1,12-bis(phenyl)-1,3,5,7,9,11-dodecahexayne | 20264-58-8

• 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: 1,12-bis(phenyl)-1,3,5,7,9,11-dodecahexayne
• 英文别名: 1,12-diphenyl-1,3,5,7,9,11-dodecahexayne；1,12-diphenyldodeca-1,3,5,7,9,11-hexayne；diphenyl-dodecahexayne；Diphenyl-dodecahexain；Bis--dodecahexain-(1.3.5.7.9.11)；Benzene, 1,1'-(1,3,5,7,9,11-dodecahexayne-1,12-diyl)bis-；12-phenyldodeca-1,3,5,7,9,11-hexaynylbenzene
• CAS: 20264-58-8
• 化学式: C₂₄H₁₀
• 分子量: 298.343
• InChiKey: MLWMBPSCAZWEPG-UHFFFAOYSA-N

物化性质

• 熔点：
  133 °C (decomp)
• 沸点：
  466.8±28.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• 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

• 作为反应物：
  描述：

  二氯甲烷 、 1,12-bis(phenyl)-1,3,5,7,9,11-dodecahexayne 、 perfluoro-o-phenylenemercury trimer 以 二氯甲烷 为溶剂， 以20%的产率得到
  参考文献：
  名称：

  与三齿路易斯酸[ o -C 6 F 4 Hg] 3络合的超分子稳定α，ω-二苯基聚炔。

  摘要：

  三聚体（全氟的相互作用Ô（[亚苯基）汞ö -C 6 ˚F 4汞柱] 3，1）与α，含有4，6，8，12和sp 3碳原子的ω-diphenylpolyynes在CH 2氯2引线形成（1）2 ·Ph（C⋮C）2 Ph（2），1 ·Ph（C⋮C）3 Ph（3），（1）2 ·Ph（C⋮C）4 Ph（4）和（1）2 ·Ph（C⋮C）6 Ph·CH2 Cl 2（5）。加合物2 - 4已经通过元素分析，X射线晶体学，红外光谱和荧光光谱，差示扫描量热法，和热重分析。在固态中，近似平面的α，ω-二苯基聚炔通过二次Hg-π相互作用与分子平面任一侧的1分子缔合。的炔属延伸2 - 5通过IR光谱测量的是与自由聚炔烃的基本上相同。虽然加合物3 - 5仅在紫外线照射下仅产生微弱的发射，发光光谱2表示荧光完全淬灭，并显示出重原子诱导的发射，其能量和电子振动的进展与纯二炔的磷光报道的相同。DSC / TGA研究表明，加合物2

  DOI：

  10.1021/om060186w
• 作为产物：
  描述：

  1-phenyl-5-(trimethylsilyl)penta-2,4-diyn-1-one 在 正丁基锂 、 四甲基乙二胺 、 氧气 、 potassium carbonate 、 三苯基膦 、 copper(l) chloride 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 various solvents 为溶剂， 反应 6.25h， 生成 1,12-bis(phenyl)-1,3,5,7,9,11-dodecahexayne
  参考文献：
  名称：

  Synthesis, Structure, and Nonlinear Optical Properties of Diarylpolyynes

  摘要：

  A series of alpha,omega-diarylpolyynes has been synthesized. In addition to the synthesis of three hexaynes (3a-c), a notably improved synthesis of 1,16-diphenylhexadecaoctayne (5) is described. The third-order nonlinear optical characteristics for these molecules have been studied and show a substantial increase in molecular hyperpolarizability (gamma) as a function of increasing length. The unusual solid-state structures of compounds 3a and 3b are reported.

  DOI：

  10.1021/ol047931q

文献信息

• Novel Approach to Stabilize Unstable Molecular Wires by Simultaneous Rotaxane Formation – Synthesis of Inclusion Complexes of Oligocarbynes with Cyclic Host Molecules
  作者：Jiro Sugiyama、Ikuyoshi Tomita

  DOI：10.1002/ejoc.200700630

  日期：2007.10

  An effective method to stabilize oligocarbynes as a modelfor polycarbyne by the simultaneous complexation withα-cyclodextrin (α-CD) is described. 1,12-Bis(9-phenanthryl)-1,3,5,7,9,11-dodecahexayne possessing one or two α-CD molecules was prepared by the oxidative coupling reaction of the corresponding triyne in the presence of α-CD. The resulting rotaxanes proved to be stable enough in comparison with

  描述了一种通过同时与 α-环糊精 (α-CD) 络合来稳定作为聚碳炔模型的低聚碳炔的有效方法。1,12-双(9-菲基)-1,3,5,7,9,11-十二己炔在α-CD存在下通过相应的三炔的氧化偶联反应制备了一个或两个α-CD分子. 与相应的游离低聚炔相比，所得轮烷证明足够稳定。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)
• An Iterative Method for the Synthesis of Symmetric Polyynes
  作者：Racquel C. DeCicco、Allison Black、Lei Li、Nancy S. Goroff

  DOI：10.1002/ejoc.201200442

  日期：2012.9

  An iterative synthetic route for obtaining symmetric polyynes was developed, consisting of a series of iodination and Stille coupling reactions. The starting materials employed in this pathway are simple and can be prepared easily. Polyynes containing up to seven C≡C bonds were synthesized using this method. This route is particularly effective for accessing polyynes with an odd number of C≡C bonds

  开发了获得对称聚炔的迭代合成路线，包括一系列碘化和斯蒂勒偶联反应。该途径中使用的起始材料简单且易于制备。使用这种方法合成了含有多达七个 C≡C 键的聚炔。该路线对于获得具有奇数个 C≡C 键的聚炔特别有效，并允许合成新的碘封端聚炔，二碘十碳五炔。
• β-Chlorovinylsilanes as masked alkynes in oligoyne assembly: synthesis of the first aryl-end-capped dodecayne
  作者：Simon M. E. Simpkins、Michael D. Weller、Liam R. Cox

  DOI：10.1039/b707681a

  日期：——

  An aryl-end-capped dodecayne has been prepared using a four-fold fluoride-mediated dechlorosilylation of a masked dodecayne precursor containing four β-chlorovinylsilane residues that serve as masked alkynes; the unstable dodecayne product has been characterised by UV-vis absorption spectroscopy and ‘matrix-free’ MALDI-TOF mass spectrometry.

  利用氟化物介导的四倍脱氯硅烷化作用，制备了一种芳基末端封端的十二烷，该封端十二烷前体含有四个作为封端炔烃的δ-氯乙烯基硅烷残基；不稳定的十二烷产物通过紫外-可见吸收光谱和 "无基质 "MALDI-TOF质谱进行了表征。
• Armitage et al., Journal of the Chemical Society, 1954, p. 147,153
  作者：Armitage et al.

  DOI：——

  日期：——
• β-Halovinylsilanes in oligoyne synthesis: a fluoride-catalysed unmasking of alkynes from β-fluorovinylsilanes
  作者：Michael D. Weller、Benson M. Kariuki、Liam R. Cox

  DOI：10.1016/j.tetlet.2008.05.081

  日期：2008.7

  A stereoselective haloclestannylation of (E)-beta-stannylvinyisilane 6 has been used to access a range of (E)-beta-halovinylsilanes. Most notably, the beta-fluorovinylsilane 14 was accessed in high yield using the Select-fluor (R) reagent, and subsequently converted into a masked hexayne 22. Release of the hexayne 25 was achieved by exposing 22 to sub-stoichiometric quantities of fluoride. (c) 2008 Elsevier Ltd. All rights reserved.