1-(10-(diethoxyphosphoryl)decyl)-3-methylimidazolium bis(trifluoromethanesulfonyl)imide | 1459783-03-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物
• 英文名称: 1-(10-(diethoxyphosphoryl)decyl)-3-methylimidazolium bis(trifluoromethanesulfonyl)imide
• CAS: 1459783-03-9
• 化学式: C₂F₆NO₄S₂*C₁₈H₃₆N₂O₃P
• 分子量: 639.618
• InChiKey: WDWCSNPWKAPMMP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.76
• 重原子数：
  39.0
• 可旋转键数：
  17.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  126.72
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  1,10-二溴癸烷 以 二氯甲烷 、 水 为溶剂， 反应 30.0h， 生成 1-(10-(diethoxyphosphoryl)decyl)-3-methylimidazolium bis(trifluoromethanesulfonyl)imide
  参考文献：
  名称：

  Interfacial Electric Field Effects on a Carbene Reaction Catalyzed by Rh Porphyrins

  摘要：

  An intramolecular reaction catalyzed by Rh porphyrins was studied in the presence of interfacial electric fields. 1-Diazo-3,3-dimethyl-5-phenylhex-5-en-2-one (2) reacts with Rh porphyrins via a putative carbenoid intermediate to form cyclopropanation product 3,3-dimethyl-5-phenylbicyclo[3.1.0]hexan-2-one (3) and insertion product 3,3-dimethyl-2,3-dihydro-[1,1'-biphenyl]-4(1H)-one (4). To study this reaction in the presence of an interfacial electric field, Si electrodes coated with thin films of insulating dielectric layers were used as the opposing walls of a reaction vessel, and Rh porphyrin catalysts were localized to the dielectric electrolyte-interface. The charge density was varied at the interface by changing the voltage across the two electrodes. The product ratio was analyzed as a function of the applied voltage and the surface chemistry of the dielectric layer. In the absence of an applied voltage, the ratio of 3:4 was approximately 10:1. With a TiO2 surface, application of a voltage induced a Rh porphyrin-TiO2 interaction that resulted in an increase in the 3:4 ratio to a maximum in which 4 was nearly completely suppressed (>100:1). With an Al2O3 surface or an alkylphosphonate-coated surface, the voltage caused a decrease in the 3:4 ratio, with a maximum effect of lowering the ratio to 1:2. The voltage-induced decrease in the 3:4 ratio in the absence of TiO2 was consistent with a field-dipole effect that changed the difference in activation energies for the product-determining step to favor product 4. Effects were observed for porphyrin catalysts localized to the electrode-electrolyte interface either through covalent attachment or surface adsorption, enabling the selectivity to be controlled with unfunctionalized Rh porphyrins. The magnitude of the selectivity change was limited by the maximum interfacial charge density that could be attained before dielectric breakdown.

  DOI：

  10.1021/ja404394z

文献信息

• Click chemistry mediated synthesis of bio-inspired phosphonyl-functionalized ionic liquids
  作者：Richard A. Braun、Joseph L. Bradfield、Codey B. Henderson、Niloufar Mobarrez、Yinghong Sheng、Richard A. O'Brien、Alexandra C. Stenson、James H. Davis、Arsalan Mirjafari

  DOI：10.1039/c4gc01933d

  日期：——

  The key objective of this work is to develop bio-inspired ionic liquids that are highly lipophilic via “click” chemistry.

  这项工作的关键目标是通过“点击”化学方法开发高脂溶性的仿生离子液体。