2,2',2''-(2,4,6-trihydroxybenzene-1,3,5-triyl)tris(N-(naphthalen-2-yl)acetamide) | 1333164-80-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2,2',2''-(2,4,6-trihydroxybenzene-1,3,5-triyl)tris(N-(naphthalen-2-yl)acetamide)
• CAS: 1333164-80-9
• 化学式: C₄₂H₃₃N₃O₆
• 分子量: 675.741
• InChiKey: ZLAXDHKSFHQLBH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.81
• 重原子数：
  51.0
• 可旋转键数：
  9.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  147.99
• 氢给体数：
  6.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  乌洛托品 、 2,2',2''-(2,4,6-trihydroxybenzene-1,3,5-triyl)tris(N-(naphthalen-2-yl)acetamide) 以 异丙醇 为溶剂， 反应 120.0h， 以66%的产率得到2,2',2''-(4,6,10-trioxo-1-azaadamantane-3,5,7-triyl)tris(N-(naphthalen-2-yl)acetamide)
  参考文献：
  名称：

  Rapid access to C ₃- and C _s-symmetric AAT organogelators via ring opening of a common benzotrifuranone precursor

  摘要：

  Presented is a rapid and general approach to functionalised 1-aza-adamantanetrione (AAT) donor-sigma-acceptor molecules from a phloroglucinol-derived trilactone, benzotrifuranone (BTF). Ten C3-symmetric AATs bearing diverse aryl amide substituents are accessed in two synthetic steps: (1) the exhaustive ring opening of BTF with aromatic amine nucleophiles (performed in up to 91% yield) and (2) cyclisation with hexamethylenetetramine (performed in up to 75% yield). Additionally, stepwise ring opening of BTF allows synthesis of phloroglucinol intermediates with two unique aryl amide substituents and ultimately Cs-symmetric AATs. Of the novel AATs prepared, three (including the Cs-symmetric hybrid) are effective gelators of chlorinated solvents (critical gelation concentration (CGC)=0.2-0.4 wt%) and one, with naphthyl substituents, forms translucent gels from aromatic solvents (CGC0.3 wt%). The combination of AATs with moderately electron-poor and electron-rich aromatic substituents results in functional complementarity and gelation at concentrations below what is required for the individual components. Electron microscopy of the gel morphologies shows high aspect ratio fibres underlying the gel network superstructures in most cases. Polarised optical microscopy has allowed imaging of representative native organogel phases, and reveals striking morphology differences between gels that also share different optical and/or thermal stability properties.

  DOI：

  10.1080/10610278.2010.500733
• 作为产物：
  描述：

  benzotrifuranone 、 2-萘胺 以 N,N-二甲基甲酰胺 为溶剂， 以55%的产率得到2,2',2''-(2,4,6-trihydroxybenzene-1,3,5-triyl)tris(N-(naphthalen-2-yl)acetamide)
  参考文献：
  名称：

  Rapid access to C ₃- and C _s-symmetric AAT organogelators via ring opening of a common benzotrifuranone precursor

  摘要：

  Presented is a rapid and general approach to functionalised 1-aza-adamantanetrione (AAT) donor-sigma-acceptor molecules from a phloroglucinol-derived trilactone, benzotrifuranone (BTF). Ten C3-symmetric AATs bearing diverse aryl amide substituents are accessed in two synthetic steps: (1) the exhaustive ring opening of BTF with aromatic amine nucleophiles (performed in up to 91% yield) and (2) cyclisation with hexamethylenetetramine (performed in up to 75% yield). Additionally, stepwise ring opening of BTF allows synthesis of phloroglucinol intermediates with two unique aryl amide substituents and ultimately Cs-symmetric AATs. Of the novel AATs prepared, three (including the Cs-symmetric hybrid) are effective gelators of chlorinated solvents (critical gelation concentration (CGC)=0.2-0.4 wt%) and one, with naphthyl substituents, forms translucent gels from aromatic solvents (CGC0.3 wt%). The combination of AATs with moderately electron-poor and electron-rich aromatic substituents results in functional complementarity and gelation at concentrations below what is required for the individual components. Electron microscopy of the gel morphologies shows high aspect ratio fibres underlying the gel network superstructures in most cases. Polarised optical microscopy has allowed imaging of representative native organogel phases, and reveals striking morphology differences between gels that also share different optical and/or thermal stability properties.

  DOI：

  10.1080/10610278.2010.500733