(5aS*,10bS*)-1H-2,3,4,5,5a,10b-hexahydro-9-hydroxybenzocycloheptafuran-4-one | 126665-94-9

• 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: (5aS*,10bS*)-1H-2,3,4,5,5a,10b-hexahydro-9-hydroxybenzocycloheptafuran-4-one
• CAS: 126665-94-9
• 化学式: C₁₃H₁₄O₃
• 分子量: 218.252
• InChiKey: AUDMUUIWTGYTCI-GWCFXTLKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.38
• 重原子数：
  16.0
• 可旋转键数：
  0.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  1-methoxy-1,3-cycloheptadiene 在 盐酸 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 25.0h， 生成 (5aS*,10bS*)-1H-2,3,4,5,5a,10b-hexahydro-9-hydroxybenzocycloheptafuran-4-one
  参考文献：
  名称：

  Controlling the stereochemistry of the ring junction in hexahydrodibenzofurans

  摘要：

  The 8-hydroxy-1,2,3,4,4a,9b-hexahydrodibenzofuran-3-one formed during the acid-catalyzed rearrangement of 1,4,4a,8a-tetrahydro-1-methoxy-1,4-ethanonaphthalene-5,8-dione is, contrary to published reports, exclusively the cis isomer by X-ray crystallography. The stereochemical outcome of this intramolecular Michael addition results from the cyclid nature of the alpha,beta-unsaturated carbonyl, since, in acyclic systems, the addition product is a trans-2,3-disubstituted 2,3-dihydrobenzofuran. The trans relationship of the 2- and 3-substituents in the acyclic system was confirmed by annulation to the trans-8-hydroxy-1,2,3,4,4a,9b-hexahydrodibenzofuran-3-one and X-ray crystallographic analysis of the 3-cyanohydrin.

  DOI：

  10.1021/jo00021a042