N-methyl-N-(2-(prop-2-yn-1-yloxy)ethyl)aniline | 1307897-45-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-methyl-N-(2-(prop-2-yn-1-yloxy)ethyl)aniline
• CAS: 1307897-45-5
• 化学式: C₁₂H₁₅NO
• 分子量: 189.257
• InChiKey: JWOLICXLFIIKRS-UHFFFAOYSA-N

物化性质

• 沸点：
  293.9±20.0 °C(predicted)
• 密度：
  1.030±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.77
• 重原子数：
  14.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 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-methyl-N-(2-(prop-2-yn-1-yloxy)ethyl)aniline 在 tetrafluoroboric acid 、 copper(I) sulfate pentahydrate 、 溶剂黄146 、 sodium ascorbate 、 sodium nitrite 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 31.0h， 生成 tetrabutylammonium 4-((4-((2-(methyl(4-((4-nitrophenyl)diazenyl)phenyl)amino)ethoxy)methyl)-1H-1,2,3-triazol-1-yl)methyl)benzenesulfonate
  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
• 作为产物：
  描述：

  N-甲基-N-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 72.0h， 生成 N-methyl-N-(2-(prop-2-yn-1-yloxy)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

• Time-lapse imaging of cell death in cell culture and whole living organisms using turn-on deep-red fluorescent probes
  作者：Tia S. Jarvis、Felicia M. Roland、Kyle M. Dubiak、Paul W. Huber、Bradley D. Smith

  DOI：10.1039/c8tb01495g

  日期：——

  regression and apoptosis during growth and maturation. These new fluorescent probes are likely to be useful for time-resolved, non-invasive in vivo imaging of cell death process in range of living organisms. From a broader perspective, it should be possible to utilize the negative solvatochromism exhibited by benzothiazolium squaraine dyes for development of various “turn-on” deep-red fluorescent probes

  细胞死亡是发育生物学的核心过程，也是疾病状态和治疗效果的重要指标。描述了两种相关的荧光探针，它们是一种或两种锌二吡啶胺 (ZnDPA) 配位络合物与附加的溶剂化显色苯并噻唑鎓方酸染料的分子缀合物。这些探针旨在针对暴露在死亡和垂死细胞表面的阴离子磷脂磷脂酰丝氨酸（PS）。以脂质体和红细胞血影为模型的一系列光谱和显微镜研究表明，具有两个 ZnDPA 靶向单元的探针比具有一个 ZnDPA 的探针产生更高的亲和力、更强的荧光“开启”效应和更好的图像对比度。两种荧光探针都可以对培养物中的哺乳动物细胞死亡进行“免清洗”延时显微成像。带有两个 ZnDPA 单元的探针用于对非洲爪蟾（青蛙）胚胎发育过程中的细胞死亡进行非侵入性延时成像。体内荧光显微照片显示，探针在胚胎尾部、头部和脊柱区域内积累，这些区域在生长和成熟过程中正在经历退化和凋亡。这些新的荧光探针可能可用于对各种活体生物体的细胞死亡过程进行时间分辨
• Macrocycle threading using solvatochromic squaraine dyes
  作者：Tia S. Jarvis、Bradley D. Smith

  DOI：10.1080/10610278.2019.1568433

  日期：2019.3.4

  Non-covalent assembly is an attractive way to fabricate deep-red fluorescent probes for biological imaging. Four new solvatochromic squaraine dyes with unsymmetric structures are prepared and shown to exhibit macrocyclic encapsulation by tetralactam macrocycle in chloroform solvent or in water. Macrocycle threading in chloroform produces a relatively small 20 nm red-shift in absorption wavelength. In contrast, macrocycle threading in water produces similar to 80 nm red-shift in absorption wavelength, indicating a large change in polarity surrounding the solvatochromic squaraine as it transfers from bulk water solution to the relatively non-polar macrocycle interior. The large red-shift in absorption maxima translates into a very large 70-fold enhancement of squaraine fluorescence. Macrocycle threading in water by two homologous squaraines was studied and there was a large difference in threading kinetics. Macrocycle threading by a squaraine with an N-methyl substituent at the end of the structure was 5 million times faster than threading by a squaraine with an N-propyl substituent.[GRAPHICS].
• Internal and External Stereoisomers of Squaraine Rotaxane Endoperoxide: Synthesis, Chemical Differences, and Structural Revision
  作者：Carleton G. Collins、Joshua M. Lee、Allen G. Oliver、Olaf Wiest、Bradley D. Smith

  DOI：10.1021/jo402564k

  日期：2014.2.7

  Photooxygenation of permanently interlocked squaraine rotaxanes with anthracene-containing macrocydes produces the corresponding squaraine rotaxane endoperoxides (SREPs) quantitatively. SREPs are stored at low temperature, and upon warming, they undergo clean cycloreversion, releasing singlet oxygen and emitting light. The structural elucidation in 2010 assigned the structure as the SREP-int stereoisomer, with the endoperoxide unit directed inside the macrocycle cavity. New experimental and computational evidence reported here proves that the initial, kinetic photooxygenation product is the less stable SREP-ext stereoisomer with the endoperoxide unit directed outside the macrocycle. The photophysical properties and subsequent reactivity of mechanically strained SREP-ext depend on the size of the end groups of the encapsulated squaraine dye. If the end groups are sufficiently large to prevent dissociation of the interlocked components, the strained SREP-ext stereoisomer undergoes clean, thermal cycloreversion. However, smaller squaraine end groups allow transient dissociation, resulting in a pseudorotaxane dissociation/association process that produces SREP-int as the thermodynamic stereoisomer that does not cyclorevert. The large difference in endoperoxide reactivity for the two SREP stereoisomers illustrates the power of the mechanical bond to induce cross-component steric strain and selective enhancement of a specific reaction pathway. The new insight enabled synthetic development of triptycene-containing squaraine rotaxanes with high fluorescence quantum yields and large Stokes shifts.