日期：1970.11

  1,1′-Dinaphthylpoly-ynes (In, n=1–6) and 2,2′-dinaphthylpoly-ynes (IIn, n=1–6) were synthesized, and their electronic spectra were measured. The In-series gave an excellent agreement with the λmax∝n1.5 relationship, and the IIn-series followed a straight line, λmax∝n1.3. These relationships are different from those of 1,1′-dianthryl- and 9,9′-dianthrylpory-ynes, in which the plots of λmax  versus  n2 give excellent straight lines (Bull. Chem. Soc. Jap., 39, 2320 (1966); 40, 340 (1967)). The new linear relationships found in the dinaphthyl-series offer further evidence of the prominent effect of the terminal groups upon the electronic spectral properties of the conjugated poly-yne system.

  合成了1,1′-二萘基多炔（In，n=1–6）和2,2′-二萘基多炔（IIn，n=1–6），并测量了它们的电子光谱。In系列的λmax与n1.5的关系非常吻合，而IIn系列则遵循直线关系，即λmax与n1.3成正比。这些关系与1,1′-二蒽基和9,9′-二蒽基多炔的情况不同，后者λmax与n^2的关系图呈现出非常好的直线（Bull. Chem. Soc. Jap., 39, 2320 (1966); 40, 340 (1967)）。在二萘基系列中发现的新线性关系进一步证明了端基对共轭多炔体系电子光谱特性的显著影响。