3,4-bis(phenylethynyl)-3-cyclobutene-1,2-dione | 125358-17-0

• 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: 3,4-bis(phenylethynyl)-3-cyclobutene-1,2-dione
• 英文别名: 3,4-Bis(2-phenylethynyl)cyclobut-3-ene-1,2-dione
• CAS: 125358-17-0
• 化学式: C₂₀H₁₀O₂
• 分子量: 282.298
• InChiKey: RMFWEHGOUZKTOZ-UHFFFAOYSA-N

物化性质

• 沸点：
  409.7±55.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,4-bis(phenylethynyl)-3-cyclobutene-1,2-dione 以 苯 为溶剂， 以88%的产率得到1,6-diphenyl-1,3,5-hexatriyne
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1021/ja00018a035
• 作为产物：
  描述：

  2,3-Bis-phenylethynyl-buta-1,3-diene-1,4-dione 以 异辛烷 为溶剂， 生成 3,4-bis(phenylethynyl)-3-cyclobutene-1,2-dione
  参考文献：
  名称：

  通过闪光光解和闭环动力学从环丁烯-1,2-二酮生成 1,2-双烯酮1a

  摘要：

  环丁烯-1,2-二酮 (1) 和 1,2-双烯酮 (RCCO)2 (2) 的相互转化已针对不同的取代基组合 R = H、Me、t-Bu、Ph、Me3Si、CN、 Cl、Br、R1O、炔基和PhS。双烯酮 2 是通过闪光光解产生的，并且通过时间分辨红外和紫外光谱研究了它们转化为 1 的动力学。2 的闭环速率常数与乙烯酮稳定参数 (SE) 和计算的势垒相关。二叔丁基双烯酮 2g 至环丁烯二酮 1g 的闭环速率常数仅比二甲基类似物小 40 倍，显示出相当适中的空间位阻。quinoketene 2s 的闭环速度很快，但没有根据计算的几何和热力学因素预期的那么快。

  DOI：

  10.1021/ja9722685

文献信息

• Precursors to the cyclo[n]carbons: from 3,4-dialkynyl-3-cyclobutene-1,2-diones and 3,4-dialkynyl-3-cyclobutene-1,2-diols to cyclobutenodehydroannulenes and higher oxides of carbon
  作者：Yves Rubin、Carolyn B. Knobler、Francois Diederich

  DOI：10.1021/ja00160a047

  日期：1990.2

  downfield resonances of the terminal acetylenic carbon atoms in the sup 13}C NMR spectra of the 3,4-dialkynyl-3-cyclobutene-1,2-diones are discussed. The oxidative Hay coupling of the acetonide of 3,4-diethynyl-3-cyclobutene-1,2-diol or of the bis(ethylene ketal) of 3,4-diethynyl-3-cyclobutene-1,2-dione gave two series of cyclobutenodehydroannulenes with 18pi}-, 24pi}-, and 30pi}-electron perimeters

  一系列新型环丁烯脱氢 (n) 环烯 (n = 18, 24, 30) 已被制备为环碳 Csub 18}、Csub 24} 和 Csub 30} 的有机方法的前体。在通往这些大环的道路上，已经开发了三类新烯二炔的合成条目。双（1-丙炔基）环丙烯酮是在 1-（三甲基甲硅烷基）-1-丙炔与三氯环丙烯鎓四氯铝酸盐的反应中制备的。3,4-dialkynyl-3-cyclobutene-1,2-dionines 是通过 3,4-dichloro-3-cyclobutene-1,2-dione 与 (tri-n-butylstannyl) 炔烃在存在下反应制备的催化量的 Pd(PPhsub 3})sub 4} 或与（三烷基甲硅烷基）乙炔的可溶性铜 (I) 乙炔化物。3,4-二炔基-3-环丁烯-1的sup 13}C NMR谱中末端炔碳原子的特殊低场共振，讨论了 2-diones。3,4-二乙炔-3-环丁烯-1
• Generation of 1,2-Bisketenes from Cyclobutene-1,2-diones by Flash Photolysis and Ring Closure Kinetics¹^a
  作者：Annette D. Allen、Jim D. Colomvakos、François Diederich、Ian Egle、Xiaokuai Hao、Ronghua Liu、Janusz Lusztyk、Jihai Ma、Michael A. McAllister、Yves Rubin、Kuangsen Sung、Thomas T. Tidwell、Brian D. Wagner

  DOI：10.1021/ja9722685

  日期：1997.12.17

  The bisketenes 2 have been generated by flash photolysis, and the kinetics of their conversion to 1 have been studied by time-resolved infrared and ultraviolet spectroscopy. The rate constants of the ring closure of 2 are correlated by the ketene stabilization parameters (SE) and with calculated barriers. The rate constant of ring closure of the di-tert-butyl bisketene 2g to cyclobutenedione 1g is

  环丁烯-1,2-二酮 (1) 和 1,2-双烯酮 (RCCO)2 (2) 的相互转化已针对不同的取代基组合 R = H、Me、t-Bu、Ph、Me3Si、CN、 Cl、Br、R1O、炔基和PhS。双烯酮 2 是通过闪光光解产生的，并且通过时间分辨红外和紫外光谱研究了它们转化为 1 的动力学。2 的闭环速率常数与乙烯酮稳定参数 (SE) 和计算的势垒相关。二叔丁基双烯酮 2g 至环丁烯二酮 1g 的闭环速率常数仅比二甲基类似物小 40 倍，显示出相当适中的空间位阻。quinoketene 2s 的闭环速度很快，但没有根据计算的几何和热力学因素预期的那么快。
• 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.