1-methoxy-3-phenylbut-3-en-2-ol | 1611454-56-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醇
• 英文名称: 1-methoxy-3-phenylbut-3-en-2-ol
• CAS: 1611454-56-8
• 化学式: C₁₁H₁₄O₂
• 分子量: 178.231
• InChiKey: OZLVCUFFULEECP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.71
• 重原子数：
  13.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  29.46
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  trans-(3-phenylcyclopropyl)methanol 在 氧气 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 50.0 ℃ 、101.33 kPa 条件下， 生成 1-methoxy-3-phenylbut-3-en-2-yl benzoate 、 1-methoxy-3-phenylbut-3-en-2-ol
  参考文献：
  名称：

  Dehydrogenative α-Oxygenation of Ethers with an Iron Catalyst

  摘要：

  Selective alpha-oxidation of ethers under aerobic conditions is a long-pursued transformation; however, a green and efficient catalytic version of this reaction remains challenging. Herein, we report a new family of iron catalysts capable of promoting chemoselective alpha-oxidation of a range of ethers with excellent mass balance and high turnover numbers under 1 atm of O-2 with no need for any additives. Unlike metalloenzymes and related biomimetics, the catalyst produces H-2 as the only byproduct. Mechanistic investigations provide evidence for an unexpected two-step reaction pathway, which involves dehydrogenative incorporation of O-2 into the ether to give a peroxobisether intermediate followed by cleavage of the peroxy bond to form two ester molecules, releasing stoichiometric H-2 gas in each step. The operational simplicity and environmental friendliness of this methodology affords a useful alternative for performing oxidation, while the unique ability of the catalyst in oxygenating a substrate via dehydrogenation points to a new direction for understanding metalloenzymes and designing new biomimetic catalysts.

  DOI：

  10.1021/ja502167h