(3aR,5R,11bR)-5-propyl-3,3a,5,11b-tetrahydro-2H-benzo[g]furo[3,2-c]isochromene-2,6,11-trione | 1093070-40-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异色满醌
• 英文名称: (3aR,5R,11bR)-5-propyl-3,3a,5,11b-tetrahydro-2H-benzo[g]furo[3,2-c]isochromene-2,6,11-trione
• 英文别名: (+)-7-deoxyfrenolicin B；7-Deoxyfrenolicin B；(11R,15R,17R)-17-propyl-12,16-dioxatetracyclo[8.7.0.03,8.011,15]heptadeca-1(10),3,5,7-tetraene-2,9,13-trione
• CAS: 1093070-40-6
• 化学式: C₁₈H₁₆O₅
• 分子量: 312.322
• InChiKey: AWQDEPOBZKVDQV-FMTVUPSXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (3aR,5R,11bR)-6,11-dimethoxy-5-propyl-3,3a,5,11b-tetrahydro-2H-benzo[g]furo[3,2-c]isochromen-2-one 在 ammonium cerium (IV) nitrate 作用下， 以 水 、 乙腈 为溶剂， 反应 0.17h， 以68%的产率得到(3aR,5R,11bR)-5-propyl-3,3a,5,11b-tetrahydro-2H-benzo[g]furo[3,2-c]isochromene-2,6,11-trione
  参考文献：
  名称：

  Direct Oxa-Pictet−Spengler Cyclization to the Natural (3a,5)-trans-Stereochemistry in the Syntheses of (+)-7-Deoxyfrenolicin B and (+)-7-Deoxykalafungin

  摘要：

  The pyranonaphthoquinones (+)-7-deoxyfrenolicin B and (+)-7-deoxykalafungin were synthesized in four steps using an oxa-Pictet-Spengler cyclization that directly provided the natural (3a,5)-trans-substituted dihydronaphthopyrans with high diastereoselectivity. This outcome is in contrast to the unnatural (3a,5)-cis-substituted dihydronaphthopyrans reported under similar conditions for the syntheses of (+)frenolicin B and (+)-kalafungin. Computational modeling is presented that provides insight into this unusual stereoselectivity.

  DOI：

  10.1021/jo801945n