5-(5,5-dimethyl-1,3-dioxolane-2-yl)-17-formyl-25,26,27,28-tetra(2-ethoxyethoxy)calix[4]arene | 211040-64-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-(5,5-dimethyl-1,3-dioxolane-2-yl)-17-formyl-25,26,27,28-tetra(2-ethoxyethoxy)calix[4]arene
• 英文别名: 17-(5,5-Dimethyl-1,3-dioxan-2-yl)-25,26,27,28-tetrakis(2-ethoxyethoxy)pentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(25),3,5,7(28),9(27),10,12,15(26),16,18,21,23-dodecaene-5-carbaldehyde
• CAS: 211040-64-1
• 化学式: C₅₁H₆₆O₁₁
• 分子量: 855.078
• InChiKey: NTMOSQMBAFSHQN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.5
• 重原子数：
  62
• 可旋转键数：
  22
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.51
• 拓扑面积：
  109
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  5-(5,5-dimethyl-1,3-dioxolane-2-yl)-17-formyl-25,26,27,28-tetra(2-ethoxyethoxy)calix[4]arene 在 palladium on activated charcoal 氢气 、 三乙胺 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 48.0h， 生成
  参考文献：
  名称：

  Novel Water-Soluble β-Cyclodextrin−Calix[4]arene Couples as Fluorescent Sensor Molecules for the Detection of Neutral Analytes

  摘要：

  The synthesis and the host-guest chemistry of two novel fluorescent beta-cyclodextrin-calix[4]arene couples 1 and 2 is described. The compounds were prepared by coupling a beta-cyclodextrin linked with an aminoxylyl spacer with two different calix[4]arene building blocks each bearing a fluorophore. The fluorophores attached to 1 and 2 are the 2-naphthylamine and the dansyl moiety, respectively. The unsymmetric calix[4]arene functionalization was achieved by monoprotection of the 1,3-diformylcalix[4]arene. The host molecules 1 and 2 were used as fluorescent probes for several organic analytes in aqueous solution. 1 shows sensitivity for a series of neutral organic guest species, such as steroids, terpenes, and other natural products. In contrast, compound 2 does not show sensitivity for organic analytes in aqueous solution. The different behavior of the two fluorescent probes 1 and 2 is explained by the different strength of self-inclusion of each fluorphoric group into the beta-cyclodextrin cavity.

  DOI：

  10.1021/jo9723321
• 作为产物：
  描述：

  5,17-diformyl-25,26,27,28-tetrakis(2-ethoxyethoxy)calix<4>arene 、 2,2-二甲基-1,3-丙二醇 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以56%的产率得到5-(5,5-dimethyl-1,3-dioxolane-2-yl)-17-formyl-25,26,27,28-tetra(2-ethoxyethoxy)calix[4]arene
  参考文献：
  名称：

  Novel Water-Soluble β-Cyclodextrin−Calix[4]arene Couples as Fluorescent Sensor Molecules for the Detection of Neutral Analytes

  摘要：

  The synthesis and the host-guest chemistry of two novel fluorescent beta-cyclodextrin-calix[4]arene couples 1 and 2 is described. The compounds were prepared by coupling a beta-cyclodextrin linked with an aminoxylyl spacer with two different calix[4]arene building blocks each bearing a fluorophore. The fluorophores attached to 1 and 2 are the 2-naphthylamine and the dansyl moiety, respectively. The unsymmetric calix[4]arene functionalization was achieved by monoprotection of the 1,3-diformylcalix[4]arene. The host molecules 1 and 2 were used as fluorescent probes for several organic analytes in aqueous solution. 1 shows sensitivity for a series of neutral organic guest species, such as steroids, terpenes, and other natural products. In contrast, compound 2 does not show sensitivity for organic analytes in aqueous solution. The different behavior of the two fluorescent probes 1 and 2 is explained by the different strength of self-inclusion of each fluorphoric group into the beta-cyclodextrin cavity.

  DOI：

  10.1021/jo9723321