Pent-3-ynyl undec-9-ynoate | 255381-55-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: Pent-3-ynyl undec-9-ynoate
• CAS: 255381-55-6
• 化学式: C₁₆H₂₄O₂
• 分子量: 248.365
• InChiKey: VMTFHGZZRRSXTL-UHFFFAOYSA-N

物化性质

• 沸点：
  345.1±27.0 °C(Predicted)
• 密度：
  0.945±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  18
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Pent-3-ynyl undec-9-ynoate 在 Lindlar's catalyst hexacarbonyl molybdenum 、 氢气 、 对氯苯酚 作用下， 以 various solvent(s) 为溶剂， 生成 氧杂环十三烷-2-酮
  参考文献：
  名称：

  Fürstner, Alois; Guth, Oliver; Rumbo, Antonio, Journal of the American Chemical Society, 1999, vol. 121, # 48, p. 11108 - 11113

  摘要：

  DOI：
• 作为产物：
  描述：

  9-十一碳炔-1-醇 在 重铬酸吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 Pent-3-ynyl undec-9-ynoate
  参考文献：
  名称：

  Fürstner, Alois; Guth, Oliver; Rumbo, Antonio, Journal of the American Chemical Society, 1999, vol. 121, # 48, p. 11108 - 11113

  摘要：

  DOI：

文献信息

• ¹⁸³ W NMR Spectroscopy Guides the Search for Tungsten Alkylidyne Catalysts for Alkyne Metathesis
  作者：Julius Hillenbrand、Markus Leutzsch、Christopher P. Gordon、Christophe Copéret、Alois Fürstner

  DOI：10.1002/anie.202009975

  日期：2020.11.23

  Triarylsilanolates are privileged ancillary ligands for molybdenum alkylidyne catalysts for alkyne metathesis but lead to disappointing results and poor stability in the tungsten series. 1H,183W heteronuclear multiple bond correlation spectroscopy, exploiting a favorable 5J‐coupling between the 183W center and the peripheral protons on the alkylidyne cap, revealed that these ligands upregulate the Lewis acidity

  三芳基硅烷醇盐是用于炔复分解的钼亚烷基催化剂的优先辅助配体，但在钨系列中导致令人失望的结果和较差的稳定性。1 H, 183 W 异核多重键相关光谱，利用183 W 中心与烷叉帽上的外围质子之间有利的5 J耦合，揭示了这些配体将路易斯酸度上调到一定程度，使得环丁二烯钨在最初形成[2+2]环加成步骤过度稳定并且催化周转停止。以183 W NMR 位移作为中心原子路易斯酸度的代表，并通过烷叉单元的化学位移张量分析，重新审视了配体设计，并制备了更强的 π 供体全醇盐配体。新的膨胀螯合物具有缓和的路易斯酸度，并且在速率和官能团相容性方面优于带有单齿叔丁氧基配体的经典Schrock催化剂。
• Alkyne Metathesis with d²Re(V) Alkylidyne Complexes Supported by Phosphino-Phenolates: Ligand Effect on Catalytic Activity and Applications in Ring-Closing Alkyne Metathesis
  作者：Mingxu Cui、Herman H. Y. Sung、Ian D. Williams、Guochen Jia

  DOI：10.1021/jacs.2c00368

  日期：2022.4.13

  Re(V) alkylidyne complexes bearing two decorated phosphino-phenolates (POs) and a labile pyridine ligand were prepared that can efficiently promote alkyne metathesis reactions in toluene. The relative activity of these complexes varies with the PO ligands. Complexes with an electron-rich metal center have a higher activity. Ligand exchange experiments suggest that the pyridine ligands of the Re(V) alkylidynes

  A family of d2 Re(V) alkylidyne complexes bearing two decorated phosphino-phenolates (POs) and a labile pyridine ligand were prepared that can efficiently promote alkyne metathesis reactions in toluene. The relative activity of these complexes varies with the PO ligands. Complexes with an electron-rich metal center have a higher activity. Ligand exchange experiments suggest that the pyridine ligands
• An Improved Catalyst for Ring-Closing Alkyne Metathesis Based on Molybdenum Hexacarbonyl/2-Fluorophenol
  作者：Karol Grela、Jolanta Ignatowska

  DOI：10.1021/ol026690o

  日期：2002.10.1

  improved "instant" catalyst for ring-closing alkyne metathesis reaction is described. Catalyst formed in situ from molybdenum hexacarbonyl and 2-fluorophenol can be used without exclusion of air and moisture and shows high activity in metathesis of functionalized diynes. This system allows cyclization of substrates which were incompatible with previously known Mo(CO)(6)/phenol catalysts.

  [反应：见正文]描述了一种用于闭环炔烃复分解反应的改进的“即时”催化剂。由六羰基钼和2-氟苯酚原位形成的催化剂可以在不排除空气和水分的情况下使用，并且在官能化二炔的复分解反应中表现出很高的活性。该系统允许与先前已知的Mo（CO）（6）/苯酚催化剂不相容的底物环化。