(4aR*,9bS*)-1,2,3,4,4a,9b-hexahydro-8-hydroxydibenzofuran-3-one | 126665-92-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 香豆素
• 英文名称: (4aR*,9bS*)-1,2,3,4,4a,9b-hexahydro-8-hydroxydibenzofuran-3-one
• 英文别名: (4aR,9bS)-8-hydroxy-2,4,4a,9b-tetrahydro-1H-dibenzofuran-3-one
• CAS: 126665-92-7
• 化学式: C₁₂H₁₂O₃
• 分子量: 204.225
• InChiKey: RDOLAFNIEXUXQM-JOYOIKCWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (4aR*,9bS*)-3-hydroxy-1,2,3,4,4a,9b-hexahydro-8-hydroxydibenzofuran-3-carbonitrile 在 二甲基亚砜 作用下， 45.0 ℃ 、13.33 Pa 条件下， 反应 0.33h， 以63%的产率得到(4aR*,9bS*)-1,2,3,4,4a,9b-hexahydro-8-hydroxydibenzofuran-3-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

文献信息

• US4978679A
  申请人：——

  公开号：US4978679A

  公开（公告）日：1990-12-18
• Controlling the stereochemistry of the ring junction in hexahydrodibenzofurans
  作者：Kathleen M. Rupprecht、Joshua Boger、Karst Hoogsteen、Robert B. Nachbar、James P. Springer

  DOI：10.1021/jo00021a042

  日期：1991.10

  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.