(7R,17R)-7,17-dimethyl-N-prop-2-enyl-6,9,12,15,18-pentaoxa-25-azatetracyclo[21.3.1.05,26.019,24]heptacosa-1(27),2,4,19,21,23,25-heptaene-27-carboxamide | 1006702-08-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: (7R,17R)-7,17-dimethyl-N-prop-2-enyl-6,9,12,15,18-pentaoxa-25-azatetracyclo[21.3.1.05,26.019,24]heptacosa-1(27),2,4,19,21,23,25-heptaene-27-carboxamide
• CAS: 1006702-08-4
• 化学式: C₂₇H₃₂N₂O₆
• 分子量: 480.561
• InChiKey: VLSIXUPJOLZAOK-RTBURBONSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  35
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  88.1
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  、 丙烯胺 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.08h， 以1.45 g的产率得到(7R,17R)-7,17-dimethyl-N-prop-2-enyl-6,9,12,15,18-pentaoxa-25-azatetracyclo[21.3.1.05,26.019,24]heptacosa-1(27),2,4,19,21,23,25-heptaene-27-carboxamide
  参考文献：
  名称：

  Preparation of a new chiral acridino-18-crown-6 ether-based stationary phase for enantioseparation of racemic protonated primary aralkyl amines

  摘要：

  Starting from commercially available and relatively cheap chemicals first enantiopure dimethyl-substituted monoaza-18-crown-6 ether (R,R)-21 containing a diphenylamine unit was prepared, which was then transformed to dimethyl-substituted acridino-18-crown-6 ligand (R,R)-19 having an N-allyl-carbamoyl linker by several steps. The terminal double bond of the latter made possible to attach (R,R)19 to gamma-mercaptopropyl-functionalized spherical HPLC quality silica gel obtaining a new chiral stationary phase (R,R)-CSP-37. Based on electronic circular dichroism (ECD) studies the N-allyl-carbamoyl group attached to the acridine ring of the chiral host (R,R)-19 does weaken exciton interaction between the host and guest molecules, but does not destroy the discriminating power of the chiral host. An HPLC column filled with (R,R)-CSP-37 was tested for the en anti oseparation of racemic 1-(1-naphthyl)- and 1-(2-naphthyl)ethylamine hydrogenperchlorates using isocratic conditions. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.09.056