6,7,9,10,12,13,15,16-octahydro-22H-dibenzo[n,q][1,4,7,10,13,16]pentaoxazacyclooctadecine-22-carbaldehyde | 1006702-16-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6,7,9,10,12,13,15,16-octahydro-22H-dibenzo[n,q][1,4,7,10,13,16]pentaoxazacyclooctadecine-22-carbaldehyde
• CAS: 1006702-16-4
• 化学式: C₂₁H₂₅NO₆
• 分子量: 387.433
• InChiKey: BUVMXGMOAQPIQQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  28.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  66.46
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  6,7,9,10,12,13,15,16-octahydro-22H-dibenzo[n,q][1,4,7,10,13,16]pentaoxazacyclooctadecine-22-carbaldehyde 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 0.5h， 以100%的产率得到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
• 作为产物：
  描述：

  N,N-bis(2-hydroxyphenyl)formamide 、 四乙二醇二对甲苯磺酸酯 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 65.0h， 以52%的产率得到6,7,9,10,12,13,15,16-octahydro-22H-dibenzo[n,q][1,4,7,10,13,16]pentaoxazacyclooctadecine-22-carbaldehyde
  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