8,13-bis(5-chloro-8-hydroxyquinolin-7-ylmethyl)-3-hydroxymethyl-8,13-diaza-1,3,10-trithiacyclopentadecane

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 8,13-bis(5-chloro-8-hydroxyquinolin-7-ylmethyl)-3-hydroxymethyl-8,13-diaza-1,3,10-trithiacyclopentadecane
• 英文别名: 7,7'-[[2-(Hydroxymethyl)-1,4,10-trithia-7,13-diazacyclopentadecane-7,13-diyl]bis(methylene)]bis[5-chloro-8-quinolinol]；5-chloro-7-[[13-[(5-chloro-8-hydroxyquinolin-7-yl)methyl]-2-(hydroxymethyl)-1,4,10-trithia-7,13-diazacyclopentadec-7-yl]methyl]quinolin-8-ol
• 化学式: C₃₁H₃₆Cl₂N₄O₃S₃
• 分子量: 679.756
• InChiKey: UADAUPVGOMDPDN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  43
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  169
• 氢给体数：
  3
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  bis<2-(α-chloroacetamido)ethyl> sulfide 在 硼烷四氢呋喃络合物 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 乙腈 为溶剂， 反应 144.0h， 生成 8,13-bis(5-chloro-8-hydroxyquinolin-7-ylmethyl)-3-hydroxymethyl-8,13-diaza-1,3,10-trithiacyclopentadecane
  参考文献：
  名称：

  Bis-8-hydroxyquinoline-Armed Diazatrithia-15-crown-5 and Diazatrithia-16-crown-5 Ligands:  Possible Fluorophoric Metal Ion Sensors

  摘要：

  The synthesis and preliminary photophysical properties of a series of diazatrithia-15-crown-5 and diazatrithia-16-crown-5 ligands containing two 8-hydroxyquinoline sidearms are reported. The ligands were prepared by a two-step process. First, diazatrithiacrown ethers 11 and 12 were prepared by treating bis(alpha -chloroamide)5 with various dimercaptans followed by reduction using a boron-THF complex. Hydroxymethyl-substituted macrocycle 12 was rearranged to hydroxysubstituted diazatrithia-16-crown-5 in refluxing aqueous HCl. Macrocyclic diamines 11-13 were converted to either 5-chloro-8-hydroxyquinolin-7-ylmethyl-sudstituted diazatrithiacrown ethers 14-16 by a Mannich aminomethylation reaction or to 8-hydroxyquinolin-2-ylmethyl-substituted diazatrithiacrown ethers 17-19 by reductive amination using 8-hydroxyquinoline-2-carboxaldehyde. Preliminary photophysical studies show that ligands 16 and 19 exhibit increased fluorescence in the presence of Zn2+, indicating that these ligands could be chemical sensors for Zn2+.

  DOI：

  10.1021/jo0017584

文献信息

• Bis-8-hydroxyquinoline-Armed Diazatrithia-15-crown-5 and Diazatrithia-16-crown-5 Ligands:  Possible Fluorophoric Metal Ion Sensors
  作者：R. Todd Bronson、Jerald S. Bradshaw、Paul B. Savage、Saowarux Fuangswasdi、Sang Chul Lee、Krzysztof E. Krakowiak、Reed M. Izatt

  DOI：10.1021/jo0017584

  日期：2001.7.1

  The synthesis and preliminary photophysical properties of a series of diazatrithia-15-crown-5 and diazatrithia-16-crown-5 ligands containing two 8-hydroxyquinoline sidearms are reported. The ligands were prepared by a two-step process. First, diazatrithiacrown ethers 11 and 12 were prepared by treating bis(alpha -chloroamide)5 with various dimercaptans followed by reduction using a boron-THF complex. Hydroxymethyl-substituted macrocycle 12 was rearranged to hydroxysubstituted diazatrithia-16-crown-5 in refluxing aqueous HCl. Macrocyclic diamines 11-13 were converted to either 5-chloro-8-hydroxyquinolin-7-ylmethyl-sudstituted diazatrithiacrown ethers 14-16 by a Mannich aminomethylation reaction or to 8-hydroxyquinolin-2-ylmethyl-substituted diazatrithiacrown ethers 17-19 by reductive amination using 8-hydroxyquinoline-2-carboxaldehyde. Preliminary photophysical studies show that ligands 16 and 19 exhibit increased fluorescence in the presence of Zn2+, indicating that these ligands could be chemical sensors for Zn2+.