noniptycene | 136954-32-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: noniptycene
• 英文别名: heptadecacyclo[14.14.14.64,11.619,26.634,41.02,15.03,12.05,10.017,30.018,27.020,25.031,44.033,42.035,40.045,50.051,56.057,62]dohexaconta-2(15),3(12),5,7,9,13,17(30),18(27),20,22,24,28,31(44),32,35,37,39,42,45,47,49,51,53,55,57,59,61-heptacosaene
• CAS: 136954-32-0
• 化学式: C₆₂H₃₈
• 分子量: 782.984
• InChiKey: RVMKHSVJIBVNJN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.5
• 重原子数：
  62
• 可旋转键数：
  0
• 环数：
  21.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 苯 为溶剂， 反应 24.0h， 以99%的产率得到noniptycene
  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