2-[[2-[2,3-bis[2-[[2-(dioctylamino)-2-oxoethyl]amino]-2-oxoethoxy]-5-(hydrazinecarbonyl)phenoxy]acetyl]amino]-N,N-dioctylacetamide | 1250403-93-0

• 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-[2,3-bis[2-[[2-(dioctylamino)-2-oxoethyl]amino]-2-oxoethoxy]-5-(hydrazinecarbonyl)phenoxy]acetyl]amino]-N,N-dioctylacetamide
• CAS: 1250403-93-0
• 化学式: C₆₇H₁₂₂N₈O₁₀
• 分子量: 1199.75
• InChiKey: CBJJRGUFJZTYHH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  17.5
• 重原子数：
  85
• 可旋转键数：
  58
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  231
• 氢给体数：
  5
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  2-[[2-[2,3-bis[2-[[2-(dioctylamino)-2-oxoethyl]amino]-2-oxoethoxy]-5-(hydrazinecarbonyl)phenoxy]acetyl]amino]-N,N-dioctylacetamide 、 对苯二甲醛 以 甲醇 为溶剂， 反应 12.0h， 以95%的产率得到
  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
• 作为产物：
  描述：

  methyl 3,4,5-tris(2-((2-(dioctylamino)-2-oxoethyl)amino)-2-oxoethoxy)benzoate 在 一水合肼 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 以66%的产率得到2-[[2-[2,3-bis[2-[[2-(dioctylamino)-2-oxoethyl]amino]-2-oxoethoxy]-5-(hydrazinecarbonyl)phenoxy]acetyl]amino]-N,N-dioctylacetamide
  参考文献：
  名称：

  p-Phenyleneethynylene-based comb-like oligomers: the synthesis and self-assembling property

  摘要：

  This paper describes the self-assembling property of three series of p-phenyleneethynylene based comb-like oligomers, which carry multiple peripheral side chains of different polarity. The new oligomers are prepared readily through the formation of the hydrazone bonds from the corresponding aldehyde and gallic acid-derived benzohydrazides. In polar solvents such as methanol and ethanol, the oligomers that bear n-decyl or 2-(2-(dioctylamino)-2-oxoethyl-amino)-2-oxoethoxyl unit (DOAOE) segments as the side chains are revealed to form vesicular structures, while the oligomers carrying hydrophilic oligo(ethyleneglycol) side chains do not. The structures of the vesicles are evidenced by SEM, AFM, TEM, and dye-encapsulation experiments. UV-vis absorption spectroscopic experiments suggest that the vesicles are generated through the stacking of the conjugated backbones, which is promoted by the solvophobic interaction of the peripheral side chains. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.01.082

文献信息

• p-Phenyleneethynylene-based comb-like oligomers: the synthesis and self-assembling property
  作者：Liu-Gang Wang、Tian-Guang Zhan、Xin Zhao、Xi-Kui Jiang、Zhan-Ting Li

  DOI：10.1016/j.tet.2012.01.082

  日期：2012.7

  This paper describes the self-assembling property of three series of p-phenyleneethynylene based comb-like oligomers, which carry multiple peripheral side chains of different polarity. The new oligomers are prepared readily through the formation of the hydrazone bonds from the corresponding aldehyde and gallic acid-derived benzohydrazides. In polar solvents such as methanol and ethanol, the oligomers that bear n-decyl or 2-(2-(dioctylamino)-2-oxoethyl-amino)-2-oxoethoxyl unit (DOAOE) segments as the side chains are revealed to form vesicular structures, while the oligomers carrying hydrophilic oligo(ethyleneglycol) side chains do not. The structures of the vesicles are evidenced by SEM, AFM, TEM, and dye-encapsulation experiments. UV-vis absorption spectroscopic experiments suggest that the vesicles are generated through the stacking of the conjugated backbones, which is promoted by the solvophobic interaction of the peripheral side chains. (C) 2012 Elsevier Ltd. All rights reserved.
• 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.