2-[2-[2-(2-羟基乙氧基)乙氧基]乙氧基]苯甲酸乙酯 | 127017-97-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-[2-[2-(2-羟基乙氧基)乙氧基]乙氧基]苯甲酸乙酯
• 英文名称: tetraethylene glycol monobenzoate
• 英文别名: 2,5,8,11-Tetraoxatridecan-13-ol, 1-oxo-1-phenyl-；2-[2-[2-(2-hydroxyethoxy)ethoxy]ethoxy]ethyl benzoate
• CAS: 127017-97-4
• 化学式: C₁₅H₂₂O₆
• 分子量: 298.336
• InChiKey: WHHVSGJUOCTHJP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  21
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-[2-[2-(2-羟基乙氧基)乙氧基]乙氧基]苯甲酸乙酯 在 N-溴代丁二酰亚胺(NBS) 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 以97%的产率得到Benzoic acid 2-{2-[2-(2-bromo-ethoxy)-ethoxy]-ethoxy}-ethyl ester
  参考文献：
  名称：

  Kinetic Stabilization of an Oligomeric Protein by a Single Ligand Binding Event

  摘要：

  Protein native state stabilization imposed by small molecule binding is an attractive strategy to prevent the misfolding and misassembly processes associated with amyloid diseases. Transthyretin (TTR) amyloidogenesis requires rate-limiting tetramer dissociation before misassembly of a partially denatured monomer ensues. Selective stabilization of the native TTR tetramer over the dissociative transition state by small molecule binding to both thyroxine binding sites raises the kinetic barrier of tetramer dissociation, preventing amyloidogenesis. Assessing the amyloidogenicity of a TTR tetramer having only one amyloidogenesis inhibitor (1) bound is challenging because the two small molecule binding constants are generally not distinct enough to allow for the exclusive formation of (TTRI)-I-. in solution to the exclusion of (TTRI2)-I-. and unliganded TTR. Herein, we report a method to tether one fibril formation inhibitor to TTR by disulfide bond formation. Occupancy of only one of the two thyroxine binding sites is sufficient to inhibit tetramer dissociation in 6.0 M urea and amyloidogenesis under acidic conditions by imposing kinetic stabilization on the entire tetramer. The sufficiency of single occupancy for stabilizing the native state of TTR provides the incentive to search for compounds displaying striking negative binding cooperativity (e.g., K-d1 in nanomolar range and K-d2 in the micromolar to millimolar range), enabling lower doses of inhibitor to be employed in the clinic, mitigating potential side effects.

  DOI：

  10.1021/ja042929f
• 作为产物：
  描述：

  在 硫酸 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 2-[2-[2-(2-羟基乙氧基)乙氧基]乙氧基]苯甲酸乙酯
  参考文献：
  名称：

  通过低聚乙二醇的高环化高效合成单分散聚乙二醇及其衍生物

  摘要：

  已开发出一种基于大环硫酸盐（MCS）的单分散聚乙二醇（M-PEG）及其单官能化衍生物的方法。寡聚乙二醇（OEG）的大环化提供了MCS（最多62个成员的大环），作为一系列单官能化M-PEG的通用前体。通过MCS的反复亲核开环反应而无需进行基团保护和激活，可以轻松制备一系列M-PEG，包括史无前例的64-mer（2850 Da）。合成简单性与这种新策略的多功能性可能为M-PEG的更广泛应用铺平道路。

  DOI：

  10.1002/anie.201410309

文献信息

• Investigation of the origin and synthetic application of the pseudodilution effect for Pd-catalyzed macrocyclisations in concentrated solutions with immobilized catalysts
  作者：Elisabeth Brehm、Rolf Breinbauer

  DOI：10.1039/c3ob41020j

  日期：——

  Immobilized Pd-complexes allowed macrocyclisations via the Tsuji-Trost-reaction in concentrated solutions. Systematic studies suggest that the origin of this pseudodilution effect is neither film diffusion nor gel diffusion, but the reduction in conformational freedom of intermediates and intramolecular prenucleophile activation. In contrast a pseudodilution effect could not be observed for Sonogashira-

  固定的Pd复合物可以通过Tsuji-Trost反应在浓缩溶液中进行大环化。系统研究表明，这种假稀释作用的起源既不是膜扩散也不是凝胶扩散，而是中间体构象自由度的降低和分子内亲核试剂的活化。相反，对于Sonogashira-和Suzuki-大环化没有观察到假稀释作用。
• Spacer optimization of new conjugates for a melanoma-selective delivery approach
  作者：Mathieu André、Sébastien Tarrit、Marie-Joelle Couret、Marie-Josèphe Galmier、Eric Débiton、Jean-Michel Chezal、Emmanuelle Mounetou

