3,4,5-tris(2-(2-methoxyethoxy)ethoxy)benzaldehyde | 422267-98-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3,4,5-tris(2-(2-methoxyethoxy)ethoxy)benzaldehyde
• 英文别名: (3,4,5-tris(2-(2-methoxyethoxy)ethoxy)phenyl)methanol；3,4,5-Tris[2-(2-methoxyethoxy)ethoxy]benzaldehyde
• CAS: 422267-98-9
• 化学式: C₂₂H₃₆O₁₀
• 分子量: 460.522
• InChiKey: ZGIGFEKFDFYZDH-UHFFFAOYSA-N

物化性质

• 沸点：
  552.6±50.0 °C(Predicted)
• 密度：
  1.124±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：
  22
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  100
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  3,4,5-tris(2-(2-methoxyethoxy)ethoxy)benzaldehyde 在 methyl (8S)-8-(chloromethyl)-6-[5,7-dimethoxy-6-[2-(2-methoxyethoxy)ethoxy]-1H-indole-2-carbonyl]-4-hydroxy-7,8-dihydro-3H-pyrrolo[3,2-e]indole-2-carboxylate 、 水 、 sodium methylate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 、 5,5-dimethyl-1,3-cyclohexadiene 、 N,N-二甲基甲酰胺 为溶剂， 反应 42.0h， 生成 methyl (8S)-8-(chloromethyl)-4-hydroxy-6-[5,6,7-tris[2-(2-methoxyethoxy)ethoxy]-1H-indole-2-carbonyl]-7,8-dihydro-3H-pyrrolo[3,2-e]indole-2-carboxylate
  参考文献：
  名称：

  Duocarmycin 类 DNA 烷基化抗肿瘤药物的疏水特性与生物活性之间的基本关系：疏水结合驱动的结合

  摘要：

  Duocarmycin SA 的两个系统系列越来越亲水，其特征是将乙二醇单元（n = 1-5）并入三甲氧基吲哚亚基的甲氧基取代基中。随着乙二醇单元掺入的增加，这些衍生物表现出逐渐增加的水溶性以及细胞生长抑制活性和 DNA 烷基化效率的逐渐降低。观察到 cLogP 与细胞生长抑制的-log IC 50和 -log AE（AE = 无细胞 DNA 烷基化效率）的线性关系，cLogP值跨越 2.5–0.49 的生产范围，-log IC 50值跨越11.2-6.4的范围，代表IC 50值相差 10 5 (0.008 到 370 nM)。结果量化了化合物的疏水特性在表达此类成员的生物活性（驱动本质上可逆的 DNA 烷基化反应）中所起的基本作用，并定义了其影响的惊人程度。

  DOI：

  10.1021/jm400665c
• 作为产物：
  描述：

  3,4,5-tris(1,4,7-trioxaoctyl)benzyl alcohol 在 manganese(IV) oxide 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以93%的产率得到3,4,5-tris(2-(2-methoxyethoxy)ethoxy)benzaldehyde
  参考文献：
  名称：

  一种具有三重刺激响应性的小分子AIEE发光 材料及其制备方法

  摘要：

  本发明公开了一种具有三重刺激响应性的小分子AIEE发光材料及其制备方法。该小分子发光材料以对甲苯磺酰氯、没食子酸甲酯、对羟基苯乙腈等为原料，经取代、氧化、还原、Knoevenagel缩合等反应制备而成。该材料不仅表现出典型的聚集诱导荧光增强效应，同时还表现出对温度、碱、紫外光的敏感行为，在碱性物质的分析检测、温度传感器、智能开关、药物的可控释放、光响应发光材料等领域均具有潜在的应用价值。

  公开号：

  CN108558701B

文献信息

• Solvent-resolved fluorescent Ag nanocrystals capped with a novel terpyridine-based dye
  作者：Yuanhao Gao、Jieying Wu、Qiong Zhao、Lingxia Zheng、Hongping Zhou、Shengyi Zhang、Jiaxiang Yang、Yupeng Tian

  DOI：10.1039/b815115f

  日期：——

  By using a novel terpyridine-based dye as a surface stabilizing agent, novel dye-capped Ag nanocrystals (NCs) were obtained. The growth dynamics of these dye-capped Ag NCs were monitored by UV-vis absorption spectroscopy. Interactions between the dye and the Ag NCs were investigated by 1H NMR spectroscopy. The dye-capped Ag NCs showed solvent-resolved fluorescence in organic solvents, with full width at half-maximums (FWHM) as wide as ∼100 nm, demonstrating the effect of the Ag NCs on the enhanced fluorescence of the capping dye.

