2-[2-[2-[2-[2-[2-[2-[2-[2-[2-(2-Phenylmethoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxymethylbenzene | 349113-91-3

• 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: 2-[2-[2-[2-[2-[2-[2-[2-[2-[2-(2-Phenylmethoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxymethylbenzene
• CAS: 349113-91-3
• 化学式: C₃₆H₅₈O₁₂
• 分子量: 682.849
• InChiKey: CSNDUNISCZVWPO-UHFFFAOYSA-N

物化性质

• 沸点：
  691.8±50.0 °C(Predicted)
• 密度：
  1.097±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  48
• 可旋转键数：
  37
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  111
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  2-[2-[2-[2-[2-[2-[2-[2-[2-[2-(2-Phenylmethoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxymethylbenzene 在 palladium on activated charcoal 盐酸 、 sodium azide 、 氢气 、 sodium hydride 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 36.0h， 生成 N1-(62-amino-3,6,9,12,15,18,21,24,27,30,33,36,39,42,45,48,51,54,57,60-icosaoxadohexacontyl)-N6-(4-sulfamoylbenzyl)adipamide
  参考文献：
  名称：

  Dependence of Effective Molarity on Linker Length for an Intramolecular Protein−Ligand System

  摘要：

  This paper reports dissociation constants and "effective molarities" (M-eff) for the intramolecular binding of a ligand covalently attached to the surface of a protein by oligo(ethylene glycol) (EG(n)) linkers of different lengths (n = 0, 2, 5, 10, and 20) and compares these experimental values with theoretical estimates from polymer theory. As expected, the value of M-eff is lowest when the linker is too short (n = 0) to allow the ligand to bind noncovalently at the active site of the protein without strain, is highest when the linker is the optimal length (n = 2) to allow such binding to occur, and decreases monotonically as the length increases past this optimal value (but only by a factor of similar to 8 from n = 2 to n = 20). These experimental results are not compatible with a model in which the single bonds of the linker are completely restricted when the ligand has bound noncovalently to the active site of the protein, but they are quantitatively compatible with a model that treats the linker as a random-coil polymer. Calorimetry revealed that enthalpic interactions between the linker and the protein are not important in determining the thermodynamics of the system. Taken together, these results suggest that the manifestation of the linker in the thermodynamics of binding is exclusively entropic. The values of M-eff are, theoretically, intrinsic properties of the EG(n) linkers and can be used to predict the avidities of multivalent ligands with these linkers for multivalent proteins. The weak dependence of M-eff on linker length suggests that multivalent ligands containing flexible linkers that are longer than the spacing between the binding sites of a multivalent protein will be effective in binding, and that the use of flexible linkers with lengths somewhat greater than the optimal distance between binding sites is a justifiable strategy for the design of multivalent ligands.

  DOI：

  10.1021/ja066780e
• 作为产物：
  描述：

  二乙二醇单甲醚 在 potassium tert-butylate 、 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 15.5h， 生成 2-[2-[2-[2-[2-[2-[2-[2-[2-[2-(2-Phenylmethoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxymethylbenzene
  参考文献：
  名称：

  接近单分散性的聚环氧乙烷的合成

  摘要：

  聚合物中的多分散性妨碍了对其结构-性质关系的基本了解，并阻碍了它们在医学等领域使用，因为多分散性会影响生物活性。相对短链的聚环氧乙烷[（CH 2 CH 2 O 2）n的多分散性; [PEO]影响其生物学活性，例如，PEO酰化药物的毒性和功效。结果，已经进行了巨大的努力以尽可能降低分散度（不可能真正地单分散的材料）。在这里，我们报告了一种合成程序，该程序导致了前所未有的低分散度。我们还首次表明，可以区分只有一个环氧乙烷（EO）单元不同的PEO，这对于验证此处实现的极低分散度至关重要。预计接近单分散性的聚环氧乙烷的合成将在许多应用中对摩尔质量的分布敏感的领域中具有价值。