  DOI：10.1039/c3ob41428k

  日期：——

  designed and synthesized seven conjugates varying the structure of the linker connecting the 5-iodo-2′-deoxyuridine (IUdR) to the ICF 01012 melanoma-carrier for potential intratumoural specific drug release. Chemical and in vitro metabolic stability evaluations showed that, except for the ester conjugate (1), the ketal (2b), acetal (2a), carbonate (4) and carbamate (3) conjugates were compatible with our

  在寻找更具选择性的抗癌药物中，我们设计并合成了7种偶联物，这些偶联物改变了将5-碘2'-脱氧尿苷（IUdR）连接到ICF 01012黑色素瘤载体的连接子的结构，以实现潜在的肿瘤内特异性药物释放。化学和体外代谢稳定性评估表明，除酯缀合物（1）外，缩酮（2b），乙缩醛（2a），碳酸盐（4）和氨基甲酸酯（3）缀合物与我们的方法兼容。缩醛（2a）及其聚乙二醇化衍生物（2c）对于进一步的体内发育特别感兴趣。 由于它们各自的pH依赖性稳定性和有限的代谢降解作用而导致细胞的发育，以便利用恶性黑素细胞的酸性亚细胞环境在细胞内化后触发治疗剂的释放。
• Micro-flow photosynthesis of new dienophiles for inverse-electron-demand Diels–Alder reactions. Potential applications for pretargeted in vivo PET imaging
  作者：Emilie M. F. Billaud、Elnaz Shahbazali、Muneer Ahamed、Frederik Cleeren、Timothy Noël、Michel Koole、Alfons Verbruggen、Volker Hessel、Guy Bormans

  DOI：10.1039/c6sc02933g

  日期：——

  bioorthogonal inverse-electron-demand Diels–Alder (IEDDA) reaction between tetrazines and trans-cyclooctene (TCO) derivatives. We aimed to develop new [18F]TCO–dienophiles with high reactivity for IEDDA reactions, and favorable in vivo stability and pharmacokinetics. New dienophiles were synthesized using an innovative micro-flow photochemistry process, and their reaction kinetics with a tetrazine were determined

  预靶向 PET 成像已成为一种有效的两步体内方法，它将抗体的卓越亲和力和选择性与短寿命放射性核素放射性标记的小分子的快速药代动力学和有利的剂量测定相结合。该方法可以基于四嗪和反式环辛烯（TCO）衍生物之间的生物正交逆电子需求狄尔斯-阿尔德（IEDDA）反应。我们的目标是开发新的[ 18 F]TCO-亲双烯体，其对 IEDDA 反应具有高反应性，并且具有良好的体内稳定性和药代动力学。使用创新的微流光化学工艺合成了新的亲二烯体，并测定了它们与四嗪的反应动力学。研究了最有前途的18 F-放射性标记-TCO 衍生物 ( [ 18 F]3 ) 的体内稳定性和生物分布，并在荷瘤小鼠中评估了其体内预靶向 PET 成像的潜力。我们证明[ 18 F]3是适合IEDDA 反应和预靶向应用的亲双烯体。
• Synthesis of a Novel D-Glucose-Conjugated 15-Crown-5 Ether with a Spiro Ketal Structure
  作者：Takashi Yamanoi、Yoshiki Oda、Hitomi Muraishi、Sho Matsuda

  DOI：10.3390/molecules13081840

  日期：——

  This paper describes a synthetic approach to a novel D-glucose-conjugated 15-crown-5 ether having a spiroketal structure starting from a 1-C-vinylated glucose derivative. The approach consists of the glycosylation of the vinylated glucose derivative to give an ethyleneoxy spacer derivative using bismuth(III) triflate, the conversion of the 1-C-vinyl group of the glucoside produced into a carboxylic

  本文描述了一种新型 D-葡萄糖结合的 15-冠-5 醚的合成方法，该醚具有从 1-C-乙烯基化葡萄糖衍生物开始的 spiroketal 结构。该方法包括使用三氟甲磺酸铋 (III) 对乙烯基化葡萄糖衍生物进行糖基化以得到亚乙基氧基间隔基衍生物，将产生的葡萄糖苷的 1-C-乙烯基转化为羧酸基团，以及亚乙基氧基间隔基团中的羧基和末端羟基。由此成功合成了具有独特螺缩酮结构的D-葡萄糖缀合的15-冠-5醚。
• Al2O3/MeSO3H (AMA) as a new reagent with high selective ability for monoesterification of diols
  作者：Hashem Sharghi、Mona Hosseini Sarvari

  DOI：10.1016/s0040-4020(03)00518-0

  日期：2003.5

  A new facile method for moncesterification of diols has been developed. A variety of diols, in particular oligoethylene glycols, were selectively monoesterified in excellent yields by reaction with aromatic and aliphatic acids in the presence Of Al2O3/MeSO3H as a new reagent without use of any solvents. (C) 2003 Elsevier Science Ltd. All rights reserved.