1,10-diphenyl-1,3,5,7,9-decapentayne | 20264-57-7

• 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: 1,10-diphenyl-1,3,5,7,9-decapentayne
• 英文别名: Bis--decapentain-(1.3.5.7.9)；α,ω-Diphenyl-decapentain；1,10-bis(phenyl)-1,3,5,7,9-decapentayne；diphenyl-decapentayne；Diphenyl-decapentain；10-Phenyldeca-1,3,5,7,9-pentaynylbenzene
• CAS: 20264-57-7
• 化学式: C₂₂H₁₀
• 分子量: 274.321
• InChiKey: XNOTWBBQMKEBBF-UHFFFAOYSA-N

物化性质

• 熔点：
  167-168 °C
• 沸点：
  435.9±28.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  22
• 可旋转键数：
  6
• 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

• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 乙醚 、 氨 、 sodium amide 作用下， 生成 1,10-diphenyl-1,3,5,7,9-decapentayne
  参考文献：
  名称：

  Nakagawa et al., Nippon Kagaku Zasshi, 1952, vol. 73, p. 141,145

  摘要：

  DOI：

文献信息

• 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。
• Synthesis and 13C NMR Spectroscopy of 13C-Labeled α,ω-Diphenylpolyynes
  作者：Rik Tykwinski、Thanh Luu

  DOI：10.1055/s-0031-1290983

  日期：2012.6

  The synthesis of three C-13-labeled alpha,omega-diphenylpolyynes is described. The known positions of the labeled carbon atoms allow assignment of the resonances in the C-13 NMR spectra and identification of trends in the chemical shifts.
• Solution-spray flash vacuum pyrolysis: a new method for the synthesis of linear poliynes with odd numbers of C.tplbond.C bonds from substituted 3,4-dialkynyl-3-cyclobutene-1,2-diones
  作者：Yves Rubin、Sophia S. Lin、Carolyn B. Knobler、John Anthony、Armen M. Boldi、Francois Diederich

  DOI：10.1021/ja00018a035

  日期：1991.8

  We report a new method for the preparation of a wide range of linear poliynes, 1a-1i, with an odd number of C = C bonds. This method is based on solution-spray flash vacuum pyrolysis (SS-FVP) of the readily available 3,4-dialkynyl-3-cyclobutene-1,2-diones 3a-3i. It allows the synthesis of multigram quantities of a series of hexatriynes and decapentaynes from poorly volatile and thermally unstable precursors that cannot be subjected to conventional flash vacuum pyrolysis. Yields of the linear poliynes range from 42 to 99%. Similarly, the dodecahexayne 1j was obtained in 31% yield by SS-FVP of the bis(3-cyclobutene-1,2-dione) 3j. The synthesis of the new 3,4-dialkynyl-3-cyclobutene-1,2-diones 3h-3j via the ketals 7, 10, and 13 is reported. The X-ray crystal structure of 1,10-diphenyl-1,3,5,7,9-decapentayne (1c) was solved, and the crystal packing structure provides valuable information to explain the thermal polymerization behavior observed for this compound in the crystalline state.