3,3'-[oxybis(3,1-propanediyldiimino)]bis(4-ethoxy-3-cyclobutene-1,2-dione)

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 3,3'-[oxybis(3,1-propanediyldiimino)]bis(4-ethoxy-3-cyclobutene-1,2-dione)
• 英文别名: 3-Ethoxy-4-[3-[3-[(2-ethoxy-3,4-dioxocyclobuten-1-yl)amino]propoxy]propylamino]cyclobut-3-ene-1,2-dione；3-ethoxy-4-[3-[3-[(2-ethoxy-3,4-dioxocyclobuten-1-yl)amino]propoxy]propylamino]cyclobut-3-ene-1,2-dione
• 化学式: C₁₈H₂₄N₂O₇
• 分子量: 380.398
• InChiKey: FZBAPNBMNWQZAY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  27
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  120
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  氨基丙基醚 、 3,3'-[oxybis(3,1-propanediyldiimino)]bis(4-ethoxy-3-cyclobutene-1,2-dione) 以 乙醇 为溶剂， 反应 7.0h， 以94%的产率得到6,19-dioxa-2,10,15,23-tetraazatricyclo[22.2.0.0^11,14]hexacosa-1(24),11(14)-diene-12,13,25,26-tetraone
  参考文献：
  名称：

  Conformational Preferences and Self-Template Macrocyclization of Squaramide-Based Foldable Modules

  摘要：

  Secondary squaramides have considerable potential as hydrogen bond donors and acceptors. In CHCl3 both, anti- and syn-squaramide rotamers are observed by NMR. The energetic barrier for anti/syn mutual interconversion determined by complete band shape analysis is similar to63 kJ mol(-1). As in proline derivatives, a low rotational barrier is crucial for the design of foldable modules. In this paper, folding based on the low rotational barrier of squaramides is driven by donor atoms (N or O) located in the gamma position of an alkyl chain of a secondary squaramide. We demonstrate that the resulting minimal module exists as a folded conformer through the formation of a nine-membered ring stabilized by intramolecular hydrogen bonding. Molecular mechanics calculations and NMR studies support the existence of these folded conformers. The intramolecularly hydrogen bonded conformers are clearly visible even in CHCl3-EtOH mixtures. Folding occurs even in pure ethanol. As an indirect test, we studied the effectiveness of macrocyclization reactions in pure ethanol that require an effective templating effect to take place. The high yields obtained support the dominant role of a folded conformer even in this solvent.

  DOI：

  10.1021/jo035546t
• 作为产物：
  描述：

  氨基丙基醚 、 方酸二乙酯 以 乙醚 为溶剂， 反应 12.0h， 以97%的产率得到3,3'-[oxybis(3,1-propanediyldiimino)]bis(4-ethoxy-3-cyclobutene-1,2-dione)
  参考文献：
  名称：

  Conformational Preferences and Self-Template Macrocyclization of Squaramide-Based Foldable Modules

  摘要：

  Secondary squaramides have considerable potential as hydrogen bond donors and acceptors. In CHCl3 both, anti- and syn-squaramide rotamers are observed by NMR. The energetic barrier for anti/syn mutual interconversion determined by complete band shape analysis is similar to63 kJ mol(-1). As in proline derivatives, a low rotational barrier is crucial for the design of foldable modules. In this paper, folding based on the low rotational barrier of squaramides is driven by donor atoms (N or O) located in the gamma position of an alkyl chain of a secondary squaramide. We demonstrate that the resulting minimal module exists as a folded conformer through the formation of a nine-membered ring stabilized by intramolecular hydrogen bonding. Molecular mechanics calculations and NMR studies support the existence of these folded conformers. The intramolecularly hydrogen bonded conformers are clearly visible even in CHCl3-EtOH mixtures. Folding occurs even in pure ethanol. As an indirect test, we studied the effectiveness of macrocyclization reactions in pure ethanol that require an effective templating effect to take place. The high yields obtained support the dominant role of a folded conformer even in this solvent.

  DOI：

  10.1021/jo035546t

文献信息

• Conformational Preferences and Self-Template Macrocyclization of Squaramide-Based Foldable Modules
  作者：M. Carmen Rotger、M. Neus Piña、Antonio Frontera、Gabriel Martorell、Pablo Ballester、Pere M. Deyà、Antoni Costa

  DOI：10.1021/jo035546t

  日期：2004.4.1

  Secondary squaramides have considerable potential as hydrogen bond donors and acceptors. In CHCl3 both, anti- and syn-squaramide rotamers are observed by NMR. The energetic barrier for anti/syn mutual interconversion determined by complete band shape analysis is similar to63 kJ mol(-1). As in proline derivatives, a low rotational barrier is crucial for the design of foldable modules. In this paper, folding based on the low rotational barrier of squaramides is driven by donor atoms (N or O) located in the gamma position of an alkyl chain of a secondary squaramide. We demonstrate that the resulting minimal module exists as a folded conformer through the formation of a nine-membered ring stabilized by intramolecular hydrogen bonding. Molecular mechanics calculations and NMR studies support the existence of these folded conformers. The intramolecularly hydrogen bonded conformers are clearly visible even in CHCl3-EtOH mixtures. Folding occurs even in pure ethanol. As an indirect test, we studied the effectiveness of macrocyclization reactions in pure ethanol that require an effective templating effect to take place. The high yields obtained support the dominant role of a folded conformer even in this solvent.