1-[N-(2-methyl-4-quinolyl)carbamoylmethyl]-1,4,7,10-tetraazacyclododecane | 392686-58-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1-[N-(2-methyl-4-quinolyl)carbamoylmethyl]-1,4,7,10-tetraazacyclododecane
• 英文别名: N-(2-methyl-quinolin-4-yl)-2-(1,4,7,10-tetraaza-cyclododec-1-yl)acetamide；N-(2-methylquinolin-4-yl)-2-(1,4,7,10-tetrazacyclododec-1-yl)acetamide
• CAS: 392686-58-7
• 化学式: C₂₀H₃₀N₆O
• 分子量: 370.498
• InChiKey: IVXDEKVDGIZWPS-UHFFFAOYSA-N

物化性质

• 沸点：
  616.4±55.0 °C(Predicted)
• 密度：
  1.108±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  81.3
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-[N-(2-methyl-4-quinolyl)carbamoylmethyl]-1,4,7,10-tetraazacyclododecane 在 氘氧化钾 、 重水 作用下， 以 四氢呋喃 为溶剂， 反应 24.33h， 生成 1,4,7-tris[ethyl(2-methylphosphinic acid)]-10-[N-(2-methyl-4-quinolyl)carbamoylmethyl]-1,4,7,10-tetraazacyclododecane
  参考文献：
  名称：

  Lanthanide Macrocyclic Quinolyl Conjugates as Luminescent Molecular-Level Devices

  摘要：

  The Eu(III) tetraazamacrocyclic complexes [Eu.1] and [Eu.2], and the Tb(III) and Yb(III) complexes [Tb.1] and [Yb.2], have been synthesized as luminescent molecular-level devices. The Eu complexes exhibit unique dual pH switching behavior in water under ambient conditions. The delayed Eu emission is reversibly switched on in acid, with an enhancement factor of several hundred for [Eu-1]. These observations are consistent with the protonation of the quinoline aryl nitrogen moiety (pK(a) approximate to 5.9 for [Eu.1]). The fluorescence emission spectra of these complexes are unaffected by acid, but pronounced changes occur in alkaline solution due to the deprotonation of the aryl amide nitrogen (pK(a) approximate to 9.4 for [Eu.1]). [Tb.1] shows a more intriguing pH dependence; Tb emission is switched "on" only in the presence of HI and in the absence of molecular oxygen, whereas the fluorescence emission properties are similar to those observed with [Eu-1]. This behavior can be conveniently described as a molecular-level logic gate, corresponding to a two-input INHIBIT function, A boolean AND B'. The analogous [Yb.2] complex shows no such pH or O-2 dependence.

  DOI：

  10.1021/ja004316i
• 作为产物：
  描述：

  4-氨基喹哪啶 在 caesium carbonate 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.5h， 生成 1-[N-(2-methyl-4-quinolyl)carbamoylmethyl]-1,4,7,10-tetraazacyclododecane
  参考文献：
  名称：

  Lanthanide Macrocyclic Quinolyl Conjugates as Luminescent Molecular-Level Devices

  摘要：

  The Eu(III) tetraazamacrocyclic complexes [Eu.1] and [Eu.2], and the Tb(III) and Yb(III) complexes [Tb.1] and [Yb.2], have been synthesized as luminescent molecular-level devices. The Eu complexes exhibit unique dual pH switching behavior in water under ambient conditions. The delayed Eu emission is reversibly switched on in acid, with an enhancement factor of several hundred for [Eu-1]. These observations are consistent with the protonation of the quinoline aryl nitrogen moiety (pK(a) approximate to 5.9 for [Eu.1]). The fluorescence emission spectra of these complexes are unaffected by acid, but pronounced changes occur in alkaline solution due to the deprotonation of the aryl amide nitrogen (pK(a) approximate to 9.4 for [Eu.1]). [Tb.1] shows a more intriguing pH dependence; Tb emission is switched "on" only in the presence of HI and in the absence of molecular oxygen, whereas the fluorescence emission properties are similar to those observed with [Eu-1]. This behavior can be conveniently described as a molecular-level logic gate, corresponding to a two-input INHIBIT function, A boolean AND B'. The analogous [Yb.2] complex shows no such pH or O-2 dependence.

  DOI：

  10.1021/ja004316i

文献信息

• Selective mono N-alkylations of cyclen in one step syntheses
  作者：Julien Massue、Sally E. Plush、Célia S. Bonnet、Doireann A. Moore、Thorfinnur Gunnlaugsson

  DOI：10.1016/j.tetlet.2007.09.022

  日期：2007.11

  cyclen (1,4,7,10-tetraazacyclododecane) using a range of functionalized alkyl halides. This ‘easy to use’ synthesis gives rise to mono-derivatives of cyclen from various alkyl halides or, when using alkyl dihalides, bis-cyclen derivatives, where the alkyl group links two cyclen macrocycles together. While the reaction conditions require the use of 1:4 stoichiometry (alkyl halide:cyclen), any unreacted

  在这封信中，我们描述了使用一系列官能化的烷基卤化物进行的环己酮（1,4,7,10-四氮杂环十二烷）的选择性一步单N-烷基化。这种“易于使用”的合成方法产生了由各种卤代烷形成的环素单衍生物，或者，当使用烷基二卤化物时，产生了双环素衍生物，其中烷基将两个环素大环连接在一起。虽然反应条件要求使用化学计量比为1：4（卤代烷：环烷烃），但任何未反应的环糊精都可以通过水萃取法回收并成功地重复使用。发现该方法是非常通用的，特别适合于带有受保护的硫醇基团以及α-氯酰胺衍生的生色团的循环目标。这种细胞周期垂体生色团被用作镧系元素发光探针和传感器的触角。
• Lanthanide macrocyclic quinolyl conjugates as luminescent molecular switches and logic gate functions using HO− and O2 as inputs
  作者：Célia S. Bonnet、Thorfinnur Gunnlaugsson

  DOI：10.1039/b820372e

  日期：——

  The design and synthesis of 1Tb, a Tb(III) quinoline–cyclen based complex, are described. The results from the photophysical investigation of 1Tb are compared with the results observed from its Eu(III) analogue, 1Eu. The Tb(III) emission of 1Tb was found to be highly pH dependent, being reversibly switched “off–on–off”, with maximum emission intensities observed within the physiological pH range, contrary

  设计和合成了1Tb（一种基于Tb（III）喹啉-环素的配合物）。将1Tb的光物理研究结果与从其Eu（III）类似物1Eu观察到的结果进行比较。发现1Tb的Tb（III）发射高度依赖于pH，可逆地“关闭-打开-关闭”切换，在生理pH范围内观察到最大发射强度，这与Eu（III）类似物观察到的相反。此外，Tb（III还发现发射对分子氧浓度敏感。通过使用化学计量的两种配合物，镧系元素的Eu / Tb排放总量（描述为输出）随pH和O 2的变化（作为离子/分子输入）的变化可用于这些分析物的比例感测。 。此外，输出还可以用分子逻辑门术语来描述，其中可以用布尔代数来描述三种不同发射波长的发射，这与NAND，NOR和NOT逻辑门功能相对应。