5,18:8,17:9,14-tri<1',2'>benzeno-5,8,9,14,17,18-hexahydronaphtho<2,3-c>pentaphene | 136954-31-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 5,18:8,17:9,14-tri<1',2'>benzeno-5,8,9,14,17,18-hexahydronaphtho<2,3-c>pentaphene
• 英文别名: tridecacyclo[14.14.6.64,11.619,26.02,15.03,12.05,10.017,30.018,27.020,25.031,36.037,42.043,48]octatetraconta-2(15),3(12),5,7,9,13,17(30),18(27),20,22,24,28,31,33,35,37,39,41,43,45,47-henicosaene
• CAS: 136954-31-9
• 化学式: C₄₈H₃₀
• 分子量: 606.766
• InChiKey: OZAQKILIJPYUFU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.65
• 重原子数：
  48.0
• 可旋转键数：
  0.0
• 环数：
  16.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为产物：
  描述：

  2-carboxybenzene diazonium chloride 、 5,18:9,14-di<1',2'>benzeno-5,9,14,18-tetrahydronaphtho<2,3-c>pentaphene 在 methyloxirane 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 12.0h， 以60%的产率得到5,18:8,17:9,14-tri<1',2'>benzeno-5,8,9,14,17,18-hexahydronaphtho<2,3-c>pentaphene
  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