2-{3,5-bis-[(4-dodecyl-phenylcarbamoyl)-methyl]-2,4,6-trimethoxy-phenyl}-N-(4-dodecylphenyl)acetamide | 862896-38-6

• 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: 2-{3,5-bis-[(4-dodecyl-phenylcarbamoyl)-methyl]-2,4,6-trimethoxy-phenyl}-N-(4-dodecylphenyl)acetamide
• 英文别名: 2-[3,5-bis[2-(4-dodecylanilino)-2-oxoethyl]-2,4,6-trimethoxyphenyl]-N-(4-dodecylphenyl)acetamide
• CAS: 862896-38-6
• 化学式: C₆₉H₁₀₅N₃O₆
• 分子量: 1072.61
• InChiKey: HLMUSYOAWMVSEY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  22.8
• 重原子数：
  78
• 可旋转键数：
  45
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  115
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-{3,5-bis-[(4-dodecyl-phenylcarbamoyl)-methyl]-2,4,6-trimethoxy-phenyl}-N-(4-dodecylphenyl)acetamide 在 三溴化硼 作用下， 以 异丙醇 为溶剂， 生成 2-{5,7-bis[(4-dodecyl-phenylcarbamoyl)methyl]-4,6,10-trioxo-1-aza-tricyclo[3.3.1.1^3,7]dec-3-yl}-N-(4-dodecyl-phenyl)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：

  2,4,6-tricyanomethyl-1,3,5-trimethoxybenzene 在 sodium hydroxide 、 氯化亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 反应 12.0h， 生成 2-{3,5-bis-[(4-dodecyl-phenylcarbamoyl)-methyl]-2,4,6-trimethoxy-phenyl}-N-(4-dodecylphenyl)acetamide
  参考文献：
  名称：

  Enhanced Small-Molecule Assembly through Directional Intramolecular Forces

  摘要：

  Directional intramolecular interactions play a critical role in the self-assembly of donor-or-acceptor molecules in solution. Amide functions on the periphery of the tricyclic core stabilize a C-3-symmetric monomer conformation by intramolecular hydrogen bonding and dipole-dipole interactions. The molecules are effective organogelators and show long-range ordering in the bulk.

  DOI：

  10.1021/ol051768x

文献信息

• Rapid access to <i>C</i> ₃- and <i>C</i> _s-symmetric AAT organogelators via ring opening of a common benzotrifuranone precursor
  作者：Matthew B. Baker、Ling Yuan、Christopher J. Marth、Yan Li、Ronald K. Castellano

  DOI：10.1080/10610278.2010.500733

  日期：2010.11.1

  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.
• Enhanced Small-Molecule Assembly through Directional Intramolecular Forces
  作者：Andrew J. Lampkins、Osama Abdul-Rahim、Hengfeng Li、Ronald K. Castellano

  DOI：10.1021/ol051768x

  日期：2005.9.1

  Directional intramolecular interactions play a critical role in the self-assembly of donor-or-acceptor molecules in solution. Amide functions on the periphery of the tricyclic core stabilize a C-3-symmetric monomer conformation by intramolecular hydrogen bonding and dipole-dipole interactions. The molecules are effective organogelators and show long-range ordering in the bulk.