2-[[2-[5-[2-[[2-(dioctylamino)-2-oxoethyl]amino]-2-oxoethoxy]-2,4-bis(hydrazinecarbonyl)phenoxy]acetyl]amino]-N,N-dioctylacetamide | 1031691-52-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-[[2-[5-[2-[[2-(dioctylamino)-2-oxoethyl]amino]-2-oxoethoxy]-2,4-bis(hydrazinecarbonyl)phenoxy]acetyl]amino]-N,N-dioctylacetamide
• CAS: 1031691-52-7
• 化学式: C₄₈H₈₆N₈O₈
• 分子量: 903.26
• InChiKey: QLUJQUDMFIERHE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.3
• 重原子数：
  64
• 可旋转键数：
  40
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  228
• 氢给体数：
  6
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2-[[2-[5-[2-[[2-(dioctylamino)-2-oxoethyl]amino]-2-oxoethoxy]-2,4-bis(hydrazinecarbonyl)phenoxy]acetyl]amino]-N,N-dioctylacetamide 、 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以74%的产率得到
  参考文献：
  名称：

  Vesicles and Organogels from Foldamers: A Solvent-Modulated Self-Assembling Process

  摘要：

  Nonamphiphilic, hydrogen-bonded hydrazide foldamers appended with four or six long flexible chains were revealed to spontaneously assemble to form vesicles in methanol and organogels in aliphatic hydrocarbons. SEM, AFM, TEM, DLS, and fluorescence microscopy were all used to identify the structures of the vesicles. It was proposed that intermolecular pi stacking of the folded frameworks and hydrogen bonding of the amide units in the appended chains induced the molecules to produce cylindrical aggregates. In polar methanol, these aggregates packed together to generate one-layered vesicles owing to hydrophobically induced entanglement of the peripheral chains, while in nonpolar hydrocarbons, the peripheral chains entwined across stacked cylinders to form three-dimensional networks and thus immobilize the liquid molecules.

  DOI：

  10.1021/ja801618p
• 作为产物：
  描述：

  Dimethyl 4,6-bis[2-[[2-(dioctylamino)-2-oxoethyl]amino]-2-oxoethoxy]benzene-1,3-dicarboxylate 在 肼 作用下， 以 甲醇 为溶剂， 反应 6.0h， 以70%的产率得到2-[[2-[5-[2-[[2-(dioctylamino)-2-oxoethyl]amino]-2-oxoethoxy]-2,4-bis(hydrazinecarbonyl)phenoxy]acetyl]amino]-N,N-dioctylacetamide
  参考文献：
  名称：

  Hydrogen-bonded benzylidenebenzohydrazide macrocycles and oligomers: testing the robust capacity of an amide chain in promoting the formation of vesicles

  摘要：

  This Letter describes 2-(2-(dioctylamino)-2-oxoethyl-amino)-2-oxoethoxyl (DPAOE)-tuned self-assembly of vesicles from rigid macrocycles and foldamer-like oligomers. The molecules are prepared through the formation of reversible hydrazone bonds from aldehyde and benzo-hydrazide precursors, which are further facilitated by intramolecular N center dot center dot center dot H-O hydrogen bonding. SEM. AFM, and fluorescent encapsulation studies reveal that the molecules all self-assemble into vesicular structures in methanol, while similar molecules bearing the triethylene glycol or n-decyl chains do not. The results illustrate that DOAOE is robust in promoting the formation of vesicles for aromatic Systems in polar solvents. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.05.076

文献信息

• Vesicles and Organogels from Foldamers: A Solvent-Modulated Self-Assembling Process
  作者：Wei Cai、Gui-Tao Wang、Yun-Xiang Xu、Xi-Kui Jiang、Zhan-Ting Li

  DOI：10.1021/ja801618p

  日期：2008.6.1

  Nonamphiphilic, hydrogen-bonded hydrazide foldamers appended with four or six long flexible chains were revealed to spontaneously assemble to form vesicles in methanol and organogels in aliphatic hydrocarbons. SEM, AFM, TEM, DLS, and fluorescence microscopy were all used to identify the structures of the vesicles. It was proposed that intermolecular pi stacking of the folded frameworks and hydrogen bonding of the amide units in the appended chains induced the molecules to produce cylindrical aggregates. In polar methanol, these aggregates packed together to generate one-layered vesicles owing to hydrophobically induced entanglement of the peripheral chains, while in nonpolar hydrocarbons, the peripheral chains entwined across stacked cylinders to form three-dimensional networks and thus immobilize the liquid molecules.
• Hydrogen-bonded benzylidenebenzohydrazide macrocycles and oligomers: testing the robust capacity of an amide chain in promoting the formation of vesicles
  作者：Ben-Ye Lu、Guang-Jun Sun、Jian-Bin Lin、Xi-Kui Jiang、Xin Zhao、Zhan-Ting Li

  DOI：10.1016/j.tetlet.2010.05.076

  日期：2010.7

  This Letter describes 2-(2-(dioctylamino)-2-oxoethyl-amino)-2-oxoethoxyl (DPAOE)-tuned self-assembly of vesicles from rigid macrocycles and foldamer-like oligomers. The molecules are prepared through the formation of reversible hydrazone bonds from aldehyde and benzo-hydrazide precursors, which are further facilitated by intramolecular N center dot center dot center dot H-O hydrogen bonding. SEM. AFM, and fluorescent encapsulation studies reveal that the molecules all self-assemble into vesicular structures in methanol, while similar molecules bearing the triethylene glycol or n-decyl chains do not. The results illustrate that DOAOE is robust in promoting the formation of vesicles for aromatic Systems in polar solvents. (C) 2010 Elsevier Ltd. All rights reserved.