1-<3-(trioctylammonio)propyl>-4-aza-1-azoniabicyclo<2.2.2>octane diiodide | 141438-08-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 1-<3-(trioctylammonio)propyl>-4-aza-1-azoniabicyclo<2.2.2>octane diiodide
• 英文别名: 1-[3-(trioctylammonio)propyl]-4-aza-1-azoniabicyclo[2.2.2]octane diiodide
• CAS: 141438-08-6
• 化学式: C₃₃H₆₉N₃*2I
• 分子量: 761.74
• InChiKey: GCKDYTRTARAKBH-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  5.42
• 重原子数：
  37.0
• 可旋转键数：
  25.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  3.24
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  1-iodo-N,N-dioctylacetamide 、 1-<3-(trioctylammonio)propyl>-4-aza-1-azoniabicyclo<2.2.2>octane diiodide 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以92%的产率得到1-<2-(dioctylamino)-2-oxoethyl>-4-<3-(trioctylammonio)propyl>-1,4-diazoniabicyclo<2.2.2>octane tribromide
  参考文献：
  名称：

  Carriers for liquid membrane transport of nucleotide 5'-triphosphates

  摘要：

  The transport of the nucleotide triphosphates adenosine 5'-triphosphate (ATP), cytidine 5'-triphosphate (CTP), 2',3'-dideoxythymidine 5'-triphosphate (ddTTP), and 3'-azido-2'-deoxythymidine 5'-triphosphate (AZTTP) across a liquid organic membrane mediated by cationic DABCO-derived carriers was studied. With their branched aliphatic chains, these compounds, which bear two (2), three (3), or four (4) quaternary ammonium centers show excellent solubility in chloroform, the solvent chosen as liquid organic membrane. The bisquaternary mono(DABCO) derivative 2 was found to be the most efficient carrier for all nucleotides. Concentration-dependent extraction studies showed that 2 undergoes formation of a 2:1 carrier-nucleotide complex in the chloroform phase. This stoichiometry differs from the 1:1 stoichiometry previously suggested by Tabushi et al. for the association between nucleotide 5'-triphosphates and a bisquaternary DABCO derivative. The tricationic compound 3 is generally inferior to 2 in its carrier properties but shows an unexpectedly high selectivity for transporting ddTTP. The tetracationic bis(DABCO) derivative 4 shows poor carrier properties since it forms highly water-soluble associations which prefer distribution into the aqueous phase rather than into the liquid membrane.

  DOI：

  10.1021/jo00038a039
• 作为产物：
  描述：

  三辛胺 以 乙醇 、 丙酮 为溶剂， 反应 28.0h， 生成 1-<3-(trioctylammonio)propyl>-4-aza-1-azoniabicyclo<2.2.2>octane diiodide
  参考文献：
  名称：

  Carriers for liquid membrane transport of nucleotide 5'-triphosphates

  摘要：

  The transport of the nucleotide triphosphates adenosine 5'-triphosphate (ATP), cytidine 5'-triphosphate (CTP), 2',3'-dideoxythymidine 5'-triphosphate (ddTTP), and 3'-azido-2'-deoxythymidine 5'-triphosphate (AZTTP) across a liquid organic membrane mediated by cationic DABCO-derived carriers was studied. With their branched aliphatic chains, these compounds, which bear two (2), three (3), or four (4) quaternary ammonium centers show excellent solubility in chloroform, the solvent chosen as liquid organic membrane. The bisquaternary mono(DABCO) derivative 2 was found to be the most efficient carrier for all nucleotides. Concentration-dependent extraction studies showed that 2 undergoes formation of a 2:1 carrier-nucleotide complex in the chloroform phase. This stoichiometry differs from the 1:1 stoichiometry previously suggested by Tabushi et al. for the association between nucleotide 5'-triphosphates and a bisquaternary DABCO derivative. The tricationic compound 3 is generally inferior to 2 in its carrier properties but shows an unexpectedly high selectivity for transporting ddTTP. The tetracationic bis(DABCO) derivative 4 shows poor carrier properties since it forms highly water-soluble associations which prefer distribution into the aqueous phase rather than into the liquid membrane.

  DOI：

  10.1021/jo00038a039