环戊二烯并(hi)醋菲烯 | 114959-37-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 中文名称: 环戊二烯并(hi)醋菲烯
• 英文名称: Cyclopent[h,i]acephananthrylene
• 英文别名: cyclopent[hi]acephenanthrylene；cyclopent[hi]acephenantrylene；Cyclopent(hi)acephenanthrylene；pentacyclo[8.6.1.12,5.014,17.09,18]octadeca-1,3,5(18),6,8,10,12,14(17),15-nonaene
• CAS: 114959-37-4
• 化学式: C₁₈H₁₀
• 分子量: 226.277
• InChiKey: OGSMXDUSWZTIEB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  5.0
• 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：

  9,10-苯并菲 1000.0 ℃ 、6.67 Pa 条件下， 生成 环戊二烯并(hi)醋菲烯
  参考文献：
  名称：

  Preparative flash vacuum thermolysis. Conversion of triphenylene to cyclopent[h,i]acephenanthrylene. A significant reaction for environmental science and combustion research

  摘要：

  环戊并[h,i]荧蒽在 1000 °C的闪蒸真空热解过程中选择性地形成了三亚苯；该反应代表了一种新的燃烧机理途径，产生了一种环戊并芳香族化合物。

  DOI：

  10.1039/cc9960000149

文献信息

• Formation of Cyclopent[hi]acephenanthrylene From 1,2-, 1,3-, 1,4- and 2,3-Triphenylenedicarboxylic Acid Derivatives on Flash Vacuum Pyrolysis at >900°C
  作者：MD Banciu、RFC Brown、KJ Coulston、FW Eastwood、C Jurss、I Mavropoulos、M Stanescu、UE Wiersum

  DOI：10.1071/ch9960965

  日期：——

  The processes involved in the conversion of triphenylene , C18H12, into cyclopent [hi] acephenanthrylene, C18H10, under flash vacuum pyrolytic conditions at 900-1100°C have been investigated by pyrolysing triphenylene-1,2- and -2,3-dicarboxylic anhydrides and diallyl triphenylene-1,3- and -1,4-dicarboxylates to give the corresponding didehydrotriphenylenes in the gas phase. These didehydro intermediates are converted into mixtures of cyclopent [hi] acephenanthrylene and triphenylene in different yields and proportions. Pyrolysis of 9,10-diethynylphenanthrene. C18H10, yields cyclopent [hi] acephenanthrylene in good yield. Pyrolysis of 1-nitrotriphenylene and allyl triphenylene-2-carboxylate to give the triphenylen-1-yl and -2-yl radicals leads to formation of the same products. Mechanisms involving radical rearrangements (C18H11 species) and benzyne-cyclopentadienylidenecarbene and ethyne-ethenylidene rearrangements (C18H10 species) are discussed.

  通过热解三亚苯基-1,2-和-2,3-二羧酸酐以及二烯丙基三亚苯基-1,3-和-1,4-二羧酸盐，研究了在 900-1100°C 的闪速真空热解条件下，三亚苯基（C18H12）转化为环戊［喜］杂蒽（C18H10）的过程。这些双脱氢中间体以不同的产率和比例转化为环戊二烯和三亚苯的混合物。热解 9,10-二乙炔基菲。C18H10，可得到环戊[hi]氧杂菲。热解 1-硝基三亚苯和三亚苯-2-羧酸烯丙基酯，得到三亚苯-1-基和-2-基自由基，形成相同的产物。讨论了涉及自由基重排（C18H11 物种）和苄-环戊二烯-亚乙基重排（C18H10 物种）的机理。
• Thermal migration of an ethynyl group from one benzene ring to another by reversible vinylidene CH insertion
  作者：Lawrence T. Scott、Atena Necula

  DOI：10.1016/s0040-4039(97)00225-6

  日期：1997.3

  Evidence is presented for the high temperature opening of a 5-membered ring by extrusion of a carbene (the reverse of a CH bond insertion), which results in the net thermal migration of an ethynyl group from one benzene ring to another.

  通过卡宾的挤出（C theH键插入的相反方向）显示了5元环高温打开的证据，这导致乙炔基从一个苯环到另一个苯环的净热迁移。
• Flash Vacuum Pyrolysis of [2,3-13C2]Triphenylene-2,3-dicarboxylic Anhydride: Formation of Labelled Cyclopent[hi]acephenanthrylene and Triphenylene
  作者：Roger F. C. Brown,、Karen J. Coulston、Frank W. Eastwood

  DOI：10.1071/c97120

  日期：——

  Flash vacuum pyrolysis (f.v.p.) of [2,3-13C2]triphenylene-2,3-dicarboxylic anhydride (c. 22·5% 13C2) at 950°C gave a pyrolysate which was analysed by 13C n.m.r. spectroscopy. The principal product was [2,3-13C2]triphenylene. The second major product was a 1 : 2 : 1 mixture of [4,7- 13C2]-, [4,6-13C2]- and [5,6-13C2]-cyclopent[hi]acephenanthrylene.

  闪速真空热解（f.v.p.） [2,3-13C2]triphenylene-2,3-dicarboxylic 酐（约 22-5 13C2）在 950°C 的温度下进行热分解（f. 通过 13C n.m.r. 光谱进行分析。主要产物是 [2,3-13C2]triphenylene. 第二种主要产物是 1 : 2 : 1 的 [4,7- 13C2]-, [4,6-13C2]- 和 [5,6-13C2]-环戊并[hi]荧蒽的 1 : 2 : 1 混合物。
• Synthesis of dicyclopenta-fused derivatives of phenanthrene
  作者：Patrick P. J. Mulder、Ben B. Boere、Jan Cornelisse、Johan Lugtenburg

  DOI：10.1002/recl.19931120403

  日期：——

  The synthesis of cyclopent[hi]acephenanthrylene (CPAP), a dicyclopenta-fused derivative of phenanthrene, is described. The 4,5-dihydro and 4,5,6,7-tetrahydro derivatives of CPAP were also prepared. These novel compounds are characterized by means of 1H-NMR, UV-VIS and mass spectrometry.

  环戊的合成[喜]醋菲烯（CPAP），菲的二环戊二烯并-稠合衍生物，进行说明。还制备了CPAP的4，5-二氢和4，5，6，7-四氢衍生物。这些新型化合物的特征在于1 H-NMR，UV-VIS和质谱。
• Flash vacuum thermolysis of 1,5-Bis-(1-chloroethenyl)anthracene. The thermal conversion of cyclopent[hi]aceanthrylene into cyclopent[hi]acephenanthrylene
  作者：Martin Sarobe、Judith D. Snoeijer、Leonardus W. Jenneskens、Jan W. Zwikker、Jolanda Wesseling

  DOI：10.1016/0040-4039(95)02049-7

  日期：1995.12

  Thermolysis of 1,5-bis-(1-chloroethenyl)anthracene (6) gives cyclopent[hi]-aceanthrylene (2) which at T≥9000 °C rearranges to cyclopent[hi]acephenanthrylene (1). This conversion occurs more readily than that of the monocyclopenta-fused aceanthrylene to acephenanthrylene.

  1，5-双-（1-氯乙烯基）蒽（6）的闪蒸真空热解得到环戊基[ hi ]-乙炔（2），其在T≥9000℃下重排成环戊基[ hi ]对菲（1）。这种转化比单环戊基稠合的乙炔向对苯二甲苯的转化更容易发生。