pyracylene | 187-78-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: pyracylene
• 英文别名: Pyracylen；Pyracyclen；Cyclopent[fg]acenaphthylene；tetracyclo[5.5.2.04,13.010,14]tetradeca-1(13),2,4,6,8,10(14),11-heptaene
• CAS: 187-78-0
• 化学式: C₁₄H₈
• 分子量: 176.218
• InChiKey: SFPDOMBOFWSXDM-UHFFFAOYSA-N

物化性质

• 沸点：
  659.2±22.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  0
• 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

• 作为反应物：
  描述：

  pyracylene 生成 乙炔 、 alkaline earth salt of/the/ methylsulfuric acid
  参考文献：
  名称：

  碳氢化合物的高温稳定性

  摘要：

  DOI：

  10.1021/j100263a027
• 作为产物：
  描述：

  5-乙酰-1,2-二氢苊烯 在 五氯化磷 作用下， 以 二氯甲烷 为溶剂， 1000.0 ℃ 、1.33 Pa 条件下， 反应 5.0h， 生成 pyracylene
  参考文献：
  名称：

  Sarobe, Martin; Flink, Simon; Jenneskens, Leonardus W., Journal of the Chemical Society. Perkin transactions II, 1996, # 10, p. 2125 - 2132

  摘要：

  DOI：

文献信息

• Trapping Aryl Radicals with Acetylene:  Evidence for C₂-Accretion as a Mechanism for Polycyclic Aromatic Hydrocarbon Growth¹
  作者：Atena Necula、Lawrence T. Scott

  DOI：10.1021/ja992115c

  日期：2000.2.1

  The formation of polycyclic aromatic hydrocarbons (PAH), fullerenes, soot, and other carbonaceous materials during the combustion or pyrolysis of low-molecular weight hydrocarbons requires, at a minimum, that small molecules and/or reactive intermediates somehow become joined to make larger ones. Most likely, more than one type of intermolecular C-C bond-forming reaction plays a role. The accretion

  在低分子量烃的燃烧或热解过程中，多环芳烃 (PAH)、富勒烯、烟灰和其他含碳材料的形成至少需要小分子和/或反应性中间体以某种方式结合起来形成更大的分子. 最有可能的是，不止一种类型的分子间 CC 键形成反应在起作用。长期以来，Csub 2} 单元的增加一直被认为是火焰中 PAH 逐步增长的可能途径，但证据也表明双分子过程的运作，其中双方都可以相对较大。
• Origin of Pyrene under High Temperature Conditions in the Gas Phase. The Pivotal Role of Phenanthrene
  作者：Martin Sarobe、Leonardus W. Jenneskens、Ralph G. B. Steggink、Tom Visser

  DOI：10.1021/jo982030e

  日期：1999.5.1

  4-Ethynylphenanthrene (15), and the latent precursors for 2-ethynyl- (18) and 3-ethynylphenanthrene (19), viz., 2-(1-chloroethenyl)- (16) and 3-(1-chloroethenyl)phenanthrene (17), respectively, have been subjected to flash vacuum thermolysis (FVT). Whereas at 800 degrees C 15 is quantitatively converted into pyrene (1), 16 and 17 only give 18 and 19, respectively. Both 18 and 19 contain redundant ethynyl substituents, i.e., after ethynyl-ethylidene carbene equilibration neither five- nor six-membered ring formation can occur by carbene C-H insertion. At T greater than or equal to 1000 degrees C 16 and 17 gave pyrolysates containing the same set of 11 (non)-alternant polycyclic aromatic hydrocarbons (PAH), albeit in a different ratio. The different product ratio suggests that redundant ethynyl substituents migrate along the phenanthrene periphery presumably via transient cyclobuta-PAH intermediates toward positions suitable for either five- or six-membered ring formation by carbene C-H insertion. The results provide an explanation for the ubiquitous formation of pyrene (1), acephenanthrylene (9), and fluoranthene (3) during (incomplete) combustion. Phenanthrene (2) appears to be a point of divergence in PAH growth by C-2 addition.
• Dehmlow, Eckehard V.; Fruend, Michael, Zeitschrift fur Naturforschung, B: Chemical Sciences, 1992, vol. 47, # 11, p. 1647 - 1648
  作者：Dehmlow, Eckehard V.、Fruend, Michael

  DOI：——

  日期：——
• Short time pyrolysis and spectroscopy of unstable compounds. Part 10. A simple synthesis of pyracyclene
  作者：Gerhard Schaden

  DOI：10.1021/jo00174a054

  日期：1983.12
• Molecular and electronic structure of pyracylene
  作者：Beat Freiermuth、Stefan Gerber、Andreas Riesen、Jakob Wirz、Margareta Zehnder

  DOI：10.1021/ja00158a037

  日期：1990.1

表征谱图