2-((4-(2-bromoethoxy)-3-methoxybenzyl)-oxy)tetrahydro-2H-pyran | 347894-40-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-((4-(2-bromoethoxy)-3-methoxybenzyl)-oxy)tetrahydro-2H-pyran
• 英文别名: 2-{[4-(2-bromoethoxy)-3-methoxybenzyl]-oxy}tetrahydro-2H-pyran；2-[4-(2-Bromoethoxy)-3-methoxybenzyloxy]tetrahydropyran；[4-(2-bromoethoxy)-3-methoxybenzyloxy]tetrahydropyran；2H-Pyran, 2-[[4-(2-bromoethoxy)-3-methoxyphenyl]methoxy]tetrahydro-；2-[[4-(2-bromoethoxy)-3-methoxyphenyl]methoxy]oxane
• CAS: 347894-40-0
• 化学式: C₁₅H₂₁BrO₄
• 分子量: 345.233
• InChiKey: VUTMEBYYFXQHIN-UHFFFAOYSA-N

物化性质

• 沸点：
  423.4±45.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-((4-(2-bromoethoxy)-3-methoxybenzyl)-oxy)tetrahydro-2H-pyran 在 四(三苯基膦)钯 、 potassium peroxomonocarbonate 、 三正丁基氢锡 、 四丁基碘化铵 、 potassium carbonate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 17.5h， 生成 [3-Prop-2-enoxy-4-[2-[[6,13,20-trimethoxy-12,19-bis[2-[2-methoxy-4-(oxan-2-yloxymethyl)phenoxy]ethoxy]-5-tetracyclo[15.4.0.03,8.010,15]henicosa-1(21),3,5,7,10,12,14,17,19-nonaenyl]oxy]ethoxy]phenyl]methanol
  参考文献：
  名称：

  Development of a Functionalized Xenon Biosensor

  摘要：

  NMR-based biosensors that utilize laser-polarized xenon offer potential advantages beyond current sensing technologies. These advantages include the capacity to simultaneously detect multiple analytes, the applicability to in vivo spectroscopy and imaging, and the possibility of "remote" amplified detection. Here, we present a detailed NMR characterization of the binding of a biotin-derivatized caged-xenon sensor to avidin. Binding of "functionalized" xenon to avidin leads to a change in the chemical shift of the encapsulated xenon in addition to a broadening of the resonance, both of which serve as NMR markers of ligand-target interaction. A control experiment in which the biotin-binding site of avidin was blocked with native biotin showed no such spectral changes, confirming that only specific binding, rather than nonspecific contact, between avidin and functionalized xenon leads to the effects on the xenon NMR spectrum. The exchange rate of xenon (between solution and cage) and the xenon spin-lattice relaxation rate were not changed significantly upon binding. We describe two methods for enhancing the signal from functionalized xenon by exploiting the laser-polarized xenon magnetization reservoir. We also show that the xenon chemical shifts are distinct for xenon encapsulated in different diastereomeric cage molecules. This demonstrates the potential for tuning the encapsulated xenon chemical shift, which is a key requirement for being able to multiplex the biosensor.

  DOI：

  10.1021/ja0483037
• 作为产物：
  描述：

  4-羟基-3-甲氧基苄醇 在 4-甲基苯磺酸吡啶 、 potassium carbonate 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 2-((4-(2-bromoethoxy)-3-methoxybenzyl)-oxy)tetrahydro-2H-pyran
  参考文献：
  名称：

  由固有手性远程单元控制的包围 Eu(III) 和 Tb(III) 配合物的圆偏振发光

  摘要：

  提出了一种基于分子笼的方法来获得具有圆偏振发光 (CPL) 活性的对映纯镧系元素配合物。通过使用 pyridine-2,6-dipicolinamide 配位基团对分子笼进行功能化，设计了半隐菌素内嵌配合物。利用远程环三萘嵌苯（CTV）单元的固有手性沿分子笼的连接体传播的能力，获得了具有受控手性的包封镧系配合物。通过这种方式，我们获得了 CPL 活性 Tb( III ) 和 Eu( III ) 笼，尽管手性 CTV 单元远离络合位点。这为在 CPL 应用中更广泛地使用对映纯共价笼开辟了道路。

  DOI：

  10.1039/d2nj02360a

文献信息

• A Straightforward Access to Cyclotriveratrylene Analogues with <i>C</i> ₁ Symmetry: Toward the Synthesis of Monofunctionalizable Cryptophanes
  作者：Gaëlle Milanole、Bo Gao、Emilie Mari、Patrick Berthault、Grégory Pieters、Bernard Rousseau

  DOI：10.1002/ejoc.201701353

  日期：2017.12.22

  A straightforward and practical access to various C1-symmetric cyclotriveratrylene derivatives from a monohalogenated cyclotriphenolene is described. This unique scaffold can also be used as a precursor for the rapid construction of monofunctionalizable cryptophane-based biosensors for hyperpolarized 129Xe MRI.

