malonic acid bis(2-(2-(2-methoxyethoxy)ethoxy)ethyl ester | 173201-34-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: malonic acid bis(2-(2-(2-methoxyethoxy)ethoxy)ethyl ester
• 英文别名: di(3,6,9-trioxadecyl) malonate；Bis[2-[2-(2-methoxyethoxy)ethoxy]ethyl] propanedioate
• CAS: 173201-34-8
• 化学式: C₁₇H₃₂O₁₀
• 分子量: 396.435
• InChiKey: MMXOMVCEMZEOKT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  27
• 可旋转键数：
  22
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  108
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2,6-二氯甲基吡啶 、 malonic acid bis(2-(2-(2-methoxyethoxy)ethoxy)ethyl ester 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 Bis[2-[2-(2-methoxyethoxy)ethoxy]ethyl] 2-[[6-[3-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]-2-[2-[2-(2-methoxyethoxy)ethoxy]ethoxycarbonyl]-3-oxopropyl]pyridin-2-yl]methyl]propanedioate
  参考文献：
  名称：

  Palladium(II)-induced Alkali Metal Ion Incorporation of 2,6-Disubstituted Pyridines with Bis(alkoxyethyl) Malonate Subunits

  摘要：

  制备了一系列 2,6-双（2,2′-二烷氧基乙基）吡啶配体。其中几个配体通过反式-钯-Cl2 单元连接，可将碱金属离子从水介质萃取到氯仿介质中，而单个吡啶配体则不能作为萃取试剂。

  DOI：

  10.1246/cl.1999.1231
• 作为产物：
  描述：

  三甘醇单甲醚 、 丙二酸 在 N,N'-二环己基碳二亚胺 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 4.5h， 以97%的产率得到malonic acid bis(2-(2-(2-methoxyethoxy)ethoxy)ethyl ester
  参考文献：
  名称：

  新型富勒烯双加合物衍生物的合成及水溶性

  摘要：

  报道了四类 C60 的双加合物衍生物的合成。新化合物在水性溶剂中的溶解度得到提高，是富勒烯衍生物有史以来报道的最高水平之一。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)

  DOI：

  10.1002/ejoc.200300494

文献信息

• Water solubility, antioxidant activity and cytochrome C binding of four families of exohedral adducts of C60 and C70
  作者：Patrick Witte、Florian Beuerle、Uwe Hartnagel、Russell Lebovitz、Anastasia Savouchkina、Sevda Sali、Dirk Guldi、Nikos Chronakis、Andreas Hirsch

  DOI：10.1039/b711912g

  日期：——

  fullerenes of similar overall structure. Among the higher adducts, anionic derivatives have a higher antioxidant activity than comparable cationic compounds. To achieve sufficient water solubility without the aid of a surfactant or co-solvent at least three charges on the addends are required. Significantly, anionic in contrast to cationic fullerene adducts bind with high affinity to cytochrome C.

  在过去的十年中，许多不同的研究人员表明，经表面修饰的水溶性富勒烯在体外对活性氧（ROS）表现出强大的抗氧化活性，并在体内保护细胞和组织免受氧化损伤和细胞死亡。然而，开发富勒烯作为真正的候选药物的进展受到三个发展问题的阻碍：1）缺乏可扩展合成的方法；2）无法生产与药物应用兼容的高度纯化的单一物种区域异构体；和3）对于各种表面修饰（例如，阴离子对阳离子对电荷中性极性）对结构-功能关系的理解不足。为了应对这些挑战，我们已经设计并合成了十多种新型水溶性富勒烯，它们可以作为单一异构体进行纯化，我们相信可以以合理的成本进行规模生产。这些化合物的添加方式，亲脂性以及电荷的数量和类型不同，并检查了它们的水溶性，对超氧阴离子的抗氧化活性和细胞色素C的结合。我们的结果表明，树状水溶性富勒烯[60]单加合物表现出最高程度的与三羟甲基磺酸盐衍生的阴离子富勒烯以及总体结构相似的阳离子富勒烯相比，其抗超氧阴离子的体外
• Rigidified tetrathiafulvalene–[60]fullerene assemblies: towards the control of through-space orientation between both electroactive units
  作者：David Kreher、Michel Cariou、Sheng-Gao Liu、Eric Levillain、Jaume Veciana、Concepció Rovira、Alain Gorgues、Piétrick Hudhomme

  DOI：10.1039/b201695h

  日期：2002.6.21

  Our recent works on fused TTF–C60 dyads, (TTF)n–C60 polyads and C60–TTF–C60 dumbbell triads in which the acceptor C60 is doubly tethered to the donor tetrathiafulvalene through a rigidified cyclohexene ring are presented. This approach was developed in order to control the relative orientation as well as the distance between both donor and acceptor entities. Thereby, through-space interactions which are of great importance for photoinduced electron- and/or energy-transfer processes are expected to dominate because of the special topology of the molecules. The two linked C60 and TTF chromophores in such adducts are not only in close proximity but also have optimal orbital orientations, thus facilitating these through-space electronic interactions. These new C60-based assemblies were synthesized by [4 + 2] Diels–Alder cycloaddition reactions. The different methodologies considered for their synthesis are discussed, their analytical, spectroscopic characterizations and electrochemical properties are also described. The selective electro-oxidation or reduction afforded the corresponding radical cation and radical anion which were characterized by EPR. These C60-based assemblies were studied for their nonlinear optical and optical limiting applications. Moreover, intramolecular photoinduced charge-separation and charge-recombination processes in a fused C60–TTF–C60 dumbbell triad which was designed to be soluble in organic solvents were investigated by time-resolved absorption and fluorescence techniques. Appreciable interaction between the C60 moiety and TTF moiety in the ground state was suggested by steady-state absorption spectra and the fluorescence spectra showed considerable interaction in the singlet excited state. The nanosecond transient absorption spectra displayed the formation of the charge-separated radical pair C60–TTF˙+–C60˙−, characterized by a lifetime of ca. 20 ns in benzonitrile.

