4,6-bis-{2-[2-(2-methoxy-ethoxy)-ethoxy]-ethoxy}-isophthalic acid monomethyl ester | 874210-38-5

• 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: 4,6-bis-{2-[2-(2-methoxy-ethoxy)-ethoxy]-ethoxy}-isophthalic acid monomethyl ester
• 英文别名: 5-Methoxycarbonyl-2,4-bis[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]benzoic acid；5-methoxycarbonyl-2,4-bis[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]benzoic acid
• CAS: 874210-38-5
• 化学式: C₂₃H₃₆O₁₂
• 分子量: 504.532
• InChiKey: CWRLNQGJBRDGED-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  35
• 可旋转键数：
  23
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  137
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  4,6-bis-{2-[2-(2-methoxy-ethoxy)-ethoxy]-ethoxy}-isophthalic acid monomethyl ester 在 草酰氯 作用下， 以 二氯甲烷 为溶剂， 生成 methyl 5-(chlorocarbonyl)-2,4-bis(2-(2-(2-methoxyethoxy)ethoxy)ethoxy)benzoate
  参考文献：
  名称：

  Improving the Efficiency of Forming ‘Unfavorable’ Products: Eight-Residue Macrocycles from Folded Aromatic Oligoamide Precursors

  摘要：

  基于芳香族低聚酰胺前体的环化，合成了由八个元连接苯残基组成的低聚酰胺大环，这些前体的折叠骨架通过三中心氢键刚性化。使用 EDCI/HOBt 作为偶联试剂，以五元二胺和三元二酸缩合为基础的另一条路线提供了环状八聚体，收率为 75%。

  DOI：

  10.1055/s-0029-1217173
• 作为产物：
  描述：

  对甲苯磺酸三缩乙二醇单甲醚酯 在 sodium hydroxide 、 potassium carbonate 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 4,6-bis-{2-[2-(2-methoxy-ethoxy)-ethoxy]-ethoxy}-isophthalic acid monomethyl ester
  参考文献：
  名称：

  通过整合氢键和动态共价相互作用在水介质中的序列特异性关联

  摘要：

  在非极性溶剂中以序列特异性方式关联成氢键双链体的寡酰胺链在水性介质中转化为二硫化物交联双链体。因此，通过将三苯甲基保护的硫醇基团（其允许二硫键的可逆形成）结合到寡酰胺链中，在水溶液和甲醇中仅形成由互补氢键序列组成的双链体。寡酰胺链的序列特异性交联通过 MALDI-TOF、反相 HPLC 和分离交联双链体得到证实。该研究表明，通过氢键和可逆共价相互作用的相互作用，多重氢键系统的序列特异性特征可以扩展到竞争介质中，

  DOI：

  10.1021/ja064515n

文献信息

• Synthesis of Crescent Aromatic Oligoamides
  作者：Lihua Yuan、Adam R. Sanford、Wen Feng、Aimin Zhang、Jin Zhu、Huaqiang Zeng、Kazuhiro Yamato、Minfeng Li、Joseph S. Ferguson、Bing Gong

  DOI：10.1021/jo050798a

  日期：2005.12.1

  This article describes the synthetic procedures for the preparation of crescent (and helical) aromatic oligoamides developed in recent years in our laboratory. The large-scale preparation of a variety of monomers derived from various tetrasubstituted benzenes is presented. Three different strategies for constructing various oligomers consisting of meta- and meta/para-linked benzene residues are discussed

  本文介绍了近年来在我们实验室中开发的新月形（和螺旋形）芳香族寡酰胺的合成方法。提出了衍生自各种四取代苯的各种单体的大规模制备。讨论了构建由间位和间位/对位连接的苯残基组成的各种低聚物的三种不同策略。分析了影响耦合效率和产量的因素。发达的合成方法为更长的低聚物的制备和固相合成的发展提供了基础。
• 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.
• The self-assembly of six-petal microflowers by hydrogen-bonded shape-persistent triangular aromatic hydrazide derivatives
  作者：Jian-Bin Lin、Gui-Tao Wang、Xi-Kui Jiang、Zhan-Ting Li

  DOI：10.1016/j.tetlet.2010.06.021

  日期：2010.8

  Six-petal microflowers have been self-assembled in methanol from C(3)-symmetric shape-persistent triangular aromatic hydrazide derivatives. Nine intramolecular hydrogen bonds are used to enhance the planarity of the aromatic backbone, while six 2-(2-(2-methoxyethoxy)ethoxy)-ethoxyl groups are appended to the rigid aromatic backbone. Scanning electron microscopy (SEM) images show that the molecules form unique six-petal flower-like aggregates in methanol. A self-assembling mechanism that is similar to the formation of snowflakes has been proposed. (C) 2010 Elsevier Ltd. All rights reserved.
• Sequence-Specific Association in Aqueous Media by Integrating Hydrogen Bonding and Dynamic Covalent Interactions
  作者：Minfeng Li、Kazuhiro Yamato、Joseph S. Ferguson、Bing Gong

  DOI：10.1021/ja064515n

  日期：2006.10.1

  in nonpolar solvents were converted into disulfide cross-linked duplexes in aqueous media. Thus, by incorporating trityl-protected thiol groups, which allows the reversible formation of disulfide bonds, into the oligoamide strands, only duplexes consisting of complementary hydrogen-bonding sequences were formed in aqueous solution as well as in methanol. The sequence-specific cross-linking of oligoamide

  在非极性溶剂中以序列特异性方式关联成氢键双链体的寡酰胺链在水性介质中转化为二硫化物交联双链体。因此，通过将三苯甲基保护的硫醇基团（其允许二硫键的可逆形成）结合到寡酰胺链中，在水溶液和甲醇中仅形成由互补氢键序列组成的双链体。寡酰胺链的序列特异性交联通过 MALDI-TOF、反相 HPLC 和分离交联双链体得到证实。该研究表明，通过氢键和可逆共价相互作用的相互作用，多重氢键系统的序列特异性特征可以扩展到竞争介质中，
• Improving the Efficiency of Forming ‘Unfavorable’ Products: Eight-Residue Macrocycles from Folded Aromatic Oligoamide Precursors
  作者：Wen Feng、Bing Gong、Shuliang Zou、Youzhou He、Yongan Yang、Yi Zhao、Lihua Yuan、Kazuhiro Yamato

  DOI：10.1055/s-0029-1217173

  日期：——

  Oligoamide macrocycles consisting of eight meta-linked benzene residues were synthesized based on the cyclization of aromatic oligoamide precursors having folded backbones rigidified by three-center hydrogen bonds. An alternative route based on the condensation of pentadimeric diamine and trimeric diacid provided the cyclic octamer in 75% yield using EDCI/HOBt as the coupling reagent.

  基于芳香族低聚酰胺前体的环化，合成了由八个元连接苯残基组成的低聚酰胺大环，这些前体的折叠骨架通过三中心氢键刚性化。使用 EDCI/HOBt 作为偶联试剂，以五元二胺和三元二酸缩合为基础的另一条路线提供了环状八聚体，收率为 75%。