(E)-4,4'-bis(diethylphosphonatemethyl)stilbene | 1237530-38-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (E)-4,4'-bis(diethylphosphonatemethyl)stilbene
• 英文别名: 4,4'-bis[(diethoxyphosphoryl)methyl]stilbene；1-(diethoxyphosphorylmethyl)-4-[(E)-2-[4-(diethoxyphosphorylmethyl)phenyl]ethenyl]benzene
• CAS: 1237530-38-9
• 化学式: C₂₄H₃₄O₆P₂
• 分子量: 480.478
• InChiKey: HIABETAGPZPFQN-MDZDMXLPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  32
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N,N-bis(6'-iodohexyl)-4-aminobenzaldehyde 、 (E)-4,4'-bis(diethylphosphonatemethyl)stilbene 在 sodium t-butanolate 作用下， 以 四氢呋喃 为溶剂， 以76%的产率得到4,4'-bis(4'-(N,N-bis(6''-iodohexyl)amino)styryl)stilbene
  参考文献：
  名称：

  Modification of the Optoelectronic Properties of Membranes via Insertion of Amphiphilic Phenylenevinylene Oligoelectrolytes

  摘要：

  We report on the modification of membranes by incorporation of phenylenevinylene oligoelectrolytes with the goal of tailoring their optical and electronic properties and their applications. A water-soluble distyrylstilbene oligoelectrolyte (DSSN+), capped at each end with nitrogen bound, terminally charged pendant groups, was synthesized. The photophysical and solvatochromatic properties of DSSN+ and the shorter distyrylbenzene analogue DSBN+ were probed and found to be useful for characterizing insertion into membranes based on phospholipid vesicle systems. A combination of UV/visible absorbance and photoluminescence spectroscopies, together with confocal microscopy, were employed to confirm membrane incorporation. Examination of the emission intensity profile in stationary multilamellar vesicles obtained with a polarized excitation source provides insight into the orientation of these chromophores within lipid bilayers and indicates that these molecules are highly ordered, such that the hydrophobic electronically delocalized region positions within the inner membrane with the long molecular axis perpendicular to the bilayer plane. Cyclic voltammetry experiments provide evidence that DSSN+ and DSBN+ facilitate transmembrane electron transport across lipid bilayers supported on glassy carbon electrodes. Additionally, the interaction with living microorganisms was probed. Fluorescence imaging indicates that DSSN+ and DSBN+ preferentially accumulate within cell membranes. Furthermore, notable increases in yeast microbial fuel cell performance were observed when employing DSSN+ as the electron transport mediator.

  DOI：

  10.1021/ja1016156
• 作为产物：
  描述：

  4-溴苄基亚磷酸二乙酯 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 potassium acetate 、 palladium diacetate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 生成 (E)-4,4'-bis(diethylphosphonatemethyl)stilbene
  参考文献：
  名称：

  苄基膦酸二乙酯作为潜在抗菌剂的合成与评价

  摘要：

  研究了苄基膦酸二乙酯衍生物苯环取代基对细胞毒活性的影响。基于开发的钯催化的乙烯基酯的α，β-高二芳基化方案获得有机膦酸盐。提出了通往 1,2-双(4-((二乙氧基磷酰基)甲基)苯基)乙酸乙酯的新合成途径，该途径显着提高了最终产物的总产率（从 1% 提高到 38%）。几种新合成的有机膦酸盐作为新的潜在抗菌药物在大肠杆菌模型上进行了测试细菌菌株（K12 和 R2-R3）。所有测试的化合物都显示出对 K12 和 R2 菌株的最高选择性和活性。使用 MIC 和 MBC 测试以及修饰细菌 DNA 后 Fpg 消化的初步细胞研究表明，与通常使用的抗生素（如环丙沙星、博来霉素和氯唑西林）相比，选定的膦酸苄酯衍生物可能具有更大的抗菌剂潜力。基于所使用的模型菌株，这些化合物对致病性大肠杆菌菌株具有高度特异性，并且可能在未来作为常用抗生素的新替代品进行，由于细菌对各种药物和抗生素的耐药性增加，这一点尤其重要。

  DOI：

  10.3390/molecules27206865

文献信息

• Coordination-Driven Hierarchical Organization of π-Conjugated Systems: From Molecular to Supramolecular π-Stacked Assemblies
  作者：Yishan Yao、Wenting Shen、Brigitte Nohra、Christophe Lescop、Régis Réau

  DOI：10.1002/chem.201000621

  日期：2010.6.25

  alternative geometries (linear, angular). Linkers that incorporate an internal pyridyne moiety can also be employed. X‐ray diffraction studies revealed that the metallocyclophanes based on linear linkers self‐organize into infinite π‐stacked columns in the solid state with intermolecular distances of about 3.6 Å. This approach, based on coordination‐driven self‐assembly, provides a novel and rational strategy

