isopropylidene-[G-2]-benzyl ester | 199457-34-6

• 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: isopropylidene-[G-2]-benzyl ester
• 英文别名: 2-((benzyloxy)carbonyl)-2-methylpropane-1,3-diyl bis(3-hydroxy-2-(hydroxymethyl)-2-methylpropanoate)；[2-[[3-Hydroxy-2-(hydroxymethyl)-2-methylpropanoyl]oxymethyl]-2-methyl-3-oxo-3-phenylmethoxypropyl] 3-hydroxy-2-(hydroxymethyl)-2-methylpropanoate；[2-[[3-hydroxy-2-(hydroxymethyl)-2-methylpropanoyl]oxymethyl]-2-methyl-3-oxo-3-phenylmethoxypropyl] 3-hydroxy-2-(hydroxymethyl)-2-methylpropanoate
• CAS: 199457-34-6
• 化学式: C₂₂H₃₂O₁₀
• 分子量: 456.49
• InChiKey: YGELYMMLOVMXMT-UHFFFAOYSA-N

物化性质

• 沸点：
  625.6±50.0 °C(Predicted)
• 密度：
  1.289±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  32
• 可旋转键数：
  16
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  160
• 氢给体数：
  4
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  isopropylidene-[G-2]-benzyl ester 在 palladium 10% on activated carbon 、 N,N'-二环己基碳二亚胺 、 DPTS 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 53.0h， 生成 dendron 3
  参考文献：
  名称：

  两亲性 Janus 树枝状聚合物在水中的自组装行为：实验和粗粒度分子动力学模拟相结合的方法。

  摘要：

  两亲性 Janus 树枝状聚合物 (JD) 是具有亲水性和疏水性成分的重复支化分子，可在水中自组装形成各种形态，包括类似于脂质体的囊泡，具有潜在的药物和医疗应用。迄今为止，JD 的自组装尚未得到充分研究，因此深入了解其机制以及对 JD 分子结构的依赖性非常重要。在这项研究中，使用实验和计算方法评估了第二代双-MPA JD 在水中的聚集行为。使用薄膜水合和乙醇注射方法将 JD 分散在水中。通过动态光散射、共焦显微镜和原子力显微镜对所得组件进行了表征。此外，还进行了粗粒度分子动力学（CG-MD）模拟来研究JDs聚集的机制。实验表征和 CG-MD 模拟证实了在水中获得无叉指双层的组装体。使用乙醇注射方法获得具有树枝状聚合物特征的组装体。这项研究的结果建立了 JD 的分子结构与其在水中聚集体的特性之间的关系。因此，我们的研究结果可能与设计具有适合药物输送系统的定制组件的新型 JD 相关。

  DOI：

  10.3390/molecules23040969
• 作为产物：
  描述：

  苄基3-羟基-2-(羟基甲基)-2-甲基丙酸酯 在 4-二甲氨基吡啶 、 硫酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 isopropylidene-[G-2]-benzyl ester
  参考文献：
  名称：

  Degradable Self-Assembling Dendrons for Gene Delivery: Experimental and Theoretical Insights into the Barriers to Cellular Uptake

  摘要：

  This paper uses a combined experimental and theoretical approach to gain unique insight into gene delivery. We report the synthesis and investigation of a new family of second-generation dendrons with four triamine surface ligands capable of binding to DNA, degradable aliphatic-ester dendritic scaffolds, and hydrophobic units at their focal points. Dendron self-assembly significantly enhances DNA binding as monitored by a range of experimental methods and confirmed by multiscale modeling. Cellular uptake studies indicate that some of these dendrons are highly effective at transporting DNA into cells (ca. 10 times better than poly(ethyleneimine), PEI). However, levels of transgene expression are relatively low (ca. 10% of PEI). This indicates that these dendrons cannot navigate all of the intracellular barriers to gene delivery. The addition of chloroquine indicates that endosomal escape is not the limiting factor in this case, and it is shown, both experimentally and theoretically, that gene delivery can be correlated with the ability of the dendron assemblies to release DNA. Mass spectrometric assays demonstrate that the dendrons, as intended, do degrade under biologically relevant conditions over a period of hours. Multiscale modeling of degraded dendron structures suggests that complete dendron degradation would be required for DNA release. Importantly, in the presence of the lower pH associated with endosomes, or when bound to DNA, complete degradation of these dendrons becomes ineffective on the transfection time scale we propose this explains the poor transfection performance of these dendrons. As such, this paper demonstrates that taking this kind of multidisciplinary approach can yield a fundamental insight into the way in which dendrons can navigate barriers to cellular uptake. Lessons learned from this work will inform future dendron design for enhanced gene delivery.