  通过使用一种新型的基于萜吡啶的染料作为表面稳定剂，获得了新型染料包裹的银纳米晶体（NCs）。紫外可见吸收光谱监测了这些染料包裹的银纳米晶体的生长动态。通过 1H NMR 光谱研究了染料与 Ag NCs 之间的相互作用。染料封端的 Ag NCs 在有机溶剂中显示出溶剂分辨荧光，半最大值全宽（FWHM）宽达 ∼ 100 nm，证明了 Ag NCs 对封端染料荧光增强的影响。
• A Template‐free Pd2L4 Cage with up to Nanomolar Affinity for Chloride in Aqueous Solutions
  作者：Vellaiyadevan Sivalingam、Shobhana Krishnaswamy、Dillip Kumar Chand

  DOI：10.1002/chem.202300891

  日期：——

  Halide catcher: A template-free, water-soluble Pd2L4 cage that binds chloride with up to nanomolar affinity in aqueous solutions is reported here. Of the most abundant essential anions present in living organisms, this cage exclusively binds chloride. This unprecedented binding affinity/selectivity was achieved by making the best use of hydrogen bonding and electrostatic interactions.

  卤化物捕集器：此处报道了一种无模板、水溶性 Pd 2 L 4笼，它在水溶液中以高达纳摩尔的亲和力结合氯化物。在生物体中存在的最丰富的必需阴离子中，这个笼子专门结合氯离子。这种前所未有的结合亲和力/选择性是通过充分利用氢键和静电相互作用实现的。
• Highly Ordered Assembly of π-Stacked Distyrylbenzenes by Oligoadenines
  作者：Wanggui Yang、Ping Fang Xia、Man Shing Wong

  DOI：10.1021/ol101571h

  日期：2010.9.17

  A well-defined nanofibrous structure with lengths of several hundred nanometers and cross-sectional width of a single size (similar to 6 +/- 0.5 nm) was self-assembled by oligoadenines, dA(20), and thymine-appended distyrylbenzene through binary complementary A-T hydrogen bond formation and the strong pi-pi stacking interactions. This demonstrated a useful supramolecular self-assembling approach to control the packing order of pi-conjugated molecules and provided a practical means to enhance the optical properties of a material.
• THE INFLUENCE OF POLYETHER SUBSTITUENTS ON BIOLOGICAL ACTIVITY OF CURCUMIN DERIVATIVES
  作者：Beata Gruber、Deptuła Tomasz、Krówczyński Adam、Bubko Irena

  DOI：10.32383/appdr/112859

  日期：2020.2.29

  Curcumin is reported as an anti-proliferative and chemopreventive compound. However, it shows poor water solubility, low bioavailability, and rapid metabolism. To address these problems, curcumin derivatives substituted with polyether chain were synthesized to improve the hydrophilicity of curcumin and thus its bioavailability. The biological activity of modified curcumin molecules were studied with human normal B-lymphocytes GM 14667 and human leukemia cells HL60 and covered: the denotation of IC50 values for each new compound with use of MTT test and the studies on apoptosis induction observed as morphological changes and the expression of apoptotic proteins, BAX, BCL-2 and survivin with use of Western Blot analysis. All effects were referenced to native curcumin. The derivatives with modified polyether chains number and the position of methoxy groups were selected for further studies. As was shown, the solubility of the compound does not directly correlate with its cytotoxicity. The maintenance of the methoxy group in the meta position, as well as the introduction of hydrophilic polyether chains but not the number of polyether chains, may affect the cytotoxic activity of curcumin derivatives against cancer cells. Modifications of the curcumin molecule structure can determine its impact on the profile of pro- or anti-apoptotic proteins.