3,5-bis-(5-hexylcarbamoyl-pentyloxy)-benzoic acid 10-azido-decyl ester | 1174917-35-1

• 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: 3,5-bis-(5-hexylcarbamoyl-pentyloxy)-benzoic acid 10-azido-decyl ester
• 英文别名: 10-Azidodecyl 3,5-bis[6-(hexylamino)-6-oxohexoxy]benzoate；10-azidodecyl 3,5-bis[6-(hexylamino)-6-oxohexoxy]benzoate
• CAS: 1174917-35-1
• 化学式: C₄₁H₇₁N₅O₆
• 分子量: 730.045
• InChiKey: WUWGARFJUMEDAX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.5
• 重原子数：
  52
• 可旋转键数：
  37
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  117
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1-十二炔 、 3,5-bis-(5-hexylcarbamoyl-pentyloxy)-benzoic acid 10-azido-decyl ester 在 copper(ll) sulfate pentahydrate 、 sodium ascorbate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 0.33h， 以50%的产率得到10-(4-decyl-3H-[1,2,3]triazol-1-yl)decyl 3,5-bis(5-hexylcarbamoylpentyloxy)benzoate
  参考文献：
  名称：

  Modification of self-assembled nanotubes by click chemistry generates new nanotubes by an out-of equilibrium process

  摘要：

  一种芳香族二酰胺化合物可在非极性溶剂中自组装形成直径为 27 纳米的纳米管。我们合成了这种化合物的不同类似物，发现带有炔基或叠氮基的类似物仍能形成直径相同的纳米管。这些官能团为直接在自组装管上进行铜催化炔和叠氮环加成反应（CuAACs）提供了可能性。冷冻断裂电子显微镜和 SAXS 显示，反应生成的新纳米管与初始纳米管的尺寸相似。对这些管子的化学分析表明，它们主要由反应分子组成。当这些新的纳米管受热解离时，它们无法从其组成分子中重新组装起来，这表明它们不是在平衡状态下传统的可逆自组装的结果。

  DOI：

  10.1039/c0sm00810a
• 作为产物：
  描述：

  3,5-bis-(5-hexylcarbamoylpentyloxy)-benzoic acid 10-methanesulfonyloxy-decyl ester 在 sodium azide 、 四丁基溴化铵 作用下， 以 丙酮 为溶剂， 反应 48.0h， 以100 mg的产率得到3,5-bis-(5-hexylcarbamoyl-pentyloxy)-benzoic acid 10-azido-decyl ester
  参考文献：
  名称：

  Direct functionalization of self-assembled nanotubes overcomes unfavorable self-assembling processes

  摘要：

  含有炔基和叠氮基的二酰胺在自组装成纳米管后，通过“点击化学”与其自组装状态下的低分子量分子反应；生成的化合物仍自组装成新的纳米管，这些纳米管无法通过构成分子的简单自组装形成。

  DOI：

  10.1039/b903797g

文献信息

• Formation of reactive aerogels and their reactivity in aqueous media. Wettability induces hydrophobic vs. hydrophilic selectivity
  作者：Thi-Thanh-Tam Nguyen、François-Xavier Simon、Niaz Ali Khan、Marc Schmutz、Philippe J. Mésini

  DOI：10.1039/c2jm30184a

  日期：——

  Aerogels were formed from organogels of diamides by a supercritical drying process. The used organogels are composed of self-assembled nanotubes of 29 nm in diameter. SEM studies reveal that the resulting aerogels are made of fibers with diameters comprised between 40 and 200 nm, corresponding to bundles of the starting nanotubes, while WAXS indicated that most of the crystalline structure detected in the self-assemblies of the starting gel is preserved in aerogels. Two different reactive diamides bearing respectively an alkynyl and an azido function were investigated. We have tested the reactivity of the resulting aerogels under copper-catalyzed azide–alkyne cycloaddition in aqueous solution. These aerogels react easily with hydrophobic compounds although reactants are in separate phases. In contrast, they do not react with hydrosoluble compounds, because of their superhydrophobicity.

  气凝胶是由二酰胺有机凝胶通过超临界干燥工艺形成的。使用的有机凝胶由直径为 29 纳米的自组装纳米管组成。扫描电子显微镜（SEM）研究表明，气凝胶由直径介于 40 纳米和 200 纳米之间的纤维组成，与起始纳米管束相对应，而 WAXS 表明，在起始凝胶的自组装中检测到的结晶结构大部分在气凝胶中得以保留。我们研究了两种不同的活性二酰胺，它们分别具有炔基和叠氮功能。我们在水溶液中测试了铜催化叠氮-炔环化反应下生成的气凝胶的反应性。尽管反应物处于不同的相中，但这些气凝胶很容易与疏水性化合物发生反应。相反，由于它们具有超疏水性，因此不会与水溶性化合物发生反应。
• Direct functionalization of self-assembled nanotubes overcomes unfavorable self-assembling processes
  作者：Thi-Thanh-Tam Nguyen、François-Xavier Simon、Marc Schmutz、Philippe J. Mésini

  DOI：10.1039/b903797g

  日期：——

  Diamides containing alkyne and azido were self-assembled into nanotubes and were reacted under their self-assembled state with small molecules by “click chemistry”; the resulting compounds remain self-assembled into new nanotubes that cannot be formed by simple self-assembly of the constituting molecules.

  含有炔基和叠氮基的二酰胺在自组装成纳米管后，通过“点击化学”与其自组装状态下的低分子量分子反应；生成的化合物仍自组装成新的纳米管，这些纳米管无法通过构成分子的简单自组装形成。
• Modification of self-assembled nanotubes by click chemistry generates new nanotubes by an out-of equilibrium process
  作者：Thi-Thanh-Tam Nguyen、François-Xavier Simon、Jérôme Combet、Marc Schmutz、Philippe J. Mésini

  DOI：10.1039/c0sm00810a

  日期：——

  An aromatic diamide compound self-assembles in non-polar solvents to form nanotubes with diameters of 27 nm. We have synthesized different analogues of this compound and we found that the ones bearing an alkyne or an azide group are still able to form nanotubes with diameters of the same order. The functional groups offered the possibility to perform copper catalyzed alkyne and azide cycloadditions (CuAACs), which were achieved directly on the self-assembled tubes. The reaction yielded new nanotubes with similar dimensions to the starting ones, as shown by freeze fracture electron microscopy and SAXS. Chemical analysis of those tubes shows that they are composed mainly of the reacted molecules. When these new nanotubes are dissociated by heat they cannot be re-assembled from their constituting molecules, which shows that they do not result from a conventional reversible self-assembly at equilibrium.

  一种芳香族二酰胺化合物可在非极性溶剂中自组装形成直径为 27 纳米的纳米管。我们合成了这种化合物的不同类似物，发现带有炔基或叠氮基的类似物仍能形成直径相同的纳米管。这些官能团为直接在自组装管上进行铜催化炔和叠氮环加成反应（CuAACs）提供了可能性。冷冻断裂电子显微镜和 SAXS 显示，反应生成的新纳米管与初始纳米管的尺寸相似。对这些管子的化学分析表明，它们主要由反应分子组成。当这些新的纳米管受热解离时，它们无法从其组成分子中重新组装起来，这表明它们不是在平衡状态下传统的可逆自组装的结果。