1,4,10-三硫杂-7,13-二氮杂环十五碳n-2-基甲醇 | 122023-94-3

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 1,4,10-三硫杂-7,13-二氮杂环十五碳n-2-基甲醇
• 英文名称: 2-hydroxymethyl-7,14-diaza-1,4,10-trithiacyclopentadecane
• 英文别名: 1,4,10-Trithia-7,13-diazacyclopentadecane-2-methanol；1,4,10-trithia-7,13-diazacyclopentadec-2-ylmethanol
• CAS: 122023-94-3
• 化学式: C₁₁H₂₄N₂OS₃
• 分子量: 296.522
• InChiKey: OWGUDDFGUMSSOZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  120
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,4,10-三硫杂-7,13-二氮杂环十五碳n-2-基甲醇 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 28.0h， 生成 8,14-bis(5-chloro-8-hydroxyquinolin-7-ylmethyl)-3-hydroxy-8,14-diaza-1,5,11-trithiacyclohexadecane
  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
• 作为产物：
  描述：

  3-hydroxymethyl-7,13-diaza-1,4,10-trithiacyclopentadecane-6,14-dione 在 硼烷四氢呋喃络合物 、 盐酸 作用下， 以 四氢呋喃 为溶剂， 反应 72.0h， 以85%的产率得到1,4,10-三硫杂-7,13-二氮杂环十五碳n-2-基甲醇
  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

• A convenient synthesis and preliminary photophysical study of novel fluoroionophores: macrocyclic polyamines containing two dansylamidoethyl side arms
  作者：Guoping Xue、Jerald S Bradshaw、Huacan Song、R.Todd Bronson、Paul B Savage、Kryzsztof E Krakowiak、Reed M Izatt、Luca Prodi、Marco Montalti、Nelsi Zaccheroni

  DOI：10.1016/s0040-4020(00)00999-6

  日期：2001.1

  A series of novel fluorophores, consisting of macrocyclic polyamines containing two dansylamidoethyl side arms were synthesized as potential zinc (II) fluoroionophores by the reaction of the appropriate macrocyclic polyamines with N-dansylaziridine in acetonitrile at reflux temperature. Preliminary photophysical studies of ligand 3a, 1,7-dimethyl-4,10-bis(dansylamidoethyl)-1,4,7,10-tetraazacyclododecane, 3j, 8,13-bis(dansylamidoethyl)-3-hydroxymethyl-1,3,10-trithia-8-13-diazacyclopentadecane, and their complexes with Cu2+, Zn2+, Cd2+, and Hg2+ are described. (C) 2000 Elsevier Science Ltd. All rights reserved.
• 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+.