3-ferrocenyl-2,4,5-triphenylcyclopentadienone | 12310-16-6

• 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-ferrocenyl-2,4,5-triphenylcyclopentadienone
• 英文别名: cyclopenta-1,3-diene;3-cyclopenta-1,4-dien-1-yl-2,4,5-triphenylcyclopenta-2,4-dien-1-one;iron(2+)
• CAS: 12310-16-6
• 化学式: C₃₃H₂₄FeO
• 分子量: 492.4
• InChiKey: QJKFAVMQMBNLQE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  None
• 重原子数：
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• 可旋转键数：
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• 环数：
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• sp3杂化的碳原子比例：
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• 拓扑面积：
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• 氢给体数：
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• 氢受体数：
  None

反应信息

• 作为反应物：
  描述：

  diiron nonacarbonyl 、 3-ferrocenyl-2,4,5-triphenylcyclopentadienone 以 四氢呋喃 为溶剂， 以58%的产率得到(3-ferrocenyl-2,4,5-triphenylcyclopentadienone)tricarbonyliron
  参考文献：
  名称：

  四旋管和3-二茂铁基-2,4,5-三苯基环戊二烯酮的乙酰丙酮铑和三羰基铁配合物：X射线晶体学和NMR研究

  摘要：

  四环气旋与Fe 2（CO）9和（acac）Rh（C 2 H 4）2反应得到（C 4 Ph 4 C O）Fe（CO）3（3）和（C 4 Ph 4 C O）Rh （acac）（11）。同样，3-二茂铁基-2,3,4-三苯基环戊二烯酮（2）产生（C 4 Ph 3 FcCO ）Fe（CO）3（7）和（C 4 Ph 3 FcCO ）Rh（acac）（14）。在3，外围苯基取代基采用固态的螺旋桨构象，并且对Fe（CO）3片段的通量性的阻隔很低，以至于无法观察到低温下三脚架旋转变慢。相反，二茂铁基类似物7显示出受限制的三脚架旋转，但这可能是由于庞大的二茂铁基取代基引起空间位阻的结果。在晶体中，（四旋风）Rh（acac）（11）以头对尾二聚体的形式存在，其中铑中心键合至分子另一半中的乙酰丙酮酸酯配体的γ-碳。二茂铁基类似物14在固态和在溶液中都是单体，Rh（acac）片段的旋转势垒被评估为12 kcal mol

  DOI：

  10.1021/om990559b

文献信息

• Diels−Alder Reactions of 3-Ferrocenyl-2,4,5-triphenylcyclopentadienone:  Syntheses and Structures of the Sterically Crowded Systems C₆Ph₅Fc, C₇Ph₆FcH, and [C₇Ph₆FcH][SbCl₆]
  作者：Hari K. Gupta、Stacey Brydges、Michael J. McGlinchey

  DOI：10.1021/om980645w

  日期：1999.1.1

  Diels-Alder addition of diphenylacetylene or of 1,2,3-triphenylcyclopropene to 3-ferrocenyl-2,4,5-triphenylcyclopentadienone yields, upon thermolysis, C(6)Ph(5)Fc (5) or C(7)Ph(6)FcH (8), respectively. Subsequent treatment of 8 with triethyloxonium hexachloroantimonate results in the formation of the ferricinium complex [C(7)Ph(6)FcH](+)[SbCl6](-) (13), rather than the anticipated tropylium cation [C(7)Ph(6)Fc](+). The substituted ferrocene derivatives 5, 8, and 13 have been characterized by X-ray crystallography. From the solid-state structure of 5 it is evident that the peripheral aryl substituents do not adopt a regular propeller type conformation, but instead exhibit an incremental progression of twist angles relative to the central ring. The dynamics of peripheral ring rotations in 5 and 8 have been studied by variable-temperature NMR.
• Spectroscopic and Computational Assessment of the Rotational Barrier of a Ferrocenyl-Stabilized Cyclopentadienyl Cation:  Evidence for the First Hydroxyfulvalene Ligand
  作者：Laura E. Harrington、Ignacio Vargas-Baca、Nada Reginato、Michael J. McGlinchey

  DOI：10.1021/om020820f

  日期：2003.2.1

  Protonation of 3-ferrocenyl-2,4,5-triphenylcyclopentadienone with trifluoroacetic acid results in the formation of the first hydroxyfulvalene complex. The dramatic deshielding and decoaleseence of the H-1 and C-13 NMR signals in the ferrocenyl region offer evidence for the participation of the metal in the stabilization of the positive charge, which results in restricted rotation of the ferrocenyl group. As determined by NMR spectroscopy, the maximum barrier to rotation in the neutral species is ca. 9 kcal mol(-1), whereas the minimum barrier in the cation considerably exceeds 13 kcal mol(-1). The difference in rotational barriers for the neutral and protonated species is rationalized by using DFT calculations.