5-formyl-17-(2'-naphthylaminomethyl)-25,26,27,28-tetra(2-ethoxyethoxy)calix[4]arene | 211040-62-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5-formyl-17-(2'-naphthylaminomethyl)-25,26,27,28-tetra(2-ethoxyethoxy)calix[4]arene
• 英文别名: 25,26,27,28-Tetrakis(2-ethoxyethoxy)-17-[(naphthalen-2-ylamino)methyl]pentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(24),3,5,7(28),9,11,13(27),15(26),16,18,21(25),22-dodecaene-5-carbaldehyde
• CAS: 211040-62-9
• 化学式: C₅₆H₆₅NO₉
• 分子量: 896.133
• InChiKey: GNXKWHJGNIIONC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.6
• 重原子数：
  66
• 可旋转键数：
  24
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  103
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  mono(2^A-O-{α-[4-(aminomethyl)tolyl]})hexakis(2^B,2^C,2^D,2^E,2^F,2^G-O-methyl)heptakis(6-O-tert-butyldimethylsilyl)-β-cyclodextrin 、 5-formyl-17-(2'-naphthylaminomethyl)-25,26,27,28-tetra(2-ethoxyethoxy)calix[4]arene 在 sodium cyanoborohydride 、 溶剂黄146 作用下， 生成 (1S,3R,5R,6S,8R,10R,11S,13R,15R,16S,18R,20R,21S,23R,25R,26S,28R,30R,31S,33R,35R,36S,37R,38S,39R,40S,41R,42S,43R,44S,45R,46S,47R,48S,49R)-5,10,15,20,25,30,35-heptakis[[tert-butyl(dimethyl)silyl]oxymethyl]-37,39,41,43,47,49-hexamethoxy-45-[[4-[[[25,26,27,28-tetrakis(2-ethoxyethoxy)-17-[(naphthalen-2-ylamino)methyl]-5-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-dodecaenyl]methylamino]methyl]phenyl]methoxy]-2,4,7,9,12,14,17,19,22,24,27,29,32,34-tetradecaoxaoctacyclo[31.2.2.23,6.28,11.213,16.218,21.223,26.228,31]nonatetracontane-36,38,40,42,44,46,48-heptol
  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 在 盐酸 、 sodium cyanoborohydride 、 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 72.5h， 生成 5-formyl-17-(2'-naphthylaminomethyl)-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

文献信息

• Novel Water-Soluble β-Cyclodextrin−Calix[4]arene Couples as Fluorescent Sensor Molecules for the Detection of Neutral Analytes
  作者：Jürgen Bügler、Johan F. J. Engbersen、David N. Reinhoudt

  DOI：10.1021/jo9723321

  日期：1998.8.1

  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.