phenanthrene-4,5-dicarbaldehyde | 16162-34-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: phenanthrene-4,5-dicarbaldehyde
• CAS: 16162-34-8
• 化学式: C₁₆H₁₀O₂
• 分子量: 234.254
• InChiKey: UPGCIXBMSHYILQ-UHFFFAOYSA-N

物化性质

• 熔点：
  166-169 °C(Solv: ethyl acetate (141-78-6))
• 沸点：
  471.2±18.0 °C(Predicted)
• 密度：
  1.294±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  18
• 可旋转键数：
  2
• 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：

  phenanthrene-4,5-dicarbaldehyde 在 Β-苯乙烯甲醚 作用下， 以 乙醚 为溶剂， 以7%的产率得到pyrene monoozonide
  参考文献：
  名称：

  McCullough, Kevin J.; Sugimoto, Toshiya; Tanaka, Shogo, Journal of the Chemical Society. Perkin transactions I, 1994, # 6, p. 643 - 652

  摘要：

  DOI：
• 作为产物：
  描述：

  pyrene monoozonide 在 sodium iodide 作用下， 以 溶剂黄146 为溶剂， 反应 4.0h， 以25%的产率得到phenanthrene-4,5-dicarbaldehyde
  参考文献：
  名称：

  Approaches to the Azahelicene System: Synthesis and Spectroscopic Characterization of Some Diazapentahelicenes

  摘要：

  DOI：

  10.1002/1522-2675(200201)85:1<1::aid-hlca1>3.0.co;2-c

文献信息

• DEGRADATION OF POLYCYCLIC AROMATIC HYDROCARBONS TO RENDER THEM AVAILABLE FOR BIODEGRADATION
  申请人：Hong P.K. Andy

  公开号：US20080242875A1

  公开（公告）日：2008-10-02

  A method for the degradation of polycyclic aromatic compounds is disclosed that involves dissolving ozone in a bipolar solvent comprising a non-polar solvent in which is of sufficiently non-polar character to solubilized the polycyclic aromatic compounds, and a polar-water-compatible solvent which is fully miscible with the non-polar solvent to form a single phase with the non-polar solvent. The bipolar solvent with dissolved ozone is contacted with the polycyclic aromatic compounds to solubilize the polycyclic aromatic compounds and react the dissolved polycyclic aromatic compounds with the ozone to degrade the dissolved polycyclic aromatic compounds to oxygenated intermediates. The bipolar solvent is then mixed with sufficient water to form separate non-polar and polar phases, the non-polar phase comprising the non-polar solvent and the polar phase comprising the non-polar solvent and the oxygenated intermediates. The polar phase is then diluted and incubated with bacteria to biodegrade the oxygenated intermediates.

  揭示了一种降解多环芳烃化合物的方法，涉及将臭氧溶解在一种双极溶剂中，该溶剂包括一种非极性溶剂，其具有足够的非极性特性以溶解多环芳烃化合物，以及一种极性-水相容溶剂，与非极性溶剂完全互溶以形成与非极性溶剂相同的单一相。将含有溶解臭氧的双极溶剂与多环芳烃化合物接触，以溶解多环芳烃化合物并使溶解的多环芳烃化合物与臭氧反应，将溶解的多环芳烃化合物降解为含氧中间体。然后将双极溶剂与足够的水混合以形成分离的非极性和极性相，其中非极性相包括非极性溶剂，极性相包括非极性溶剂和含氧中间体。然后将极性相稀释并与细菌孵育以生物降解含氧中间体。
• Syntheses, structure analyses, and reactions of 1,3,5-trioxepanes and related compounds
  作者：Kevin J. McCullough、Araki Masuyama、Keith M. Morgan、Masatomo Nojima、Yuji Okada、Syuzo Satake、Shin-ya Takeda

  DOI：10.1039/a802928h

  日期：——

  Acid-catalysed condensations of 1,5- or 1,6-dicarbonyl compounds with ethylene glycol give 1,3,5-trioxepane derivatives as a result of neighbouring participation by the adjacent carbonyl group during the acetalization process. With trimethylene glycol, the related 1,3,5-trioxocanes have also been obtained. Reaction of the 1,3,5-trioxepanes with (a) Grignard reagents gives dialkyl-substituted cyclic

