3,4-bis(4-fluorophenyl)-2,5-diphenylcyclopenta-2,4-dienone | 56805-29-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 3,4-bis(4-fluorophenyl)-2,5-diphenylcyclopenta-2,4-dienone
• 英文别名: 3,4-Bis-(p-fluor-phenyl)-2,5-diphenyl-cyclopentadienon；2,5-diphenyl-3,4-bis(4-fluorophenyl)cyclopentadienone；3,4-Bis(4-fluorophenyl)-2,5-diphenyl-2,4-cyclopentadien-1-one；3,4-bis(4-fluorophenyl)-2,5-diphenylcyclopenta-2,4-dien-1-one
• CAS: 56805-29-9
• 化学式: C₂₉H₁₈F₂O
• 分子量: 420.458
• InChiKey: VPXZKZUMSZRXCW-UHFFFAOYSA-N

物化性质

• 熔点：
  235.8-235.9 °C
• 沸点：
  621.8±55.0 °C(Predicted)
• 密度：
  1.278±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  32
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3,4-bis(4-fluorophenyl)-2,5-diphenylcyclopenta-2,4-dienone 在 lithium aluminium tetrahydride 、 三氯化铝 作用下， 以60%的产率得到2,3-Bis(4-fluorphenyl)-1,4-diphenyl-1,3-cyclopentadien
  参考文献：
  名称：

  Blum, Wolfgang; Franke, Helga; Richter, Wilhelm J., Chemische Berichte, 1983, vol. 116, p. 2931 - 2935

  摘要：

  DOI：
• 作为产物：
  描述：

  4,4'-二氟苯偶酰 、 二苄基甲酮 在 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以29%的产率得到3,4-bis(4-fluorophenyl)-2,5-diphenylcyclopenta-2,4-dienone
  参考文献：
  名称：

  Efficient Synthesis of Substituted Polyarylphthalimides via Cycloaddition of Cyclopentadienones with 2-Bromomaleimide

  摘要：

  已通过一步法合成了带有acenaphthene结构的功能化四芳基邻苯二甲酰亚胺或二芳基邻苯二甲酰亚胺。利用2-溴马来酰亚胺与四芳基环戊二烯酮（四环酮）或7,9-二芳基-8H-环戊并苊-8-酮（苊环酮）反应制得。该反应涉及环加成-脱羰基-脱溴化氢序列，具有高纯度产率，且能兼容多种官能团的存在。

  DOI：

  10.1055/s-0030-1260556

文献信息

• Efficient catalytic reduction of ketones with formic acid and ruthenium complexes
  作者：Naim Menashe、Einat Salant、Youval Shvo

  DOI：10.1016/0022-328x(95)05995-2

  日期：1996.5

  ring-substituted derivatives were found to act as efficient catalysts in reduction reactions of aldehydes and ketones to alcohols, using formic acid as H source. Excess formic acid accelerates the reaction, and the corresponding formate esters were isolated as sole products. Turnover numbers of up to 8000 (alcohols) and 11 000 (formate esters) were attained, with yields in the order of 90%. Alkenes are not reactive

  钌配合物（η 5 -C 4博士4 COHOC 4博士4 - η 5）（μ -H）（CO）4的Ru 2以甲酸为氢源，发现其苯环取代的衍生物可作为醛和酮还原为醇的有效催化剂。过量的甲酸会加速反应，并分离出相应的甲酸酯作为唯一产物。营业额高达8000（酒精）和11000（甲酸酯），产率约为90％。烯烃不具有反应性，但是，在反应条件下，与羰基共轭的双键被选择性地还原。该反应与多种酮相容，但是与脂族醛反应不是选择性的，因为形成了醇醛缩合产物。
• Thermal oxidation of tetracyclones (2,3,4,5-tetraarylcyclopentadienones)
  作者：Thies Thiemann、Jesus Iniesta、David J. Walton

  DOI：10.3184/030823408x310792

  日期：2008.3

  Tetracyclones are transformed to a mixture of diacylstilbenes and α-pyrones, when they are heated in diphenylether saturated with oxygen.

  当四旋风在氧饱和的二苯醚中加热时，它们会转化为二酰基二苯乙烯和 α-吡喃酮的混合物。
• Investigating the change in the photophysical properties of a trio of tetraphenylcyclopentadienone derivatives with varied groups on the aromatic rings in the 3‐ and 4‐positions
  作者：Arnoldo J. Orozco、Kole Joachim、Henry D. Ruiz、Frank R. Fronczek、Ralph Isovitsch

  DOI：10.1002/bio.3944

  日期：2021.2

  Such organic compounds can possess conjugation and/or aromatic systems, with one example being tetraphenylcyclopentadienone and its derivatives. A trio of dramatically coloured tetraphenylcyclopentadienone derivatives with varied substituents on the aromatic rings in the 3‐ and 4‐positions were prepared. Their identities were confirmed using the usual methods, for example 1H nuclear magnetic resonance

  具有电子特性（例如小带隙）的有机化合物可用于有机场效应晶体管到太阳能电池等领域。这样的有机化合物可以具有共轭和/或芳族体系，一个例子是四苯基环戊二烯酮及其衍生物。制备了三色的显色四苯基环戊二烯酮衍生物，这些衍生物在3位和4位芳香环上具有不同的取代基。使用常规方法（例如1 H核磁共振（NMR）光谱）确认其身份，并使用元素分析对其纯度进行定量。化合物2的X射线晶体结构被确定。它的显着结构特征涉及具有独特的C-C和C = C键长以及整体非平面性的环戊二烯酮核心，两者均有助于减轻其抗芳香性。化合物的氯仿溶液2 - 4展出吸收光谱具有三个吸收带在约250，350，和500nm已分配给（π）→（π*）的转换。计算化学方法有助于将观察到的跃迁分配给2 – 4结构中的特定分子轨道组合。从所有三种制备的化合物的氯仿溶液中观察到可见光谱的红色端（550-625 nm）的发射。
• 10.3184/030823408x298878
  作者：Iniesta, Jesus、Matsumoto, Taisuke、Thiemann, Thies

  DOI：10.3184/030823408x298878

  日期：——
• Catalytic disproportionation of aldehydes with ruthenium complexes
  作者：Naim Menashe、Youval Shvo

  DOI：10.1021/om00057a019

  日期：1991.11

  It was discovered that the ruthenium complex [(C4Ph4COHOCC4Ph4)(mu-H)][(CO)4Ru2] (2), as well as other isostructural Ru complexes, in the presence of a catalytic amount of formic acid, catalyzes the homogeneous bimolecular disproportionation reaction of aldehydes to give esters: 2RCHO --> RCOOCH2R. The reaction was found to be general and compatible with a variety of aliphatic and aromatic aldehydes and can be carried out in the presence or absence of solvent under mild conditions. It is characterized by an excellent efficiency with an initial turnover frequency reaching 5000 h-1, a measured overall turnover number of ca. 20 000, and high conversion, yield, and selectivity. Increasing the electron density on the metal and the ligand was found to accelerate the reaction. Kinetic studies indicate that the rate = k[catalyst]1/2[aldehyde]. The rate also depends on the initial formic acid concentration. A stoichiometric reaction of complex 2 with formic acid, monitored by infrared spectroscopy, shed light on the identity of the active catalytic species. No kinetic isotope effect could be detected by using PhCDO and DCOOD as reactants. Consequently, a mechanism and a detailed catalytic cycle for the bimolecular transformation of aldehydes to esters were proposed.