2-phenyl-3a,4,7,7a-tetrahydro-1H-4,7-methanoinden-1-one | 204757-66-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-phenyl-3a,4,7,7a-tetrahydro-1H-4,7-methanoinden-1-one
• 英文别名: 4-phenyltricyclo[5.2.1.02,6]deca-4,8-dien-3-one
• CAS: 204757-66-4
• 化学式: C₁₆H₁₄O
• 分子量: 222.287
• InChiKey: KDWMMOJCADYEKA-UHFFFAOYSA-N

物化性质

• 沸点：
  395.3±42.0 °C(Predicted)
• 密度：
  1.203±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  一氧化碳 、 2,5-降冰片二烯 、 苯乙炔 在 四甲基硫脲 、 cobalt(II) bromide 、 锌 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以76%的产率得到2-phenyl-3a,4,7,7a-tetrahydro-1H-4,7-methanoinden-1-one
  参考文献：
  名称：

  CoBr2–TMTU–zinc catalysed-Pauson–Khand reaction

  摘要：

  一种钴-TMTU复合物，由CoBr2在TMTU存在下与锌原位还原得到，可以催化在二氧化碳气球压力下进行Pauson-Khand反应，从而合成结构多样的环戊烯酮。该催化系统对分子间和分子内的PK反应均有效。

  DOI：

  10.1039/c2cc17971g

文献信息

• Synthesis, Coordination Study, and Catalytic Pauson–Khand Reactions of QuinoxP*(CO)₄-μ-Alkyne Dicobalt Complexes
  作者：Martí Garçon、Albert Cabré、Xavier Verdaguer、Antoni Riera

  DOI：10.1021/acs.organomet.7b00018

  日期：2017.3.13

  The coordination of the P-stereogenic and sterically demanding bisphosphine QuinoxP* to mu-alkyne dicobalt hexacarbonyl complexes was studied experimentally and computationally. 'Whereas the coordination occurred exclusively in a chelating fashion, the diastereoselectivity was highly substrate dependent. However, it could be explained from the computed structure and energies of the different coordination modes. The fluxional behavior of these complexes was also studied computationally. Their performance as catalysts for the Pauson-Khand reaction was explored, and outstanding reactivity was observed. Although the asymmetric induction was low to "moderate, the stereochemical outcome could be mechanistically rationalized. This report provides promising results in terms of reactivity and mechanistic understanding for further developments of highly active chiral catalysts for intermolecular Pauson Khand reactions.
• Cobalt Nanoparticles on Charcoal:  A Versatile Catalyst in the Pauson−Khand Reaction, Hydrogenation, and the Reductive Pauson−Khand Reaction
  作者：Seung Uk Son、Kang Hyun Park、Young Keun Chung

  DOI：10.1021/ol0268889

  日期：2002.10.1

  [GRAPHICS]Dispersions of nanometer-sized cobalt particles with very high stability were prepared in charcoal and analyzed by electron microscopy and X-ray analysis. The resulting cobalt nanoparticles on charcoal (CNC) were successfully used as a catalyst for the carbonylative cycloaddition of alkyne, alkene, and carbon monoxide (Pauson-Khand reaction), hydrogenation, and the reductive Pauson-Khand reaction.
• Cobalt on Mesoporous Silica:  The First Heterogeneous Pauson−Khand Catalyst
  作者：Sang-Wook Kim、Seung Uk Son、Sang Ick Lee、Taeghwan Hyeon、Young Keun Chung

  DOI：10.1021/ja9939237

  日期：2000.2.1
• ——
  作者：Sang-Wook Kim、Seung Uk Son、Su Seong Lee、Taeghwan Hyeon、Young Keun Chung

  DOI：10.1039/b107577m

  日期：2001.10.23

  A new Pauson-Khand catalyst based on colloidal cobalt nanoparticles has been developed; the catalyst is highly effective for many intra- and inter-molecular Pauson-Khand reactions and can be recycled and reused many times without losing catalytic activity.
• The Pauson−Khand Reaction Catalyzed by the Methylidynetricobalt Nonacarbonyl Cluster
  作者：Takumichi Sugihara、Masahiko Yamaguchi

  DOI：10.1021/ja982635s

  日期：1998.10.1