  1，5-或1，6-二羰基化合物与乙二醇的酸催化缩合产生1,3,5-三氧杂环丁烷衍生物，这是由于缩醛化过程中相邻羰基的相邻参与。使用三亚甲基二醇，也已经获得了相关的1,3,5-三氧杂环丁烷。1,3,5-三氧杂环丁烷与（a）格氏试剂反应生成二烷基取代的环状醚，（b）四氯化钛-烯丙基三丁基锡生成二烯丙基取代的环状醚，（c）在三氟甲磺酸三甲基甲硅烷基酯存在下的三乙基硅烷提供了相应的环醚。
• Mechanistic Insights into Selective Oxidation of Polyaromatic Compounds using RICO Chemistry
  作者：Ewa Nowicka、Niamh W. Hickey、Meenakshisundaram Sankar、Robert L. Jenkins、David W. Knight、David J. Willock、Graham J. Hutchings、Manuel Francisco、Stuart H. Taylor

  DOI：10.1002/chem.201800423

  日期：2018.8.22

  phenanthrene and pyrene substrates. These diketone products are shown to be stable under our reaction conditions so that higher oxidation products (acids and their derivatives) are assigned to the competing pathway through the dialdehyde. Experiments using 18O‐labelled water do show incorporation of oxygen from the solvents into products, but this may take place during the formation of the reactive RuO4

  聚芳烃（PAHs）的钌离子催化氧化（RICO）已通过实验和计算方法进行了详细研究，以探索反应机理。DFT计算表明，在这些反应中的区域选择性可以通过在最孤立的双键处最初形成[3 + 2]金属环中间体的芳族保留来理解。我们确定了两种竞争途径：导致双醛的C–C键断裂和C–H活化，然后H迁移至RuO x复合产生二酮。实验上，of和菲的氧化已在单相和双相溶剂系统中进行。我们的结果表明，二酮是菲和pyr底物的主要产物。这些二酮产物在我们的反应条件下被证明是稳定的，因此较高的氧化产物（酸及其衍生物）被分配给通过二醛的竞争途径。使用18 O标记水的实验确实显示出溶剂中的氧气会混入产品中，但这可能发生在反应性RuO 4物种形成过程中，而不是直接在PAH氧化过程中发生。使用D 2进行pyr的氧化时O，观察到动力学同位素效应（KIE），这意味着水参与了生成二酮产物的速率确定步骤。
• Oxidation of Polynuclear Aromatic Hydrocarbons using Ruthenium-Ion-Catalyzed Oxidation: The Role of Aromatic Ring Number in Reaction Kinetics and Product Distribution
  作者：Ewa Nowicka、Tomos J. Clarke、Meenakshisundaram Sankar、Robert L. Jenkins、David W. Knight、Stanislaw Golunski、Graham J. Hutchings、David J. Willock、Manuel Francisco、Stuart H. Taylor

  DOI：10.1002/chem.201704133

  日期：2018.1.12

  aromatic rings. Competitive oxidation between substrates with different numbers of aromatic rings has been studied in detail. It was found that the rate of polyaromatic hydrocarbon oxidation increases with the number of fused aromatic rings. A similar trend was also identified for alkylated aromatic hydrocarbons. The proof‐of‐concept investigation provides new insight into selective oxidation chemistry

  使用钌离子催化氧化（RICO）在两种溶剂环境（单相和双相）中研究了具有不同稠合芳环数（2-5）的芳烃的氧化。RICO通过选择性氧化开环以受控方式降低了分子中多芳烃核的芳香性。此外，对于具有两个以上芳环的分子，溶剂系统的性质决定了产物的类型和分布。已经详细研究了具有不同数量的芳环的底物之间的竞争性氧化。发现聚芳烃的氧化速率随稠合芳环数目的增加而增加。对于烷基化的芳烃也发现了类似的趋势。
• Rediscovering Bacon's hydrazine/phenylhydrazine mediated cyclization of 2,2′-dicarbonylbi(hetero)aryls: construction of (5-azo)-/indazolo[2,3-<i>a</i>]quinolines
  作者：Pawan S. Dhote、Chepuri V. Ramana

  DOI：10.1039/d1ob02207e

  日期：——

  Hydrazine/phenylhydrazine-mediated reductive dicarbonyl coupling reactions have been carried out under mild conditions to provide polycyclic aromatic compounds and azo-substituted polyaromatic compounds. This method has a broad substrate scope with good functional group compatibility.

  肼/苯肼介导的还原性二羰基偶联反应在温和条件下进行，以提供多环芳族化合物和偶氮取代的多芳族化合物。该方法底物适用范围广，官能团相容性好。