  DOI：

  10.1002/anie.201403436

文献信息

• Synthesis of Oligo(ethylene glycol) toward 44-mer
  作者：Saleh A. Ahmed、Mutsuo Tanaka

  DOI：10.1021/jo0617464

  日期：2006.12.1

  A synthetic method for oligo(ethylene glycol) toward 44-mer (FW = 1956.35) is described. Reiteration of Williamson's ether synthesis and hydrogenation to remove protecting benzyl group affords desired oligo(ethylene glycol) toward 44-mer in moderate yields. The advantages in this method are use of commercially easily available materials as starting materials and procedures avoiding difficulty in purification

  描述了一种低聚（乙二醇）向44聚体（FW = 1956.35）的合成方法。重复威廉姆森的醚合成和氢化以除去保护的苄基，以中等收率向44-聚体提供所需的寡聚（乙二醇）。该方法的优点是使用市售易得的材料作为起始材料和方法，从而避免了尽可能多地纯化产物的困难。
• Synthesis of Poly(ethylene oxide) Approaching Monodispersity
  作者：Krzysztof Maranski、Yuri G. Andreev、Peter G. Bruce

  DOI：10.1002/anie.201403436

  日期：2014.6.16

  of dispersity. We also show for the first time that it is possible to discriminate between PEOs differing in only 1 ethylene oxide (EO) unit, essential in order to verify the exceptionally low levels of dispersity achieved here. It is anticipated that the synthesis of poly(ethylene oxide) approaching monodispersity will be of value in many fields where the applications are sensitive to the distribution

  聚合物中的多分散性妨碍了对其结构-性质关系的基本了解，并阻碍了它们在医学等领域使用，因为多分散性会影响生物活性。相对短链的聚环氧乙烷[（CH 2 CH 2 O 2）n的多分散性; [PEO]影响其生物学活性，例如，PEO酰化药物的毒性和功效。结果，已经进行了巨大的努力以尽可能降低分散度（不可能真正地单分散的材料）。在这里，我们报告了一种合成程序，该程序导致了前所未有的低分散度。我们还首次表明，可以区分只有一个环氧乙烷（EO）单元不同的PEO，这对于验证此处实现的极低分散度至关重要。预计接近单分散性的聚环氧乙烷的合成将在许多应用中对摩尔质量的分布敏感的领域中具有价值。
• Dependence of Effective Molarity on Linker Length for an Intramolecular Protein−Ligand System
  作者：Vijay M. Krishnamurthy、Vincent Semetey、Paul J. Bracher、Nan Shen、George M. Whitesides

  DOI：10.1021/ja066780e

  日期：2007.2.1

  This paper reports dissociation constants and "effective molarities" (M-eff) for the intramolecular binding of a ligand covalently attached to the surface of a protein by oligo(ethylene glycol) (EG(n)) linkers of different lengths (n = 0, 2, 5, 10, and 20) and compares these experimental values with theoretical estimates from polymer theory. As expected, the value of M-eff is lowest when the linker is too short (n = 0) to allow the ligand to bind noncovalently at the active site of the protein without strain, is highest when the linker is the optimal length (n = 2) to allow such binding to occur, and decreases monotonically as the length increases past this optimal value (but only by a factor of similar to 8 from n = 2 to n = 20). These experimental results are not compatible with a model in which the single bonds of the linker are completely restricted when the ligand has bound noncovalently to the active site of the protein, but they are quantitatively compatible with a model that treats the linker as a random-coil polymer. Calorimetry revealed that enthalpic interactions between the linker and the protein are not important in determining the thermodynamics of the system. Taken together, these results suggest that the manifestation of the linker in the thermodynamics of binding is exclusively entropic. The values of M-eff are, theoretically, intrinsic properties of the EG(n) linkers and can be used to predict the avidities of multivalent ligands with these linkers for multivalent proteins. The weak dependence of M-eff on linker length suggests that multivalent ligands containing flexible linkers that are longer than the spacing between the binding sites of a multivalent protein will be effective in binding, and that the use of flexible linkers with lengths somewhat greater than the optimal distance between binding sites is a justifiable strategy for the design of multivalent ligands.