2-pentyl-3a,4,5,6,7,7a-hexahydro-4,7-methanoinden-1-one

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 2-pentyl-3a,4,5,6,7,7a-hexahydro-4,7-methanoinden-1-one
• 英文别名: (1S,2R,6R,7R)-4-pentyltricyclo[5.2.1.02,6]dec-4-en-3-one
• 化学式: C₁₅H₂₂O
• 分子量: 218.339
• InChiKey: ATBDLWVRGAYVHW-UVLXDEKHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.8
• 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：

  降冰片烯 、 1-庚炔 、 一氧化碳 在 cobalt(II) bromide 、 锌 作用下， 以 甲苯 、 叔丁醇 为溶剂， 以88%的产率得到2-pentyl-3a,4,5,6,7,7a-hexahydro-4,7-methanoinden-1-one
  参考文献：
  名称：

  Pauson-Khand反应的亚化学计量版本

  摘要：

  描述了一种使用炔烃Co 2（CO）6配合物的Pauson-Khand反应的新方案，该配合物是由一化学计量的CoBr 2和Zn在大气压的一氧化碳下制得的。

  DOI：

  10.1016/s0040-4039(98)02461-7

文献信息

• Advances in the cobalt-catalysed Pauson-Khand reaction: Development of a sulfide-promoted, microwave-assisted protocol
  作者：Alison R. Cochrane、William J. Kerr、Laura C. Paterson、Colin M. Pearson、Paul Shaw

  DOI：10.1016/j.tet.2020.131805

  日期：2021.1

  sulfide-promoted, microwave-assisted Pauson-Khand reaction has enabled the formation of fused cyclopentenones using sub-stoichiometric quantities of a cobalt mediator over rapid reaction times and with no requirement for an external source of toxic carbon monoxide gas. This protocol displays applicability to both intra- and intermolecular Pauson-Khand reaction examples.

  硫化物促进的微波辅助Pauson-Khand反应的发展使得能够在快速反应时间内使用亚化学计量的钴介体形成稠合的环戊烯酮，而无需外部有毒一氧化碳气体。该协议显示了适用于分子内和分子间的Pauson-Khand反应实例。
• Intermolecular Cobalt-Mediated Pauson-Khand Reactions in Ionic Liquids
  作者：Sabine Laschat、Armand Becheanu

  DOI：10.1055/s-2002-34892

  日期：——

  Intermolecular Pauson-Khand reactions of strained alkenes la-d with alkynes 2, 4, 6 and Co 2 (CO) 8 were performed in [bmim]PF 6 either thermally or in the presence of NMO. For comparison thermal reactions were done in toluene and NMO-promoted reactions in CH 2 Cl 2 . The results show that the ionic liquid is a suitable substitute for CH 2 Cl 2 . Yields of the NMO-promoted reaction could be improved

  应变烯烃la-d与炔烃2、4、6和Co 2 (CO) 8 的分子间Pauson-Khand反应在[bmim]PF 6 中以热方式或在NMO存在下进行。为了比较，在甲苯中进行热反应，在 CH 2 Cl 2 中进行 NMO 促进的反应。结果表明，该离子液体是CH 2 Cl 2 的合适替代品。NMO 促进反应的产率可以通过使用两相系统 [bmim]PF 6 /甲基环己烷来提高。
• A sub-stoichiometric version of the Pauson-Khand reaction
  作者：Thotapally Rajesh、Mariappan Periasamy

  DOI：10.1016/s0040-4039(98)02461-7

  日期：1999.1

  A new protocol for the Pauson-Khand reaction using alkyneCo2(CO)6 complexes prepared from sub-stoichiometric amounts of CoBr2 and Zn at atmospheric pressure of carbon monoxide is described.

  描述了一种使用炔烃Co 2（CO）6配合物的Pauson-Khand反应的新方案，该配合物是由一化学计量的CoBr 2和Zn在大气压的一氧化碳下制得的。
• A stable catalyst of the Pauson–Khand annelation
  作者：Susan E Gibson、Craig Johnstone、Andrea Stevenazzi

  DOI：10.1016/s0040-4020(02)00420-9

  日期：2002.6

  A practical catalytic-in-cobalt version of the PKA is clearly a desirable objective and there has been much research towards this goal in recent years. Systems developed to date, however, require either the use of high temperatures and high carbon monoxide pressures and/or the use of the sensitive cobalt catalyst, octacarbonyldieobablt(0). We report here a detailed account of PKA results obtained using the more robust cobalt compound, heptacarbonyl(triphenylphosphine)dicobalt(0), 1, which indicate that 1 is an attractive alternative to octacarbonyldicobalt(0) as a catalyst of the PKA. (C) 2002 Elsevier Science Ltd. All rights reserved.