N-ethyl-N-(2-(prop-2-yn-1-yloxy)ethyl)aniline | 1001067-54-4

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-ethyl-N-(2-(prop-2-yn-1-yloxy)ethyl)aniline
• 英文别名: N-ethyl-N-(2-(prop-2-ynyloxy)ethyl)aniline
• CAS: 1001067-54-4
• 化学式: C₁₃H₁₇NO
• 分子量: 203.284
• InChiKey: SMAVUAPRGZELAX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.16
• 重原子数：
  15.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  12.47
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  N-ethyl-N-(2-(prop-2-yn-1-yloxy)ethyl)aniline 在 copper(ll) sulfate pentahydrate 、 sodium ascorbate 作用下， 以 二氯甲烷 、 水 、 正丁醇 、 苯 为溶剂， 反应 32.0h， 生成
  参考文献：
  名称：

  Water-soluble, deep-red fluorescent squaraine rotaxanes

  摘要：

  制备了八种深红色吸收/发射波长的荧光方酸轮烷，并评估了其化学稳定性和作为水溶性荧光示踪剂的适用性。最稳定的方酸轮烷具有四个大的塞子基团，位于包封方酸的两端，该结构类的两种成员有望作为高荧光示踪剂，在活体小鼠中具有迅速的肾清除率和极低的组织摄取。

  DOI：

  10.1039/c2ob06783h
• 作为产物：
  描述：

  N-乙基-N-羟乙基苯胺 、 3-氯丙炔 在 sodium hydroxide 、 四丁基硫酸氢铵 作用下， 以 苯 为溶剂， 反应 48.0h， 以86%的产率得到N-ethyl-N-(2-(prop-2-yn-1-yloxy)ethyl)aniline
  参考文献：
  名称：

  Self-Assembly of Fluorescent Inclusion Complexes in Competitive Media Including the Interior of Living Cells

  摘要：

  Anthracene-containing tetralactam macrocycles are prepared and found to have an extremely high affinity for squaraine dyes in chloroform (log K-a = 5.2). Simply mixing the two components produces highly fluorescent, near-infrared inclusion complexes in quantitative yield. An X-ray crystal structure shows the expected hydrogen bonding between the squaraine oxygens and the macrocycle amide NH residues, and a high degree of cofacial aromatic stacking. The kinetics and thermodynamics of the assembly process are very sensitive to small structural changes in the binding partners. For example, a macrocycle containing two isophthalamide units associates with the squaraine dye in chloroform 400 000 times faster than an analogous macrocycle containing two 2,6-dicarboxamidopyridine units. Squaraine encapsulation also occurs in highly competitive media such as mixed aqueous/organic solutions, vesicle membranes, and the organelles within living cells. The highly fluorescent inclusion complexes possess emergent properties; that is, as compared to the building blocks, the complexes have improved chemical stabilities, red-shifted absorption/emission maxima, and different cell localization propensities. These are useful properties for new classes of near-infrared fluorescent imaging probes.

  DOI：

  10.1021/ja075567v

文献信息

• Red Emitting Neutral Fluorescent Glycoconjugates for Membrane Optical Imaging
  作者：Sébastien Redon、Julien Massin、Sandrine Pouvreau、Evelien De Meulenaere、Koen Clays、Yves Queneau、Chantal Andraud、Agnès Girard-Egrot、Yann Bretonnière、Stéphane Chambert

  DOI：10.1021/bc500047r

  日期：2014.4.16

  A family of neutral fluorescent probes was developed, mimicking the overall structure of natural glycolipids in order to optimize their membrane affinity. Nonreducing commercially available di- or trisaccharidic structures were connected to a push–pull chromophore based on dicyanoisophorone electron-accepting group, which proved to fluoresce in the red region with a very large Stokes shift. This straightforward

  开发了一个中性荧光探针家族，模仿天然糖脂的整体结构，以优化其膜亲和力。非还原性市售的二糖或三糖结构与基于双氰基异佛尔酮电子接受基团的推挽发色团相连，事实证明该发色团在红色区域发出了很大的斯托克斯位移。这种简单明了的合成策略为一系列探针带来了结构变异，并对其光学，生物物理和生物学特性进行了研究。使用Langmuir单层平衡技术，在模型系统上评估了不同探针在膜中的插入特性。对肌肉细胞进行的共聚焦荧光显微镜检查显示完全不同的定位和加载效率，具体取决于探针的结构。与市售的ANEPPS（一种常用的膜成像染料家族）相比，最有效的探针显示出相似的亮度，但观察到更清晰的图案。根据这项研究，带有一个发色团，有限的碳水化合物部分大小和整体杆状形状的化合物可获得最佳结果。
• High-Frequency Mechanostimulation of Cell Adhesion
  作者：Laith F. Kadem、K. Grace Suana、Michelle Holz、Wei Wang、Hannes Westerhaus、Rainer Herges、Christine Selhuber-Unkel

  DOI：10.1002/anie.201609483

  日期：2017.1.2

  relief grating. We here use these oscillations to address single adhesion receptors. The effect of molecular oscillatory forces on cell adhesion has been analyzed using single‐cell force spectroscopy and gene expression studies. Our experiments demonstrate a reinforcement of cell adhesion as well as upregulated expression levels of adhesion‐associated genes as a result of the nanoscale “tickling” of integrins

  细胞粘附受到分子定义的蛋白质相互作用和机械力的调节，机械力可以激活粘附位点的动态重组。先前探索细胞粘附对力的反应的尝试仅限于施加涉及细胞骨架的机械刺激。相比之下，我们在这里通过推拉偶氮苯应用一种新的振荡类型的刺激。推拉偶氮苯在可见光照射下会产生高频分子振荡，这经常应用于聚合物表面浮雕光栅。我们在这里使用这些振荡来处理单个粘附受体。使用单细胞力谱和基因表达研究分析了分子振荡力对细胞粘附的影响。我们的实验证明，由于整合素的纳米级“痒痒”，细胞粘附得到加强，粘附相关基因的表达水平上调。这种新型机械刺激提供了前所未有的细胞机械传感分子控制。
• Using the Rotaxane Mechanical Bond to Enhance Chemical Reactivity
  作者：Jeffrey M. Baumes、Ivan Murgu、Allen Oliver、Bradley D. Smith

  DOI：10.1021/ol102132x

  日期：2010.11.5

  Rates of cycloreversion for squaraine rotaxane mono(endoperoxides) were enhanced by structural modifications that increased cross-component steric destabilization of the inward directed 9,10-anthracene endoperoxide group. The largest rate enhancements were obtained when the surrounding macrocycle contained two 2,6-pyridine dicarboxamide bridging units, which induced a cavity contraction effect. The precursor fluorescent, near-IR, squaraine rotaxanes are effectively photostable because the mono(endoperoxide) products, formed by reaction with photogenerated singlet oxygen, rapidly cyclorevert back to the original squaraine rotaxane.