methyl 3,5-bis{[3,5-bis(2-propynyloxy)benzyl]oxy}benzoate | 1123207-37-3

• 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: methyl 3,5-bis{[3,5-bis(2-propynyloxy)benzyl]oxy}benzoate
• 英文别名: methyl 3,5-Bis[3,5-bis(propargyloxy)benzyloxy]benzoate
• CAS: 1123207-37-3
• 化学式: C₃₄H₂₈O₈
• 分子量: 564.592
• InChiKey: GTCYYVDPVCYOHU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.68
• 重原子数：
  42.0
• 可旋转键数：
  15.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  81.68
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  methyl 3,5-bis{[3,5-bis(2-propynyloxy)benzyl]oxy}benzoate 在 lithium aluminium tetrahydride 、 三溴化磷 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.5h， 生成 5,5'-(((5-(bromomethyl)-1,3-phenylene)bis(oxy))bis(methylene))bis(1,3-bis(prop-2-yn-1-yloxy)benzene)
  参考文献：
  名称：

  Effects of Dendron Generation and Salt Concentration on Phase Structures of Dendritic–Linear Block Copolymers with a Semirigid Dendron Containing PEG Tails

  摘要：

  We prepared a series of dendritic linear block copolymers (DLBCPs) bearing a semirigid Percec-type dendron with ionophilic poly(ethylene glycol) (PEG) tails and a polystyrene (PS) linear polymer by nitroxide-mediated living radical polymerization (NMRP). As the DLBCPs are connected by an ester linkage, through hydrolysis the molecular weights of the DLBCPs were precisely characterized by gel permeation chromatography and MALDI-TOF MS. Differential scanning calorimetry, small-angle X-ray scattering, and transmission electron microscopy were used to investigate the phase behaviors of the DLBCPs. Results show that the PEG tails of the semirigid dendron display a cold crystallization peak and a melting peak during the second heating process, while for the neat DLBCPs, the crystallization of the PEG tails is completely inhibited, and only the glass transition temperature (T-g) of the PS block is observed. However, T-g of the dendron block can be observed by complexing the DLBCPs with LiCF3SO3, suggesting that microphase separation occurs in the doped DLBCPs. Comparing the phase behaviors of the DLBCPs having the same dendron weight fraction (w(D) = 0.14) with varying dendron generation and salt concentration, we found that the G(1) or G(2) DLBCP undergoes a phase transition from a hexagonally packed cylinder structure to a lamellar structure with increasing content of LiCF3SO3. However, the G(3) DLBCP only displays a lamellar phase, and the lamellar thickness increases with increasing salt concentration. The difference can be attributed to the different degree of chain branching, which leads to different interface curvature.

  DOI：

  10.1021/ma300654j
• 作为产物：
  描述：

  3,5-dipropargyloxybenzyl alcohol 在 18-冠醚-6 、 三溴化磷 、 potassium carbonate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 26.5h， 生成 methyl 3,5-bis{[3,5-bis(2-propynyloxy)benzyl]oxy}benzoate
  参考文献：
  名称：

  Effects of Dendron Generation and Salt Concentration on Phase Structures of Dendritic–Linear Block Copolymers with a Semirigid Dendron Containing PEG Tails

  摘要：

  We prepared a series of dendritic linear block copolymers (DLBCPs) bearing a semirigid Percec-type dendron with ionophilic poly(ethylene glycol) (PEG) tails and a polystyrene (PS) linear polymer by nitroxide-mediated living radical polymerization (NMRP). As the DLBCPs are connected by an ester linkage, through hydrolysis the molecular weights of the DLBCPs were precisely characterized by gel permeation chromatography and MALDI-TOF MS. Differential scanning calorimetry, small-angle X-ray scattering, and transmission electron microscopy were used to investigate the phase behaviors of the DLBCPs. Results show that the PEG tails of the semirigid dendron display a cold crystallization peak and a melting peak during the second heating process, while for the neat DLBCPs, the crystallization of the PEG tails is completely inhibited, and only the glass transition temperature (T-g) of the PS block is observed. However, T-g of the dendron block can be observed by complexing the DLBCPs with LiCF3SO3, suggesting that microphase separation occurs in the doped DLBCPs. Comparing the phase behaviors of the DLBCPs having the same dendron weight fraction (w(D) = 0.14) with varying dendron generation and salt concentration, we found that the G(1) or G(2) DLBCP undergoes a phase transition from a hexagonally packed cylinder structure to a lamellar structure with increasing content of LiCF3SO3. However, the G(3) DLBCP only displays a lamellar phase, and the lamellar thickness increases with increasing salt concentration. The difference can be attributed to the different degree of chain branching, which leads to different interface curvature.

