4,4'-di-n-pentyloxydiphenyldiacetylene | 501931-25-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4,4'-di-n-pentyloxydiphenyldiacetylene
• 英文别名: 1,4-bis[4-(n-pentyloxy)phenyl]buta-1,3-diyne；1,4-bis(p-(n-pentyloxy)phenyl)buta-1,3-diyne；1,4-bis(4-pentyloxyphenyl)buta-1,3-diyne；1,1'-(Buta-1,3-diyne-1,4-diyl)bis[4-(pentyloxy)benzene]；1-pentoxy-4-[4-(4-pentoxyphenyl)buta-1,3-diynyl]benzene
• CAS: 501931-25-5
• 化学式: C₂₆H₃₀O₂
• 分子量: 374.523
• InChiKey: GZBUHKOMITUDFC-UHFFFAOYSA-N

物化性质

• 沸点：
  506.1±50.0 °C(Predicted)
• 密度：
  1.05±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  28
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4,4'-di-n-pentyloxydiphenyldiacetylene 在 5%-palladium/activated carbon 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 12.0h， 以0.172 g的产率得到1,4-bis[4(n-pentyloxy)phenyl]butane
  参考文献：
  名称：

  Synthesis of Some Novel Aromatic Alkynyl Silanes: Mesomorphic Characterization of Ethynyl-Substituted Rod-Shaped Molecules

  摘要：

  The synthesis and characterization of 10 new rod-shaped substituted benzoates possessing the 4-(2-trimethylsilyl)ethynyl group in terminal phenyl position is reported employing the simple and efficient Sonogashira cross-coupling and DCC esterification. 4-Dodecylbiphenyl-4-carboxylic(2-trimethylsilylethynyl)-phenyl ester (3i), 4-(4-hexadecyloxybenzyloxy) carboxylic-4-trimethylsilanylethynyl-phenyl ester (3j), and 1,4-bis(4-(pentyloxy)phenyl)buta-1,3-diyne (7) compounds were evaluated for liquid crystal property. [Supplemental materials are available for this article. Go to the publisher's online edition of Molecular Crystals and Liquid Crystals to view the free supplemental file.]

  DOI：

  10.1080/15421406.2013.822299
• 作为产物：
  描述：

  4-乙炔基苯戊醚 在 四甲基乙二胺 、 氧气 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 copper(l) chloride 作用下， 以 乙腈 为溶剂， 以57%的产率得到4,4'-di-n-pentyloxydiphenyldiacetylene
  参考文献：
  名称：

  Synthesis of diphenyl-diacetylene-based nematic liquid crystals and their high birefringence properties

  摘要：

  我们合成了两系列基于二苯二炔（DPDA）的材料，分别为具有不同长度的烷氧基和烷基尾（DPDA–OCm和DPDA–Cm），并测量它们在不同波长和温度下的向列相双折射率（Δn）。我们发现，随着m的增加，Δn呈下降趋势，这可能是由于低Δn烷基尾的稀释效应。此外，在两组材料中，DPDA–OCm材料的Δn相对较高，在接近各向同性到向列相转变温度的10°C时，DPDA–OC1在550 nm处的Δn达到了最高值0.4。此外，我们观察到了Δn的温度依赖性，它与有序参数（s）成正比。从对s = 1（完美取向状态）的外推来看，可以推测DPDA–O基团具有提供非常大的Δn（0.9）的潜力。

  DOI：

  10.1039/c2jm16002a

文献信息

• An efficient approach to homocoupling of terminal alkynes: Solvent-free synthesis of 1,3-diynes using catalyticCu(ii) and base
  作者：Dong Wang、Jihui Li、Na Li、Tingting Gao、Sihua Hou、Baohua Chen

  DOI：10.1039/b917448f

  日期：——

  We report an environmentally friendly, efficient method for transforming terminal acetylenes into 1,3-diynes based on catalytic amounts of a Cu(II) salt and base under solvent-free conditions. The developed process conforms to the principles of ‘green’ chemistry and addresses the shortage of such methods for the synthesis of 1,3-diynes. The reaction is quite general and results in good yields. Interestingly

  我们报告了一种环保，高效的方法，可根据以下方法将末端乙炔转化为1,3-二炔 催化 金额 的Cu（II）盐和无溶剂条件下的碱。所开发的方法符合“绿色”化学原理，并解决了此类合成1,3-二炔的方法的不足。该反应是相当普遍的，并导致良好的产率。有趣的是，该系统还允许通过两个不同末端炔的交叉偶联来合成不对称的1,3-二炔。最后，催化剂 也可以回收。
• Leaf-like CuO nanosheets on rGO as an efficient heterogeneous catalyst for C-C homocoupling of terminal alkynes
  作者：Bin Wang、Lingfeng Gao、Gengxiu Zheng

