bis(2-methoxy-4-allylphenyl)oxalate

• 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: bis(2-methoxy-4-allylphenyl)oxalate
• 英文别名: bis(eugenol) oxalate；Eugenyl oxalate；bis(2-methoxy-4-prop-2-enylphenyl) oxalate
• 化学式: C₂₂H₂₂O₆
• 分子量: 382.413
• InChiKey: QQUHEFABALZOST-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  28
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  bis(2-methoxy-4-allylphenyl)oxalate 在 双氧水 作用下， 生成 丁香酚
  参考文献：
  名称：

  Bifunctional Aryloxylate Esters as potential oxidatively cleavable linkers

  摘要：

  Selectively cleavable linkers are essential parts in environmentally responsive materials. Here, we introduce aryl oxalate esters (AOE) as one of the first examples for oxidatively cleavable linkers. To this end a series of novel AOEs was synthesized and explored regarding the H2O2-dependent degradation. All AOEs were cleaved selectively at the oxalate group. The degradation rate was clearly dependent on the substituents. Further, it was found that the H2O2 based degradation undergoes an autocatalysis mechanism. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.04.083
• 作为产物：
  描述：

  草酰氯 、 丁香酚 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以90%的产率得到bis(2-methoxy-4-allylphenyl)oxalate
  参考文献：
  名称：

  Theoretical and experimental investigations on molecular structure of bis(2-methoxy-4-allylphenyl)oxalate

  摘要：

  The aim of this study is to find out the molecular characteristic and structural parameters that govern the chemical behavior of a new bis(2-methoxy-4-allylphenyl)oxalate compound and to compare predictions made from theory with experimental observations. The title compound, bis(2-methoxy-4-allylphenyl) oxalate (I), (C22H22O6), has been synthesized. The compound has been characterized by elemental analysis, IR, H-1 NMR, C-13 NMR spectroscopies and single crystal X-ray diffraction techniques. Optimized molecular structure, harmonic vibrational frequencies have been calculated by B3LYP/6-311G(d,p) method using density functional theory (DFT). H-1 and C-13 nuclear magnetic resonance (NMR) chemical shifts of the molecule have been investigated by the Gauge-Invariant Atomic Orbital (GIAO) method. The calculated results show that the predicted geometry can well reproduce structural parameters. To estimate chemical reactive sites of the molecule, molecular electrostatic potential map (MEP), frontier molecular orbitals (FMOs), Mulliken population method and natural population analysis (NPA) have been calculated for the optimized geometry of the molecule. To investigate the NW properties of the molecule, the electric dipole, the polarizability and the first hyperpolarizability have been calculated. In addition, thermodynamic properties have also been studied. (C) 2015 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2015.09.009