6,7,9,10,12,13,15,16-octahydro-22H-dibenzo[n,q][1,4,7,10,13,16]pentaoxazacyclooctadecine | 281680-52-2

• 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
• 英文别名: 9,12,15,18,21-Pentaoxa-2-azatricyclo[20.4.0.03,8]hexacosa-1(26),3,5,7,22,24-hexaene
• CAS: 281680-52-2
• 化学式: C₂₀H₂₅NO₅
• 分子量: 359.422
• InChiKey: HNOPZSTWTJWJAF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  26
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 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 、 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 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：

  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

文献信息

• Cyclic di[(o-polyethyleneglycoxy)phenyl]amine: new members in the crown ether family
  作者：Loı̈c J Charbonnière、Raymond F Ziessel

  DOI：10.1016/s0040-4039(00)00203-3

  日期：2000.4

  The synthesis of cyclic ethers based on polyethyleneglycol chains grafted on di(o-hydroxyphenyl)amine is described. The starting diarylamine is obtained from a melted salt procedure and coupled to the tosylated tri-, tetra- and pentaethyleneglycol. The X-ray crystal structure of the tetraethyleneglycol derivative was determined. For the triethyleneglycol compound, alkylation of the nitrogen atom with

  描述了基于接枝在二（邻-羟基苯基）胺上的聚乙二醇链的环醚的合成。起始二芳基胺是从熔融盐法获得的，并与甲苯磺酸化的三乙二醇，四乙二醇和五乙二醇偶联。测定了四乙二醇衍生物的X射线晶体结构。对于三甘醇化合物，氮原子与5-溴甲基-5'-甲基-2,2'-联吡啶（过量或1当量）的烷基化分别导致季铵盐或叔胺衍生物。后者与[Re（CO）5 Cl]反应，以面部构型得到相应的Re（I）络合物。