2,6-bis(propargyloxy)naphthalene | 20009-43-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2,6-bis(propargyloxy)naphthalene
• 英文别名: 2,6-bis-prop-2-ynyloxynaphthalene；2,6-Bis(prop-2-ynyloxy)naphthalene；2,6-bis(prop-2-ynoxy)naphthalene
• CAS: 20009-43-2
• 化学式: C₁₆H₁₂O₂
• 分子量: 236.27
• InChiKey: KHDYTWZCIPSMNZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,6-bis(propargyloxy)naphthalene 在 氢气 、 sodium cyanoborohydride 、 三氯氧磷 作用下， 反应 1.25h， 生成 1-<(benzylamino)methyl>-2,6-bis(1'-propoxy)naphthalene
  参考文献：
  名称：

  Preparation and characterization of 1,8,19,26-tetraoxa[8.8](2,6)naphthalenophane-3,5,21,23-tetrayne and related donut-shaped cyclophanes

  摘要：

  DOI：

  10.1021/jo00322a018
• 作为产物：
  描述：

  2,6-萘二酚 、 3-溴丙炔 以87%的产率得到2,6-bis(propargyloxy)naphthalene
  参考文献：
  名称：

  叠氮化物官能化的PAMAM树突的合成及其在PAMAM类树状聚合物合成中的应用

  摘要：

  第一次，以叠氮基丙胺为叠氮化物焦点，进行叠氮化物官能化的PAMAM树突的发散性合成，以及通过带有拨号键核心的点击化学，聚合合成包含1,2,3-三唑环作为连接体的对称PAMAM状树状大分子的方法。描述。

  DOI：

  10.1016/j.tetlet.2006.02.081

文献信息

• Synthesis of bivalent lactosides and their activity as sensors for differences between lectins in inter- and intrafamily comparisons
  作者：Sabine André、Dilip V. Jarikote、Dandan Yan、Lisa Vincenz、Guan-Nan Wang、Herbert Kaltner、Paul V. Murphy、Hans-Joachim Gabius

  DOI：10.1016/j.bmcl.2011.11.010

  日期：2012.1

  adhesion/growth-regulatory galectins from one organism (chicken) to a glycoprotein or to cell surfaces was systematically evaluated. Differential sensitivities were detected between plant and animal lectins and also between distinct galectin forms within the chicken series. Two of the bivalent probes can be considered as sensors for interlectin differences. Most pronounced were the selectivities of N-glycosyl 1

  九种二价乳糖苷（基于二三唑，二酰胺，糖环庚烷和糖环庚烷的无环类似物）和一种单价乳糖基三唑的合成促进了植物/动物凝集素对这种配体展示的敏感性的评估。在增加生物相关性的两种测定中确定了化合物的抑制能力。这些是固相和细胞结合设置。因此，系统地评估了化合物抑制两种植物凝集素和来自一个生物体（鸡）的整套粘附/生长调节半乳糖凝集素与糖蛋白或细胞表面结合的能力。在动植物凝集素之间以及鸡系列中不同的半乳凝素形式之间检测到不同的敏感性。二价探针中的两个可以看作是互凝素差异的传感器。最明显的是嵌合型半乳凝素的N-糖基1,2,3-三唑衍生物及其蛋白水解截短形式。
• Biomimetic Recognition and Optical Sensing of Carboxylic Acids in Water by Using a Buried Salt Bridge and the Hydrophobic Effect
  作者：Xuan Huang、Xiaoping Wang、Mao Quan、Huan Yao、Hua Ke、Wei Jiang

  DOI：10.1002/anie.202012467

  日期：2021.1.25

  protein structures but are rarely used in synthetic systems for molecular recognition in water. By mimicking the binding pocket of bioreceptors, we designed and synthesized a pair of endo‐functionalized macrocyclic hosts with secondary ammonium groups in a hydrophobic cavity. We found that these macrocycles are able to selectively recognize carboxylic acids in water through salt bridges and the hydrophobic

  埋入式盐桥广泛存在于蛋白质结构中，但很少用于水分子识别的合成系统中。通过模仿生物受体的结合口袋，我们设计并合成了一对在疏水腔中具有仲铵基团的内官能化大环宿主。我们发现这些大环化合物能够通过盐桥和疏水作用选择性识别水中的羧酸。此外，已证明这些大环受体可用于手性羧酸的基于圆二色性的光学手性传感和苯基丙酮酸（一种苯丙酮尿症的生物标志物）的荧光传感。这项研究表明，埋入式盐桥可以被内窥镜有效地利用官能化的大环宿主，可在水中进行分子识别，因为对极性非共价相互作用的溶剂筛选很高。
• Venugopalan, Bindumadhavan; Balasubramanian,Kalpattu Kuppuswamy, Heterocycles, 1985, vol. 23, # 1, p. 81 - 92
  作者：Venugopalan, Bindumadhavan、Balasubramanian,Kalpattu Kuppuswamy

  DOI：——

  日期：——
• Convergent synthesis of PAMAM dendrimers using click chemistry of azide-functionalized PAMAM dendrons
  作者：Jae Wook Lee、Jung Hwan Kim、Byung-Ku Kim、Ji Hyeon Kim、Won Suk Shin、Sung-Ho Jin

  DOI：10.1016/j.tet.2006.07.030

  日期：2006.9

  Azide-functionalized PAMAM dendrons containing an azidopropylamine focal point were synthesized by the divergent method and applied for the construction of symmetric PAMAM-like dendrimers containing 1,2,3-triazole rings as connectors via stitching with two different multi-terminal alkynes. The stitching method was based on the click chemistry protocol, i.e., the copper-catalyzed cycloaddition reaction between an alkyne and an azide. (c) 2006 Elsevier Ltd. All rights reserved.
• Synthesis of bivalent glycoclusters containing GlcNAc as hexasaccharide mimetics. Bactericidal activity against Helicobacter pylori
  作者：Dandan Yan、Julie Naughton、Marguerite Clyne、Paul V. Murphy

  DOI：10.1016/j.carres.2012.07.011

  日期：2012.10

  The Cu(I) catalysed cycloaddition reaction of azides and alkynes has been used to generate a series of divalent GlcNAc clusters with both alpha and beta configurations. These glycoclusters can be considered as potential mimetics of an anti Helicobacter pylori hexasaccharide as they present two GlcNAc residues grafted onto a core scaffold. Two bivalent compounds based on alpha-O-GlcNAc were identified that selectively reduced the viability of H. pylori. These compounds showed activity towards different strains of H. pylori (Pu4 vs P12). The activity of the oligosaccharide mimetics is speculated to be due to the GlcNAc residues being able to adopt spatial arrangements accessible to the anti H. pylori hexasaccharide which may be important for activity. (C) 2012 Elsevier Ltd. All rights reserved.