(+)-(P)-11,12-benzo-2-(1-adamantylamino)-1-aza[6]helicene

• 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: (+)-(P)-11,12-benzo-2-(1-adamantylamino)-1-aza[6]helicene
• 英文别名: N-(1-adamantyl)-5-azaheptacyclo[16.12.0.02,15.03,12.04,9.019,24.025,30]triaconta-1(18),2(15),3(12),4(9),5,7,10,13,16,19,21,23,25,27,29-pentadecaen-6-amine
• 化学式: C₃₉H₃₂N₂
• 分子量: 528.696
• InChiKey: RFGPNTOXUFHKOY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.6
• 重原子数：
  41
• 可旋转键数：
  2
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  24.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (+)-(P)-11,12-benzo-2-(1-adamantylamino)-1-aza[6]helicene 、 四(3,5-二(三氟甲基)苯基)硼酸钠 在 盐酸 作用下， 以 乙醚 、 二氯甲烷 、 乙醇 为溶剂， 反应 2.0h， 以92%的产率得到(+)-(P)-11,12-benzo-2-(1-adamantylamino)-1-aza[6]helicenium TFPB
  参考文献：
  名称：

  Helical Chiral 2-Aminopyridinium Ions: A New Class of Hydrogen Bond Donor Catalysts

  摘要：

  Helical chiral 2-aminopyridinium ions were designed as a significantly more acidic (active) dual hydrogen-bonding catalyst than commonly used (thio)urea-based systems. The heticene framework was specifically utilized to position an inherently chiral barrier on the hydrogen-bonding side of the catalyst. The catalyst reactivity and enantioselectivity were successfully demonstrated in additions of 4,7-dihydroindoles to nitroalkenes (0.5-2 mol % catalyst loadings, up to 98:2 er).

  DOI：

  10.1021/ja100539c
• 作为产物：
  描述：

  (P)-11,12-benzo-1-aza[6]helicene N-oxide 、 金刚烷胺 在 4-甲苯磺酸酐 作用下， 以 二氯甲烷 为溶剂， 以95%的产率得到(+)-(P)-11,12-benzo-2-(1-adamantylamino)-1-aza[6]helicene
  参考文献：
  名称：

  Helical Chiral 2-Aminopyridinium Ions: A New Class of Hydrogen Bond Donor Catalysts

  摘要：

  Helical chiral 2-aminopyridinium ions were designed as a significantly more acidic (active) dual hydrogen-bonding catalyst than commonly used (thio)urea-based systems. The heticene framework was specifically utilized to position an inherently chiral barrier on the hydrogen-bonding side of the catalyst. The catalyst reactivity and enantioselectivity were successfully demonstrated in additions of 4,7-dihydroindoles to nitroalkenes (0.5-2 mol % catalyst loadings, up to 98:2 er).

  DOI：

  10.1021/ja100539c