| 1373131-87-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• CAS: 1373131-87-3
• 化学式: C₂₁H₂₂O₇
• 分子量: 386.401
• InChiKey: NNPCGDRETPLTQM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.74
• 重原子数：
  28.0
• 可旋转键数：
  1.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  72.45
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  甲醇 、 生成
  参考文献：
  名称：

  Oxidative Dimerization of (E)- and (Z)-2-Propenylsesamol with O₂ in the Presence and Absence of Laccases and Other Catalysts: Selective Formation of Carpanones and Benzopyrans under Different Reaction Conditions

  摘要：

  The oxidative dimerization of 2-propenylsesamol to carpanone with O-2 as the oxidant, which probably proceeds as a domino phenol oxidation/anti-beta,beta-radical coupling/intramolecular hetero Diets-Alder reaction, can be efficiently catalyzed by laccases. Experiments with laccases and other catalysts like a Co(salen) type catalyst and PdCl2 clearly demonstrate that the diastereoselectivity of the carpanone formation does not depend on the catalyst but on the double-bond geometry of the substrate. With (E)-2-propenylsesamol as the substrate, carpanone and a so far unknown carpanone diastereoisomer are formed in a 9:1 ratio. When (Z)-2-propenylsesamol is used as starting material, carpanone is accompanied by two carpanone diastereoisomers unknown so far in a 5:1:4 ratio. All three carpanone diastereoisomers have been separated by HPLC, and their structures have been elucidated unambiguously by NMR spectroscopy, DFT calculations, and spin work analysis. When the oxidation of 2-propenylsesamol with O-2 is performed in the absence of any catalyst two diastereoisomeric benzopyrans are formed, probably as the result of a domino oxidation/intermolecular hetero Diets-Alder reaction. Under these conditions, carpanone is formed in trace amounts only.

  DOI：

  10.1021/jo300263k