N-(3-iodopropyl)-N,N-dioctyl-1-octanammonium iodide | 141438-07-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-(3-iodopropyl)-N,N-dioctyl-1-octanammonium iodide
• 英文别名: N-(3-iodopropyl)-N,N-dioctyl-1-octanaminium iodide；3-iodopropyl(trioctyl)azanium;iodide
• CAS: 141438-07-5
• 化学式: C₂₇H₅₇IN*I
• 分子量: 649.565
• InChiKey: CUYLIGOSJSCLLH-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  6.71
• 重原子数：
  30.0
• 可旋转键数：
  24.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  N-(3-iodopropyl)-N,N-dioctyl-1-octanammonium iodide 以 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 16.0h， 生成 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 、 1,3-二碘丙烷 以 乙醇 为溶剂， 反应 14.0h， 以56%的产率得到N-(3-iodopropyl)-N,N-dioctyl-1-octanammonium iodide
  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

文献信息

• Carriers for nucleotide 5'-triphosphate. 2. Liquid membrane and liposome transport
  作者：Tingyu Li、Sally J. Krasne、Bengt Persson、H. Ronald Kaback、Francois Diederich

  DOI：10.1021/jo00054a021

  日期：1993.1

  We describe a series of new cationic carriers for the transport of nucleotide 5'-triphosphates across liquid organic membranes. The tetracationic compound 5, with two diquaternary 1,4-diaza[2.2.2]bicyclooctane (DABCO) units, forms carrier-nucleotide complexes of 1:1 stoichiometry in dichloromethane and strongly accelerates nucleotide transport across this solvent. As a result of a favorable balance of hydrophobicity and hydrophilicity, complexes of 5 do not leak out of the organic phase into the aqueous source or receiving phases. Liposome transport studies demonstrate that caution is strongly advised when extrapolating from liquid membrane studies to the transport across liposomes or cell membranes. The DABCO-based cationic carriers do not mediate specific nucleotide transport across the liposome walls but rather act as detergents to break the liposomal structure.