N,N-bis(2-(prop-2-ynyloxy)ethyl)aniline | 1202493-52-4

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N,N-bis(2-(prop-2-ynyloxy)ethyl)aniline
• CAS: 1202493-52-4
• 化学式: C₁₆H₁₉NO₂
• 分子量: 257.332
• InChiKey: JPXADURFQKOZIS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.79
• 重原子数：
  19.0
• 可旋转键数：
  9.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  21.7
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  N,N-bis(2-(prop-2-ynyloxy)ethyl)aniline 在 三氯氧磷 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 8.5h， 生成 10-(4-(bis(2-(prop-2-yn-1-yloxy)ethyl)amino)phenyl)-5,5-difluoro-1,3,7,9-tetramethyl-5H-4l4,5l4-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinine-2-carbaldehyde
  参考文献：
  名称：

  点击反应制备的壳聚糖-二甲基吡啶大分子荧光探针用于高灵敏度和选择性识别2,4-二硝基苯肼

  摘要：

  硝基化合物广泛用于现代工业。其中，2, 4-二硝基苯肼（DNH）危害极大。开发DNH检测方法具有重要意义。在这项工作中，壳聚糖用作底物材料，氟硼二吡咯（BODIPY）用作荧光团。通过引入BODIPY单元，壳聚糖被赋予了荧光传感能力。首先，合成了具有炔基 (C C) 的BODIPY 衍生物（NO-3和BO-1 ） 。其次，获得了带有醛基（-CHO）的小分子NO-4和BO-2 。最后，壳聚糖上的-NH 2基团发生了点击反应（-NH 2 /CC)和席夫碱形成反应(-NH 2 /-CHO)形成三个聚合物探针C1、C2和C3。在点击反应中形成的C C 可以与 DNH 相互作用，可以作为 DNH 的识别位点。这些壳聚糖探针具有良好的热稳定性，可以选择性地识别DNH，具有明显的荧光猝灭效应，肉眼可见。DNH是典型的缺电子化合物，聚合物荧光探针含有富电子基团，这使得两种物质更容易结合并引起荧光变化。C1为

  DOI：

  10.1039/d2nj03923k
• 作为产物：
  描述：

  N,N-二羟乙基苯胺 、 3-溴丙炔 在 potassium hydroxide 作用下， 以 二甲基亚砜 为溶剂， 反应 120.0h， 生成 N,N-bis(2-(prop-2-ynyloxy)ethyl)aniline
  参考文献：
  名称：

  Novel Synthesis of Hydrophilic Dipolar Chromophores using Dendronized Sulfonates

  摘要：

  通过点击化学引入树枝状磺酸盐阴离子，合成了一系列亲水性发色团。具有多个磺酸基团的树枝状结构增强了附着发色团的亲水性。点击三唑形成将发色团与亲水基团连接。三氯乙基磺酸中性盐具有多种特性，如易于引入、耐化学性以分离或储存，以及方便转化为亲水性阴离子。锌和羟基介导的中性磺酸盐上的三氯乙基断裂，产生水溶性磺酸盐阴离子。在不同反离子和不同pH介质中检验了溶解度，因此随着附着的磺酸离子数量的增加而提高。两种亲水性发色团，即芪衍生和偶氮苯衍生偶极结构，分别在质子溶剂中表现出明显的负向和正向溶剂化变色效应。

  DOI：

  10.5012/bkcs.2011.32.2.664

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。
• Water-soluble, deep-red fluorescent squaraine rotaxanes
  作者：Erin L. Cole、Easwaran Arunkumar、Shuzhang Xiao、Bryan A. Smith、Bradley D. Smith

  DOI：10.1039/c2ob06783h

  日期：——

  Eight fluorescent squaraine rotaxanes with deep-red absorption/emission wavelengths were prepared and assessed for chemical stability and suitability as water-soluble, fluorescent tracers. The most stable squaraine rotaxanes have four large stopper groups attached to the ends of the encapsulated squaraine, and two members of this structural class have promise as highly fluorescent tracers with rapid renal clearance and very low tissue uptake in living mice.

  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。
• Straightforward synthesis of bioconjugatable azo dyes. Part 1: Black Hole Quencher-1 (BHQ-1) scaffold
  作者：Arnaud Chevalier、Pierre-Yves Renard、Anthony Romieu

  DOI：10.1016/j.tetlet.2014.10.053

  日期：2014.12

  Azo dyes are currently used to quench the fluorescence of energy donors in bioassays through Forster resonance energy transfer (FRET) phenomenon. Common examples of such dark quenchers are DABCYL and the three members of Black Hole Quencher (R) (BHQ) family. Yet, only carboxylic acid and phosphoramidite derivatives of such azo dyes are presently commercially available. This Letter presents a straightforward synthesis method to novel bioconjugatable quenchers derived from BHQ-1 scaffold and equipped with a reactive group being either azido, terminal alkyne, or maleimide. The potential utility of the 'clickable' azido and thiol-reactive derivatives was notably demonstrated through the preparation of the first water-soluble BHQ-1 dye and a FRET-based probe suitable for the detection of urokinase-type plasminogen activator (uPA), a key protease in cancer invasion and metastasis, respectively. (C) 2014 Elsevier Ltd. All rights reserved.
• Dye-incorporated water-soluble polymer via click triazole formation
  作者：Byungkwon Jang、Sung Yoon Kim、Jung Yun Do

  DOI：10.1016/j.dyepig.2012.01.012

  日期：2012.8

  A click triazole-polymerization is proposed for the synthesis of a water-soluble polymer dye. 4,4'-Diazidostilbene-2,2'-disulfonate (DASS) sodium salt reacted with a diacetylenic derivative of para-methyl red (PMR) in water, which was catalyzed by copper (I) ion or accelerated under ultrasound irradiation. DASS formed a soluble polymer with a carboxylate salt of PMR showing a water solubility of 120 g/100 mL but it generated an insoluble polymer with an alkyl ammonium salt. The prepared polymeric dye underwent color transition at pH 5-6, which is higher than that of PMR and similar to that of ortho-methyl red (OMR). The quinonoid canonical structure of PMR generated a purple water solution and was dominant in the polymer solution at pH below 5. Intra-molecular hydrogen bonding between the triazoles and azo nitrogens was presumed to have induced the formation of the quinonoid structure. The color change of the polymer was reproducible during successive up/down pH cycles. (C) 2012 Elsevier Ltd. All rights reserved.
• Efficient Synthesis of Fluorescent Squaraine Rotaxane Dendrimers
  作者：Shuzhang Xiao、Na Fu、Kaitlin Peckham、Bradley D. Smith

  DOI：10.1021/ol902546m

  日期：2010.1.1

  A squaraine rotaxane scaffold with four alkyne groups is readily converted into a range of dendritic architectures using high-yielding copper-catalyzed alkyne azide cycloaddition (CuAAC) chemistry. A convergent synthesis approach is more efficient than a divergent pathway. Dendritic squaraine rotaxanes with peripheral amine groups can be further functionalized to produce multivalent deep-red fluorescent derivatives that exhibit high brightness and outstanding chemical stability in biological solution. The surface groups on these functionalized fluorescent dendrimers include guanidinium, mannose, and phosphatidylcholine.