  由异位夹钳组装而成的U形，双金属，Cu I络合物与氰基封端的π共轭连接基的反应可以直接轻松地以高收率获得π堆叠的金属环烷。在这些组件中，π壁几乎面对面排列。这种合理的超分子合成的多功能性通过使用具有纳米级长度（最高27.7Å），不同化学组成的连接子（oligo（para-苯基亚乙烯基）的OPV，低聚（亚苯基），低聚（苯基亚乙炔基）和其他几何形状（线性，角形）。也可以使用掺入内部吡啶炔部分的接头。X射线衍射研究表明，基于线性连接子的金属环烷可自组织成固态的无限π堆积柱，其分子间距离约为3.6。这种基于协调驱动的自组装的方法为固态扩展π系统的堆叠提供了一种新颖而合理的策略。
• AGENTS FOR ENHANCED CHARGE TRANSPORT ACROSS MICROBIAL MEMBRANES
  申请人：BAZAN Guillermo C.

  公开号：US20120264649A1

  公开（公告）日：2012-10-18

  The invention provides molecules useful for enhancing charge transport across membranes, such as electron transport across membranes, and methods of using such molecules, for example in improving the performance of a microbial fuel cell or in staining microbes for observation. The amphiphilic molecule comprises a conjugated core with hydrophilic groups on either end. The amphiphilic molecule inserts into the membrane of a microbe and facilitates charge transfer across the membrane of the microbe.
• Modification of the Optoelectronic Properties of Membranes via Insertion of Amphiphilic Phenylenevinylene Oligoelectrolytes
  作者：Logan E. Garner、Juhyun Park、Scott M. Dyar、Arkadiusz Chworos、James J. Sumner、Guillermo C. Bazan

  DOI：10.1021/ja1016156

  日期：2010.7.28

  We report on the modification of membranes by incorporation of phenylenevinylene oligoelectrolytes with the goal of tailoring their optical and electronic properties and their applications. A water-soluble distyrylstilbene oligoelectrolyte (DSSN+), capped at each end with nitrogen bound, terminally charged pendant groups, was synthesized. The photophysical and solvatochromatic properties of DSSN+ and the shorter distyrylbenzene analogue DSBN+ were probed and found to be useful for characterizing insertion into membranes based on phospholipid vesicle systems. A combination of UV/visible absorbance and photoluminescence spectroscopies, together with confocal microscopy, were employed to confirm membrane incorporation. Examination of the emission intensity profile in stationary multilamellar vesicles obtained with a polarized excitation source provides insight into the orientation of these chromophores within lipid bilayers and indicates that these molecules are highly ordered, such that the hydrophobic electronically delocalized region positions within the inner membrane with the long molecular axis perpendicular to the bilayer plane. Cyclic voltammetry experiments provide evidence that DSSN+ and DSBN+ facilitate transmembrane electron transport across lipid bilayers supported on glassy carbon electrodes. Additionally, the interaction with living microorganisms was probed. Fluorescence imaging indicates that DSSN+ and DSBN+ preferentially accumulate within cell membranes. Furthermore, notable increases in yeast microbial fuel cell performance were observed when employing DSSN+ as the electron transport mediator.
• The Synthesis and Evaluation of Diethyl Benzylphosphonates as Potential Antimicrobial Agents
  作者：Anna Brodzka、Paweł Kowalczyk、Damian Trzepizur、Dominik Koszelewski、Karol Kramkowski、Mateusz Szymczak、Aleksandra Wypych、Rafał Lizut、Ryszard Ostaszewski

  DOI：10.3390/molecules27206865

  日期：——

  new potential antimicrobial drugs on model Escherichia coli bacterial strains (K12 and R2-R3). All tested compounds show the highest selectivity and activity against K12 and R2 strains. Preliminary cellular studies using MIC and MBC tests and digestion of Fpg after modification of bacterial DNA suggest that selected benzylphosphonate derivatives may have greater potential as antibacterial agents than

  研究了苄基膦酸二乙酯衍生物苯环取代基对细胞毒活性的影响。基于开发的钯催化的乙烯基酯的α，β-高二芳基化方案获得有机膦酸盐。提出了通往 1,2-双(4-((二乙氧基磷酰基)甲基)苯基)乙酸乙酯的新合成途径，该途径显着提高了最终产物的总产率（从 1% 提高到 38%）。几种新合成的有机膦酸盐作为新的潜在抗菌药物在大肠杆菌模型上进行了测试细菌菌株（K12 和 R2-R3）。所有测试的化合物都显示出对 K12 和 R2 菌株的最高选择性和活性。使用 MIC 和 MBC 测试以及修饰细菌 DNA 后 Fpg 消化的初步细胞研究表明，与通常使用的抗生素（如环丙沙星、博来霉素和氯唑西林）相比，选定的膦酸苄酯衍生物可能具有更大的抗菌剂潜力。基于所使用的模型菌株，这些化合物对致病性大肠杆菌菌株具有高度特异性，并且可能在未来作为常用抗生素的新替代品进行，由于细菌对各种药物和抗生素的耐药性增加，这一点尤其重要。