  DOI：10.1016/j.catcom.2020.106260

  日期：2021.2

  CuO nanosheets/rGO were confirmed by XRD, SEM-EDS, TEM, HR-TEM, and XPS techniques. The CuO nanosheets/rGO was successfully applied as a high-performance heterogeneous catalyst in the homocoupling of 12 terminal alkynes, and the isolated yield of each product was more than 80%, except for propargyl alcohol. This catalyst could be reused five times with little activity loss. Thus, it is beneficial for

  在这项工作中，通过方便的水热法合成了在rGO上经济且定义明确的叶状CuO纳米片（CuO纳米片/ rGO）。通过XRD，SEM-EDS，TEM，HR-TEM和XPS技术确定了CuO纳米片/ rGO的形貌和化学组成。CuO纳米片/ rGO成功地用作高性能多相催化剂，用于12个末端炔的均相偶联，除炔丙醇外，每种产物的分离产率均超过80％。该催化剂可以重复使用五次而几乎没有活性损失。因此，对于有机合成化学的绿色和可持续发展是有益的。
• UV-Irradiated Formation of Diradicals of Diphenylbutadiyne and Some of Its<i>p,p</i>′-Disubstituted Derivatives
  作者：Miriam F. Beristain、Sergei Fomine、Eduardo Muñoz、Roberto Salcedo、Takeshi Ogawa

  DOI：10.1246/bcsj.78.1986

  日期：2005.11

  It was found for the first time that aromatic diacetylenes give strong ESR signals of stable carbon radical species in solution or in the solid state upon irradiation of UV light. The numbers of radicals reached to the order of 1020 radicals per mole of diacetylene, and the solution became red colored due to the formation of oligomers by their recombination. The radical species were stable almost indefinitely under an inert atmosphere. The unusual stability of these radicals is attributed to a resonance effect of aromatic rings linked to the butadiyne. Very slow quenching in the dark seems to be due to the recombination between them. Theoretical calculations indicated that monomeric diradicals on 1- and 4-carbons with the sp configuration, are formed, which combine to form dimeric or higher species detected by ESR spectroscopy.

  首次发现芳香二炔在紫外光照射下，在溶液或固态中生成稳定的碳自由基物种，产生强烈的电子自旋共振（ESR）信号。自由基的数量达到了每摩尔二炔约10^20个，自溶液由于其重组形成聚合物而变成红色。在惰性气氛下，这些自由基几乎无限稳定。这些自由基的不寻常稳定性归因于与丁二炔相连的芳香环的共振效应。在黑暗中非常缓慢的湮灭似乎是由于它们之间的重组。理论计算表明，在1-和4-碳上的单体双自由基以sp构型形成，这些自由基结合形成通过ESR光谱检测到的二聚体或更高物种。
• Ordering of apolar and polar solutes in nematic solvents
  作者：T. Dingemans、D. J. Photinos、E. T. Samulski、A. F. Terzis、C. Wutz

  DOI：10.1063/1.1560941

  日期：2003.4.15

  measured by nuclear magnetic resonance (NMR) in the nematic solvents hexyl- and pentyloxy-substituted diphenyl diacetylene (DPDA-C6 and DPDA-OC5, respectively). Measurements are taken for all four combinations of the nominally apolar (1,4-DCB) and polar (1,2-DCB) solutes in the apolar (DPDA-C6) and polar (DPDA-OC5) solvents, and throughout the entire nematic temperature range of the solutions. The temperature

  通过核磁共振 (NMR) 在向列溶剂己基和戊氧基取代的二苯基联乙炔 (DPDA- C6 和 DPDA-OC5，分别）。对非极性 (DPDA-C6) 和极性 (DPDA-OC5) 溶剂以及整个向列型溶剂中标称非极性 (1,4-DCB) 和极性 (1,2-DCB) 溶质的所有四种组合进行测量溶液的温度范围。从这些测量中获得了溶质的二级取向有序参数的温度依赖性，并且溶剂分子的介晶核的相应有序参数独立于碳 13 NMR 测量获得。发现两种溶质的顺序参数分布非常不同，但从一种溶剂到另一种溶剂几乎没有变化。使用 atomist 根据潜在的分子相互作用对结果进行分析和解释...
• Iron/copper promoted oxidative homo-coupling reaction of terminal alkynes using air as the oxidant
  作者：Xu Meng、Chuanbin Li、Baochun Han、Tiansheng Wang、Baohua Chen

  DOI：10.1016/j.tet.2010.04.017

  日期：2010.6

  An inexpensive catalytic system, which used a readily available Fe(acac)(3) and trace quantity of Cu (acac)(2) as the co-catalyst and air as the oxidant for the homo-coupling of terminal alkynes, has been developed. The catalytic system could also apply to the cross-coupling reaction of two different terminal alkynes. (C) 2010 Elsevier Ltd. All rights reserved.