(3aR,5R,11bR)-6,11-dimethoxy-5-propyl-3,3a,5,11b-tetrahydro-2H-benzo[g]furo[3,2-c]isochromen-2-one | 1093070-43-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: (3aR,5R,11bR)-6,11-dimethoxy-5-propyl-3,3a,5,11b-tetrahydro-2H-benzo[g]furo[3,2-c]isochromen-2-one
• 英文别名: (11R,15R,17R)-2,9-dimethoxy-17-propyl-12,16-dioxatetracyclo[8.7.0.03,8.011,15]heptadeca-1,3,5,7,9-pentaen-13-one
• CAS: 1093070-43-9
• 化学式: C₂₀H₂₂O₅
• 分子量: 342.392
• InChiKey: SQUSUABOPBTXET-JZKQVHKSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  正丁醛 、 2-<(2'R,3'R)-3'-hydroxy-5'-oxotetrahydrofuran-2'-yl>-1,4-dimethoxynaphthalene 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 以88%的产率得到(3aR,5R,11bR)-6,11-dimethoxy-5-propyl-3,3a,5,11b-tetrahydro-2H-benzo[g]furo[3,2-c]isochromen-2-one
  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

文献信息

• Direct Oxa-Pictet−Spengler Cyclization to the Natural (3a,5)-<i>trans</i>-Stereochemistry in the Syntheses of (+)-7-Deoxyfrenolicin B and (+)-7-Deoxykalafungin
  作者：Clark N. Eid、Jaechul Shim、Jack Bikker、Melissa Lin

  DOI：10.1021/jo801945n

  日期：2009.1.2

  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.