(4-{10-[10-(4-Methoxycarbonylmethoxy-benzyloxycarbonylamino)-decyldisulfanyl]-decylcarbamoyloxymethyl}-phenoxy)-acetic acid methyl ester | 551772-78-2

• 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: (4-{10-[10-(4-Methoxycarbonylmethoxy-benzyloxycarbonylamino)-decyldisulfanyl]-decylcarbamoyloxymethyl}-phenoxy)-acetic acid methyl ester
• CAS: 551772-78-2
• 化学式: C₄₂H₆₄N₂O₁₀S₂
• 分子量: 821.11
• InChiKey: KWERIEOFLNSZBC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.57
• 重原子数：
  56.0
• 可旋转键数：
  33.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  147.72
• 氢给体数：
  2.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  (4-{10-[10-(4-Methoxycarbonylmethoxy-benzyloxycarbonylamino)-decyldisulfanyl]-decylcarbamoyloxymethyl}-phenoxy)-acetic acid methyl ester 在 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 48.0h， 以86%的产率得到(4-{10-[10-(4-Carboxymethoxy-benzyloxycarbonylamino)-decyldisulfanyl]-decylcarbamoyloxymethyl}-phenoxy)-acetic acid
  参考文献：
  名称：

  Surfaces Designed for Charge Reversal

  摘要：

  We have created surfaces which switch from cationic at pH < 3 to anionic at pH > 5, by attaching aminodicarboxylic acid units to silica and gold substrates. Charge reversal was demonstrated by monitoring the adsorption of cationic dyes (methylene blue and a tetracationic porphyrin) and an anionic sulfonated porphyrin, at a range of pH using UV-vis absorption and reflection spectroscopy. The cationic dyes bind under neutral conditions (pH 5-7) and are released at pH 1-4, whereas the anionic dye binds under acidic conditions (pH 1-4) and is released at pH 5-7. Gold surfaces were functionalized with two different amphoteric disulfides with short (CH2)(2) and long (CH2)(10)CONH(CH2)(6) linkers; the longer disulfide gave surfaces exhibiting charge reversal in a narrower pH range. Adsorption is much faster on the functionalized gold (t(1/2) = 62 s) than on functionalized silica (t(1/2) = 6900 s), but the final extents of coverage on both surface are similar, for a given dye at a given pH, with maximal coverages of around 2 molecules nm(-2). These charge-reversal processes are reversible and can be repeatedly cycled by changing the pH. We have also created surfaces which undergo irreversible proton-triggered charge switching, using a carbamate-linked thiol carboxylic acid which cleaves in acid. These surfaces are versatile new tools for controlling electrostatic self-assembly at surfaces.

  DOI：

  10.1021/ja028338b
• 作为产物：
  描述：

  双(10-羧癸基)二硫化物 在 二苯基膦叠氮化物 、 1,8-双二甲氨基萘 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 22.0h， 生成 (4-{10-[10-(4-Methoxycarbonylmethoxy-benzyloxycarbonylamino)-decyldisulfanyl]-decylcarbamoyloxymethyl}-phenoxy)-acetic acid methyl ester
  参考文献：
  名称：

  Surfaces Designed for Charge Reversal

  摘要：

  We have created surfaces which switch from cationic at pH < 3 to anionic at pH > 5, by attaching aminodicarboxylic acid units to silica and gold substrates. Charge reversal was demonstrated by monitoring the adsorption of cationic dyes (methylene blue and a tetracationic porphyrin) and an anionic sulfonated porphyrin, at a range of pH using UV-vis absorption and reflection spectroscopy. The cationic dyes bind under neutral conditions (pH 5-7) and are released at pH 1-4, whereas the anionic dye binds under acidic conditions (pH 1-4) and is released at pH 5-7. Gold surfaces were functionalized with two different amphoteric disulfides with short (CH2)(2) and long (CH2)(10)CONH(CH2)(6) linkers; the longer disulfide gave surfaces exhibiting charge reversal in a narrower pH range. Adsorption is much faster on the functionalized gold (t(1/2) = 62 s) than on functionalized silica (t(1/2) = 6900 s), but the final extents of coverage on both surface are similar, for a given dye at a given pH, with maximal coverages of around 2 molecules nm(-2). These charge-reversal processes are reversible and can be repeatedly cycled by changing the pH. We have also created surfaces which undergo irreversible proton-triggered charge switching, using a carbamate-linked thiol carboxylic acid which cleaves in acid. These surfaces are versatile new tools for controlling electrostatic self-assembly at surfaces.

  DOI：

  10.1021/ja028338b