5-acetoxy-2,3,3a,4,5,7a-hexahydro-(3aα,5β,7aα)-benzofuran | 141612-37-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 5-acetoxy-2,3,3a,4,5,7a-hexahydro-(3aα,5β,7aα)-benzofuran
• CAS: 141612-37-5
• 化学式: C₁₀H₁₄O₃
• 分子量: 182.219
• InChiKey: RKLNHAOLCDWSFP-LPEHRKFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.28
• 重原子数：
  13.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  5-benzoyloxy-2,3,3a,4,5,7a-hexahydro-(3aα,5β,7aα)-benzofuran 在 氢氧化钾 、 水 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 5-acetoxy-2,3,3a,4,5,7a-hexahydro-(3aα,5β,7aα)-benzofuran
  参考文献：
  名称：

  Application of O2-DMSO as Reoxidant in the Pd(II)-Catalyzed 1,4-Oxidation of 5-Substituted 1,3-Cyclohexadienes.

  摘要：

  Palladium-catalyzed oxidation of 5-substituted 1,3-cyclohexadienes carrying a nucleophilic group in the side chain employing O-2-DMSO as the oxidant gave cyclization via 1,4-addition to the 1,3-diene. The nucleophilic groups employed were tosylamido and carboxy. In the reaction Pd-II is most likely reduced to colloidal Pd-0 which is subsequently reoxidized by O-2. The solvent DMSO prevents precipitation of metallic palladium by coordination to the colloidal particles. The stereochemistry of the palladium-catalyzed intramolecular 1,4-oxidation was controlled to some extent by the nature of the external nucleophile. Thus, in the intramolecular 1,4-oxyacyloxylation of 1 (hydroxy as nucleophile in the side chain) it was possible to direct the 1,4-addition towards cis or trans stereochemistry by variation of the external carboxylate nucleophile.

  DOI：

  10.3891/acta.chem.scand.51-0773

文献信息

• Bäckvall, Jan-E.; Andersson, Pher G., Journal of the American Chemical Society, 1992, vol. 114, # 16, p. 6374 - 6381
  作者：Bäckvall, Jan-E.、Andersson, Pher G.

  DOI：——

  日期：——