3,4-bis[(Z)-octadec-9-enoxy]benzoyl chloride | 926652-63-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3,4-bis[(Z)-octadec-9-enoxy]benzoyl chloride
• CAS: 926652-63-3
• 化学式: C₄₃H₇₃ClO₃
• 分子量: 673.504
• InChiKey: RJRGEEFYKOXSRV-CLFAGFIQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  18.4
• 重原子数：
  47
• 可旋转键数：
  35
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3,4-bis[(Z)-octadec-9-enoxy]benzoyl chloride 在 盐酸 、 sodium hydroxide 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 1.0h， 生成 N-{4-[4-(4-aminobutylamino)-butylamino]-butyl}-3,4-bis-octadec-9-enyloxy-benzamide trihydrochloride
  参考文献：
  名称：

  Synthesis and Transfection Efficiencies of New Lipophilic Polyamines

  摘要：

  A homologous series of lipophilic polyamines was synthesized and evaluated for DNA delivery and transfection efficiency. The series contained 1,4-butanediamine, 1,8-octanediamine, 2-[2-(2-amino-ethoxy)-ethoxy]-ethylamine, homospermidine, and homospermine covalently attached via their N-1 terminus to a 3,4-bis(oleyloxy)-benzyl motif. In addition, homospermidine and homospermine were also attached via amide linkers. The homospermidine derivatives (i.e., benzyl tether 25 and benzamide tether 27) showed a 3-fold and 4-fold respective enhancement in delivery of AlexaFluor-488-labeled DNA over the butanediamine analogue 22. Homospermine derivative 26 was shown to inhibit C-14-spermine uptake (IC50 similar to 10 mu M), which implied that 26 is able to compete effectively for polyamine recognition sites on the cell surface. This study demonstrated that the number and position of the positive charges along the polyamine scaffold plays a key role in DNA delivery and in determining the transfection efficiency.

  DOI：

  10.1021/jm0607101
• 作为产物：
  描述：

  1-溴-顺-9-十八碳烯 在 N,N-二甲基甲酰胺 氢氧化钾 、 草酰氯 、 potassium carbonate 、 potassium iodide 作用下， 以 乙醇 、 二氯甲烷 、 环己酮 、 苯 为溶剂， 反应 23.0h， 生成 3,4-bis[(Z)-octadec-9-enoxy]benzoyl chloride
  参考文献：
  名称：

  Synthesis and Transfection Efficiencies of New Lipophilic Polyamines

  摘要：

  A homologous series of lipophilic polyamines was synthesized and evaluated for DNA delivery and transfection efficiency. The series contained 1,4-butanediamine, 1,8-octanediamine, 2-[2-(2-amino-ethoxy)-ethoxy]-ethylamine, homospermidine, and homospermine covalently attached via their N-1 terminus to a 3,4-bis(oleyloxy)-benzyl motif. In addition, homospermidine and homospermine were also attached via amide linkers. The homospermidine derivatives (i.e., benzyl tether 25 and benzamide tether 27) showed a 3-fold and 4-fold respective enhancement in delivery of AlexaFluor-488-labeled DNA over the butanediamine analogue 22. Homospermine derivative 26 was shown to inhibit C-14-spermine uptake (IC50 similar to 10 mu M), which implied that 26 is able to compete effectively for polyamine recognition sites on the cell surface. This study demonstrated that the number and position of the positive charges along the polyamine scaffold plays a key role in DNA delivery and in determining the transfection efficiency.

  DOI：

  10.1021/jm0607101