  描述了从单卤化环三苯酚获得各种 C1 对称环三戊四烯衍生物的直接而实用的途径。这种独特的支架还可以用作快速构建用于超极化 129Xe MRI 的基于单功能化隐甲的生物传感器的前体。
• Synthesis, Resolution, and Absolute Configuration of Chiral Tris(2-pyridylmethyl)amine-Based Hemicryptophane Molecular Cages
  作者：Dawei Zhang、Benjamin Bousquet、Jean-Christophe Mulatier、Delphine Pitrat、Marion Jean、Nicolas Vanthuyne、Laure Guy、Jean-Pierre Dutasta、Alexandre Martinez

  DOI：10.1021/acs.joc.7b00559

  日期：2017.6.16

  racemic mixture of each hemicryptophane host can be readily resolved by chiral HPLC, giving an easy access to the enantiopure molecular cages of which absolute configurations have been assigned by ECD spectroscopy. These new hemicryptophanes are available chemical platforms ready to use for various purposes due to the versatile metal complexation properties of the TPA unit. A Zn(II)@hemicryptophane

  报道了一种新的类半色氨酸笼的合成，表征和手性，该笼结合了环三藜芦烯单元和三（2-吡啶基甲基）胺（TPA）部分。改变这两个单元之间的接头可以改变空腔的尺寸和形状。合成简单有效，提供了克级的笼状化合物。每个半色氨酸宿主的外消旋混合物可通过手性HPLC轻松拆分，可轻松进入对映体纯分子笼，其绝对构型已通过ECD光谱确定。由于TPA装置具有多种金属络合特性，因此这些新的半色氨酸是可用于各种目的的化学平台。
• Improved hemicryptophane hosts for the stereoselective recognition of glucopyranosides
  作者：Aline Schmitt、Olivier Perraud、Elina Payet、Bastien Chatelet、Benjamin Bousquet、Marion Valls、Daniele Padula、Lorenzo Di Bari、Jean-Pierre Dutasta、Alexandre Martinez

  DOI：10.1039/c4ob00156g

  日期：——

  Slight changes in the chiral environment of enantiopure hemicryptophanes improve the stereoselective recognition of α and β anomers of glucopyranosides.

  对手性纯度半隐芳烃的手性环境进行轻微改变，可以提高对葡萄糖吡喃糖苷的α和β异构体的立体选择性识别。
• Synthesis of Cryptophane-223-Type Derivatives with Dual Functionalization
  作者：Orsola Baydoun、Nicolas De Rycke、Estelle Léonce、Céline Boutin、Patrick Berthault、Erwann Jeanneau、Thierry Brotin

  DOI：10.1021/acs.joc.9b01093

  日期：2019.7.19

  In this article, we present the synthesis of new cryptophane-type hosts capable of binding xenon in aqueous media and that may be useful for the development of xenon-based magnetic resonance imaging derivatives. The synthetic route proposed was chosen to facilitate both the introduction of water-solubilizing substituents and the functionalization of the host with a single arm showing recognition properties

  在本文中，我们介绍了能够在含水介质中结合氙的新型隐体型宿主的合成方法，这些宿主可能对基于氙的磁共振成像衍生物的开发很有用。选择所提出的合成途径以促进水溶性取代基的引入和具有单个臂的主体的功能化，该臂显示出构成两个关键步骤的识别特性。通过制备具有两种不同化学功能的新的cryptophane-223衍生物使之成为可能，这些衍生物可以在以后的阶段轻松进行修饰。因此，随后的反应允许设计一种能够结合锌或镍阳离子的新型隐蛋白宿主。通过量热滴定实验和超极化评估了该分子结合阳离子物质的能力。129 Xe NMR。讨论了这种方法的优缺点。
• Synthesis of cyclic peptide hemicryptophanes: enantioselective recognition of a chiral zwitterionic guest
  作者：James R. Cochrane、Aline Schmitt、Uta Wille、Craig A. Hutton

  DOI：10.1039/c3cc44784g

  日期：——

  The synthesis of the first members of a new class of cyclic peptide-containing hemicryptophanes is described. Synthesis was achieved through attachment of veratryl groups to the L-tyrosine side chains of a cyclic hexapeptide, c(YG)3, followed by intramolecular cyclodehydration to generate the CTV unit. The diastereomeric P- and M-hemicryptophanes were generated in a 2 : 1 ratio and were separated by

  描述了新型的含环肽的半色氨酸的第一类成员的合成。合成是通过将藜芦基团连接到环状六肽c（YG）3的L-酪氨酸侧链上，然后进行分子内环脱水来生成CTV单元而实现的。非对映异构体P-和M-半胱氨酸以2∶1的比例产生，并通过色谱法分离。通过与肉碱的络合研究半色氨酸的对映选择性结合特性。发现两种异构体对结合（R）-肉碱具有显着的选择性。