(6R,16R)-6,16-dimethyl-6,7,9,10,12,13,15,16-octahydro-22H-dibenzo[n,q][1,4,7,10,13,16]pentaoxazacyclooctadecine | 1006702-18-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (6R,16R)-6,16-dimethyl-6,7,9,10,12,13,15,16-octahydro-22H-dibenzo[n,q][1,4,7,10,13,16]pentaoxazacyclooctadecine
• 英文别名: (10R,20R)-10,20-dimethyl-9,12,15,18,21-pentaoxa-2-azatricyclo[20.4.0.03,8]hexacosa-1(26),3,5,7,22,24-hexaene
• CAS: 1006702-18-6
• 化学式: C₂₂H₂₉NO₅
• 分子量: 387.476
• InChiKey: KUEIMIRUBNQJIJ-QZTJIDSGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  28
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  58.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  草酰氯 、 (6R,16R)-6,16-dimethyl-6,7,9,10,12,13,15,16-octahydro-22H-dibenzo[n,q][1,4,7,10,13,16]pentaoxazacyclooctadecine 以 甲苯 为溶剂， 反应 1.17h， 生成 (6R,16R)-6,16-dimethyl-6,7,9,10,12,13,15,16-octahydro-22H-dibenzo[n,q][1,4,7,10,13,16]pentaoxazacyclooctadecin-22-yl(oxo)acetyl chloride
  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
• 作为产物：
  描述：

  (6R,16R)-6,16-dimethyl-6,7,9,10,12,13,15,16-octahydro-22H-dibenzo[n,q][1,4,7,10,13,16]pentaoxazacyclooctadecine-22-carbaldehyde 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 10.0h， 以88%的产率得到(6R,16R)-6,16-dimethyl-6,7,9,10,12,13,15,16-octahydro-22H-dibenzo[n,q][1,4,7,10,13,16]pentaoxazacyclooctadecine
  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

文献信息

• Preparation of a new chiral acridino-18-crown-6 ether-based stationary phase for enantioseparation of racemic protonated primary aralkyl amines
  作者：Szilvia Lakatos、József Fetter、Ferenc Bertha、Péter Huszthy、Tünde Tóth、Viktor Farkas、György Orosz、Miklós Hollósi

  DOI：10.1016/j.tet.2007.09.056

  日期：2008.2

  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.