  我们最近的研究工作集中在融合的TTF–C60二聚体、(TTF)n–C60多聚体和C60–TTF–C60哑铃三聚体，这些体系中受体C60通过刚性的环己烯环与供体四硫富瓦烯双重连接。此方法的开发旨在控制供体和受体之间的相对方向和距离。因此，由于分子的特殊拓扑结构，空间内的相互作用在光诱导电子及/或能量转移过程中预计将占主导地位。这种加合物中连接的C60和TTF色团不仅相互接近，而且具有最佳的轨道取向，从而促进这些跨空间的电子相互作用。这些新的基于C60的组装体是通过[4 + 2]迪尔斯－阿尔德环加成反应合成的。文中讨论了其合成过程中考虑的不同方法，并描述了它们的分析、光谱特性及电化学性质。选择性电氧化或还原生成了相应的自由基阳离子和自由基阴离子，这些都通过电子顺磁共振（EPR）进行了表征。这些基于C60的组装体也被研究用于其非线性光学和光限制应用。此外，设计为可溶于有机溶剂的融合C60–TTF–C60哑铃三聚体中的分子内光诱导电荷分离和电荷重组过程通过时间分辨吸收和荧光技术进行了研究。在基态中，稳态吸收光谱表明C60基团与TTF基团之间存在显著的相互作用，而荧光光谱则显示在单重激发态中也存在较强的相互作用。纳秒瞬态吸收光谱显示了电荷分离的自由基对C60–TTF˙+–C60˙–，其在苯腈中表征的寿命约为20纳秒。
• Photoinduced electron transfer processes of a fused C₆₀–TTF–C₆₀dumbbell triad
  作者：David Kreher、Piétrick Hudhomme、Alain Gorgues、Hongxia Luo、Yasuyuki Araki、Osamu Ito

  DOI：10.1039/b303544c

  日期：——

  Intramolecular photoinduced charge-separation and charge-recombination processes in a fused C60–TTF–C60 dumbbell triad molecule, which has been designed to be soluble in organic solvents thanks to the substitution of C60 with polyalcoxy ester groups, have been investigated in various solvents by time-resolved absorption and fluorescence techniques. Appreciable interaction between the C60-moiety and

  融合 C60-TTF-C60 哑铃三元组分子中的分子内光诱导电荷分离和电荷复合过程，由于 C60 被聚烷氧基酯基团取代，该分子被设计为可溶于有机溶剂，已通过以下方法在各种溶剂中进行了研究时间分辨吸收和荧光技术。稳态吸收光谱表明基态 C60 部分和 TTF 部分之间存在明显的相互作用。荧光光谱表明在单重激发态也有相当大的相互作用。观察到 C60–TTF–C60 在甲苯、THF 和苯甲腈中的荧光寿命比甲富勒烯短，这表明电荷分离是通过 C60 部分的单重激发态发生的，产生离子对（C60–TTF˙ +–C60˙–), 皮秒瞬态吸收光谱证实了这一点。1000 nm处的纳秒瞬态吸收光谱表明C60-TTF˙+-C60˙-的形成，其在苯甲腈中以20 ns的寿命衰减为上限。在四氢呋喃和甲苯中，在约纳秒激光脉冲内没有观察到清晰的 C60-TTF˙+-C60˙- 瞬态吸收带。6 ns 持续时间，表明 C60–TTF˙+–C60˙−
• Synthesis and Anti-HIV properties of new water-soluble bis-functionalized[60]fullerene derivatives
  作者：Susanna Bosi、Tatiana Da Ros、Giampiero Spalluto、Jan Balzarini、Maurizio Prato

  DOI：10.1016/j.bmcl.2003.09.016

  日期：2003.12

  A new series of bis-functionalized fullerene C(60) derivatives bearing two or more solubilizing chains have been evaluated for their activity against HIV-1 and HIV-2 strains. Some of the compounds show activity against HIV-1 type in the low micromolar range. The effect of the positions of the addends on the C(60) nucleus has been investigated, indicating that only trans-2 isomers possess promising activity. The presence of a quaternary pyrrolidinium nitrogen is essential to increase solubility. (C) 2003 Elsevier Ltd. All rights reserved.
• Palladium(II)-induced Alkali Metal Ion Incorporation of 2,6-Disubstituted Pyridines with Bis(alkoxyethyl) Malonate Subunits
  作者：Tomoko Mutou、Kiichi Amimoto、Hajime Kanatomi、Hiroyuki Koyama、Toshio Kawato

  DOI：10.1246/cl.1999.1231

  日期：1999.11

  A series of 2,6-bis(2,2′-dicarbalkoxyethyl)pyridine ligands were prepared. A couple of the ligands linked by a trans-PdCl2 unit extracted alkali metal ions from an aqueous media into a chloroform media, while a single pyridine ligand did not work as an extractive reagent.

  制备了一系列 2,6-双（2,2′-二烷氧基乙基）吡啶配体。其中几个配体通过反式-钯-Cl2 单元连接，可将碱金属离子从水介质萃取到氯仿介质中，而单个吡啶配体则不能作为萃取试剂。