  DOI：

  10.1021/ma300654j

文献信息

• Efficient Synthesis of Muramic and Glucuronic Acid Glycodendrimers as Dengue Virus Antagonists
  作者：Cecilia García‐Oliva、Alfredo H. Cabanillas、Almudena Perona、Pilar Hoyos、Ángel Rumbero、María J. Hernáiz

  DOI：10.1002/chem.201903788

  日期：2020.2.3

  interactions, thus increasing their binding strengths to proteins. In this work, we report the efficient synthesis of novel muramic and glucuronic acid glycodendrimers as potential Dengue virus antagonists. Aromatic scaffolds functionalized with a terminal ethynyl groups were coupled to muramic and glucuronic acid azides by click chemistry through optimized synthetic strategies to afford the desired glycodendrimers

  碳水化合物通过糖-蛋白相互作用参与许多重要的病理过程，例如细菌和病毒感染。具有多种碳水化合物的糖缀合物参与多价相互作用，因此增加了它们与蛋白质的结合强度。在这项工作中，我们报告了新型的山武和葡萄糖醛酸糖树状聚合物作为潜在的登革热病毒拮抗剂的有效合成。通过点击化学，通过优化的合成策略，通过点击化学将具有末端乙炔基官能化的芳族支架偶联至村族和葡糖醛酸叠氮化物，从而以高收率提供所需的糖类树状聚合物。表面等离子体共振研究表明，所报道的化合物与登革热病毒包膜蛋白有效结合。进行了分子建模研究以模拟和解释观察到的结合。这些研究证实，可以轻松地实现糖类树状聚合物的有效化学合成，从而为寻找针对登革热病毒的新活性化合物提供了一种通用的策略。
• Direct Enzymatic Branch-End Extension of Glycocluster-Presented Glycans: An Effective Strategy for Programming Glycan Bioactivity
  作者：Carlos Bayón、Ning He、Mario Deir-Kaspar、Pilar Blasco、Sabine André、Hans-Joachim Gabius、Ángel Rumbero、Jesús Jiménez-Barbero、Wolf-Dieter Fessner、María J. Hernáiz

  DOI：10.1002/chem.201604550

  日期：2017.1.31

  based on N‐acetyl/glycolyl‐neuraminic acid incorporation. We assess the ensuing effect on their bioactivity for a plant toxin, and present an analysis of the noncovalent substrate binding contacts that the added sialic acid moiety makes to the lectin. Enzymatic diversification of a scaffold‐presented glycan can thus be brought to completion in situ, offering a versatile perspective for rational glycocluster

  聚糖的序列及其呈递的拓扑结构决定了糖受体（凝集素）识别的特异性和选择性。如果可以在保持所有其他参数不变的情况下有效地原位修饰糖簇的聚糖部分，则将进一步进行结构活性分析。通过使用细菌α2,6-唾液酸转移酶和一个小的二价至四价糖簇文库，我们说明了支架表达的乳糖苷单元已完全转化为基于N的两个不同的唾液酸化配体-乙酰基/羟乙酸神经氨酸结合。我们评估其对植物毒素的生物活性的随之而来的影响，并提出对添加唾液酸部分使凝集素产生非共价底物结合接触的分析。因此，可以在原位完成支架提供的聚糖的酶促多样化，从而为合理的糖簇工程设计提供了多方面的视角。
• Pyrene-Excimers-Based Antenna Systems
  作者：Stefano Cicchi、Pierangelo Fabbrizzi、Giacomo Ghini、Alberto Brandi、Paolo Foggi、Agnese Marcelli、Roberto Righini、Chiara Botta

  DOI：10.1002/chem.200801379

  日期：2009.1.5

  AbstractA series of dendrimeric compounds bearing pyrene units were synthesized to afford light‐harvesting antennae based on the formation of intramolecular excimers. The synthetic plan profited from the efficiency of the Huisgen reaction, the 1,3‐dipolar cycloaddition of azides and terminal alkynes, which allowed ready assembly of the different building blocks. The three molecular antennae obtained, of increasing generation, revealed efficient energy transfer both in solution and in the solid state.
• Design and sustainable synthesis of small mannose-based glycodendrons as ligands for HIV-1 envelope protein gp120: Toward an explanation for their binding
  作者：Carlos Martínez、Alejandro Merchán、Almudena Perona、Pedro Ramírez-López、José Ramón Suárez、María J. Hernáiz

  DOI：10.1016/j.cattod.2023.114493

  日期：2024.3