5,18:9,14-di<1',2'>benzeno-5,6,6a,7,9,14,14a,14b,15,18,-decahydronaphtho<2,3-c>pentaphene-6,15-dione | 136954-37-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 并四苯
• 英文名称: 5,18:9,14-di<1',2'>benzeno-5,6,6a,7,9,14,14a,14b,15,18,-decahydronaphtho<2,3-c>pentaphene-6,15-dione
• 英文别名: 5,18:9,14-di[1',2']benzeno-5,6,6a,7,9,14,14a,14b,15,18,-decahydronaphtho[2,3-c]pentaphene-6,15-dione
• CAS: 136954-37-5
• 化学式: C₄₂H₂₈O₂
• 分子量: 564.683
• InChiKey: BWWPSKZQAQNMTK-GSEVDFHSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.52
• 重原子数：
  44.0
• 可旋转键数：
  0.0
• 环数：
  13.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  34.14
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  5,18:9,14-di<1',2'>benzeno-5,6,6a,7,9,14,14a,14b,15,18,-decahydronaphtho<2,3-c>pentaphene-6,15-dione 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 四氯化碳 为溶剂， 反应 24.0h， 以74%的产率得到5,18:9,14-di<1',2'>benzeno-5,6,9,14,15,18-hexahydronaphtho<2,3-c>pentaphene-6,15-dione
  参考文献：
  名称：

  Synthesis of three helically chiral iptycenes

  摘要：

  The synthesis of iptycenes 2-4, each of which is helically chiral and has a C2 symmetry axis, is described. Key intermediates are diene 7, prepared in two steps and 44% yield from known ketone 5, and anthracene 11, prepared in four steps and 48% yield from diene 7. A noteworthy step in the latter sequence is the aluminum chloride catalyzed, room-temperature, regio- and stereoselective cycloaddition of naphthoquinone 8 to diene 7 to give a single isomer of 9. Anthracene 11 was converted in one step to 2 and in four steps to 3 (Scheme II). Bicycloalkene 15, an intermediate in the latter synthesis, was converted to 4 in two steps (Scheme III). Cycloaddition of unactivated dienophile 15 to unactivated dienes 17 and 18 proceeds in good yields. Hydrocarbon 3 could be resolved on several chiral columns.

  DOI：

  10.1021/jo00024a038
• 作为产物：
  描述：

  9,10-dihydro-9,10-ethano-anthracen-11-one 在 三氯化铝 、 phosphorus pentoxide 作用下， 以 四氢呋喃 、 正庚烷 、 二氯甲烷 、 xylene 为溶剂， 反应 125.0h， 生成 5,18:9,14-di<1',2'>benzeno-5,6,6a,7,9,14,14a,14b,15,18,-decahydronaphtho<2,3-c>pentaphene-6,15-dione
  参考文献：
  名称：

  Synthesis of three helically chiral iptycenes

  摘要：

  The synthesis of iptycenes 2-4, each of which is helically chiral and has a C2 symmetry axis, is described. Key intermediates are diene 7, prepared in two steps and 44% yield from known ketone 5, and anthracene 11, prepared in four steps and 48% yield from diene 7. A noteworthy step in the latter sequence is the aluminum chloride catalyzed, room-temperature, regio- and stereoselective cycloaddition of naphthoquinone 8 to diene 7 to give a single isomer of 9. Anthracene 11 was converted in one step to 2 and in four steps to 3 (Scheme II). Bicycloalkene 15, an intermediate in the latter synthesis, was converted to 4 in two steps (Scheme III). Cycloaddition of unactivated dienophile 15 to unactivated dienes 17 and 18 proceeds in good yields. Hydrocarbon 3 could be resolved on several chiral columns.

  DOI：

  10.1021/jo00024a038