  DOI：

  10.1021/ja2070736

文献信息

• Synthesis, Characterization, and Thermal Behavior of Steroidal Dendrons
  作者：Jarmo Ropponen、Jari Tamminen、Manu Lahtinen、Juha Linnanto、Kari Rissanen、Erkki Kolehmainen

  DOI：10.1002/ejoc.200400416

  日期：2005.1

  (UDCA), deoxycholic acid (DCA), and cholic acid (CA). The thermal behavior of the steroidal dendrons was characterized by differential scanning calorimetry (DSC) and by thermogravimetric analysis (TGA). Finally, quantum chemical calculation methods were used to study the geometries of the dendrons and the occurrence of intramolecular hydrogen bonds in these dendritic molecules. (© Wiley-VCH Verlag GmbH

  通过使用2,2-双（羟甲基）丙酸作为重复单元，以收敛方式合成了一系列第一代和第二代新型树枝状甾族聚酯。通过使用四种胆汁酸：石胆酸 (LCA)、熊去氧胆酸 (UDCA)、脱氧胆酸 (DCA) 和胆酸 (CA) 产生了具有各种表面修饰的第一代和第二代羟基官能化树突）。通过差示扫描量热法 (DSC) 和热重分析 (TGA) 表征了甾体树突的热行为。最后，利用量子化学计算方法研究了树枝状分子的几何形状和这些树枝状分子中分子内氢键的发生情况。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)
• Effect of Multivalency on the Performance of Enantioselective Separation Media for Chiral HPLC Prepared by Linking Multiple Selectors to a Porous Polymer Support via Aliphatic Dendrons
  作者：Frank H. Ling、Victor Lu、Frantisek Svec、Jean M. J. Fréchet

  DOI：10.1021/jo011005x

  日期：2002.4.1

  multivalent dendritic linker to monodisperse macroporous poly(2-hydroxyethyl methacrylate-co-ethylene dimethacrylate) beads have been prepared using two different approaches. The convergent method involves the preparation of ligands in solution and their subsequent attachment to the support. The divergent approach is based on the stepwise "on-bead" formation of the linker using methods that are typical

  已经使用两种不同方法制备了包含L-脯氨酸茚满苯胺内酯手性选择剂的手性固定相（CSP），该手性固定剂通过多价树状连接基连接到单分散的大孔聚（甲基丙烯酸2-羟乙基酯-二甲基丙烯酸乙烯酯-共-乙烯）珠上。收敛方法涉及溶液中配体的制备及其随后与载体的连接。发散方法基于使用固相合成的典型方法的接头的逐步“珠上”形成。尽管会聚的CSP具有明确定义的配体，但它们的负载相对较低。相反，发散技术为CSP提供了更高的负载量，但对精确配体结构的控制更为有限。
• Dendritic Oxazoline Ligands in Enantioselective Palladium-Catalyzed Allylic Alkylations
  作者：Michael Malkoch、Kristina Hallman、Serghey Lutsenko、Anders Hult、Eva Malmström、Christina Moberg

  DOI：10.1021/jo0200116

  日期：2002.11.1

  attached to 2-(hydroxymethyl)pyridinooxazoline and bis[4-(hydroxymethyl)oxazoline] compounds. The new ligands obtained were assessed in palladium-catalyzed allylic alkylations. The first type of ligands exhibited enantioselectivity similar to that of a benzoyl ester derivative, whereas the latter type of ligands afforded products with higher selectivity than the analogous benzoyl ester. The activity of the

  将基于2,2-双（羟甲基）丙酸和（1R，2S，5R）-薄荷氧基乙酸的第一至第四代树状取代基连接至2-（羟甲基）吡啶并恶唑啉和双[4-（羟甲基）恶唑啉]化合物。在钯催化的烯丙基烷基化反应中评估获得的新配体。第一种配体表现出与苯甲酸酯衍生物相似的对映选择性，而后一种配体提供了比类似苯甲酸酯更高选择性的产物。树突状催化剂的活性随着生成的增加而降低。
• Functional Carbazole Liquid-Crystal Block Codendrimers with Optical and Electronic Properties
  作者：Ismael Gracia、Beatriz Feringán、José Luis Serrano、Roberto Termine、Attilio Golemme、Ana Omenat、Joaquín Barberá

  DOI：10.1002/chem.201404555

  日期：2015.1.12

  family of block codendrimers consisting of highly versatile mesogenic and carbazole‐containing 2,2‐bis(hydroxymethyl)propionic acid (bis‐MPA) dendrons are reported. The liquid‐crystal behaviour was investigated by means of differential scanning calorimetry, polarised‐light optical microscopy and X‐ray diffraction. Depending on the chemical structure of the constituent dendrons, the codendrimers show lamellar

  据报道，由高度通用的介晶和含咔唑的2,2-双（羟甲基）丙酸（bis-MPA）树突组成的嵌段共修饰分子家族的合成与表征。通过差示扫描量热法，偏光光学显微镜和X射线衍射研究了液晶行为。根据组成树突的化学结构，共生分子显示出层状或柱状中间相。根据实验结果，提出了分子水平和中间相的模型。研究了咔唑部分在其结构中的存在所产生的嵌段共聚体的物理性质：溶液和中间相中的光致发光，电化学行为和空穴传输。
• Polyester-Based Carborane-Containing Dendrons
  作者：Kristin M. Galie、Alexis Mollard、Ilya Zharov

  DOI：10.1021/ic060866r

  日期：2006.9.1

  New carborane-containing dendrons based on a 2,2-bis(hydroxymethyl) propanoic acid scaffold have been prepared for applications in boron neutron capture therapy. A generation-2 carborane-containing dendron carrying 40 boron atoms was the highest generation synthetically available due to the steric crowding. The structure of this dendron has been simulated by molecular dynamics. A 10-carbon linker carrying a carboxylic group has been installed at the focal point of the dendron to distance the attachment point from the sterically hindered core.