3-cyano-2,5,6-trimethylanisole | 876389-25-2

• 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: 3-cyano-2,5,6-trimethylanisole
• 英文别名: 3-Methoxy-2,4,5-trimethylbenzonitrile
• CAS: 876389-25-2
• 化学式: C₁₁H₁₃NO
• mdl: MFCD09032419
• 分子量: 175.23
• InChiKey: XVTRJTCWISNTMW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.363
• 拓扑面积：
  33
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-cyano-2,5,6-trimethylanisole 在 氢氧化钾 、 lithium aluminium tetrahydride 、 乙二醇 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 27.0h， 生成 3-methoxy-2,4,5-trimethylbenzyl alcohol
  参考文献：
  名称：

  Synthesis and Antioxidant Profile of all-rac-α-Selenotocopherol

  摘要：

  all-rac-alpha-Selenotocopherol (6c) has been synthesized in 11 steps in 6.6% total yield. Key steps include chloromethylation to approach the persubstituted aromatic 9b and cyclization of alcohol precursor 10 by radical homolytic substitution at selenium to form the selenotocopherol heterocycle. Determination of the OH bond dissociation enthalpy (BDE) of 6c by electron paramagnetic resonance (EPR) equilibration techniques gave a value of 78.1 +/- 0.3 kcal mol(-1), approximately I kcal mol(-1) higher than that of a-tocopherol. Kinetic studies performed by measuring oxygen uptake of the induced oxidation of styrene in the presence of an antioxidant showed that selenotocopherol (6c) was a slightly poorer inhibitor than (x-tocopherol, in agreement with the BDE values. In contrast to simpler setenotocopherol analogues, 6c was not regenerable in the presence of a stoichiometric coreductant in a two-phase lipid peroxidation model.

  DOI：

  10.1021/jo052133e
• 作为产物：
  描述：

  2,3,6-三甲基苯酚 在 lead(IV) acetate 、 potassium carbonate 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 22.67h， 生成 3-cyano-2,5,6-trimethylanisole
  参考文献：
  名称：

  Synthesis and Antioxidant Profile of all-rac-α-Selenotocopherol

  摘要：

  all-rac-alpha-Selenotocopherol (6c) has been synthesized in 11 steps in 6.6% total yield. Key steps include chloromethylation to approach the persubstituted aromatic 9b and cyclization of alcohol precursor 10 by radical homolytic substitution at selenium to form the selenotocopherol heterocycle. Determination of the OH bond dissociation enthalpy (BDE) of 6c by electron paramagnetic resonance (EPR) equilibration techniques gave a value of 78.1 +/- 0.3 kcal mol(-1), approximately I kcal mol(-1) higher than that of a-tocopherol. Kinetic studies performed by measuring oxygen uptake of the induced oxidation of styrene in the presence of an antioxidant showed that selenotocopherol (6c) was a slightly poorer inhibitor than (x-tocopherol, in agreement with the BDE values. In contrast to simpler setenotocopherol analogues, 6c was not regenerable in the presence of a stoichiometric coreductant in a two-phase lipid peroxidation model.

  DOI：

  10.1021/jo052133e