3-chloro-N-(quinolin-8-yl)propanamide | 858420-25-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 3-chloro-N-(quinolin-8-yl)propanamide
• 英文别名: 3-chloro-N-quinolin-8-ylpropanamide
• CAS: 858420-25-4
• 化学式: C₁₂H₁₁ClN₂O
• 分子量: 234.685
• InChiKey: AYBJYZRADLYYEI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  42
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-chloro-N-(quinolin-8-yl)propanamide 、 二甲基吡啶胺 在 N,N-二异丙基乙胺 、 sodium iodide 作用下， 以 乙腈 为溶剂， 反应 10.0h， 以89.6%的产率得到3-dipicolylamine-N-(quinoline-8-yl)propanamide
  参考文献：
  名称：

  Zinc selective chemosensors based on the flexible dipicolylamine and quinoline

  摘要：

  Zinc sensor molecules containing quinoline have been synthesized, which show fluorescence in the presence of Zn2+. The nitrogen in quinoline is critical to fluorescence and fluorescence enhancement is promoted by deprotonating the sensor's amide. One of the sensors is highly selective for Zn2+ over Cd2+ and other cations such as Hg2+, Fe2+, Mn2+ and Ca2+. This selectivity can be attributed to the increased absorption of the sensor in the presence of Zn2+ and the strong binding of Zn2+. Structural studies, including X-ray and NMR, show the ability of dipicolylamine (DPA) to bind in facial and meridional manners to Zn2+. Crystal structures of different compounds show Zn2+ coordinating to three, four, and five nitrogens from the compounds. They also indicate that the selectivity of DPA containing compounds towards Zn2+ may originate from Zn2+ being stable in different coordination environments. (C) 2012 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.ica.2012.09.009
• 作为产物：
  描述：

  3-hydroxy-N-(quinolin-8-yl)propanamide 在 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以94%的产率得到3-chloro-N-(quinolin-8-yl)propanamide
  参考文献：
  名称：

  Unactivated C(sp³)–H hydroxylation through palladium catalysis with H₂O as the oxygen source

  摘要：

  一种新颖的钯催化的未活化脂肪族C(sp3)-H键的羟基化反应成功开发。与传统方法不同，水在反应中作为羟基源。该反应展示了广泛的官能团容忍性。

  DOI：

  10.1039/c5cc04952k

文献信息

• Cu-Catalyzed Alkynylation of Unactivated C(sp³)–X Bonds with Terminal Alkynes through Directing Strategy
  作者：Fei-Xian Luo、Xing Xu、Ding Wang、Zhi-Chao Cao、Yun-Fei Zhang、Zhang-Jie Shi

  DOI：10.1021/acs.orglett.6b00289

  日期：2016.5.6

  and concise protocol for Cu-catalyzed cross-coupling of unactivated alkyl halides/peusudohalides with terminal alkynes to afford internal alkynes with the assistance of various amides as directing groups. Different alkyl halides/pseudohalides exhibited excellent reactivities, and the inactivated alkyl chlorides and sulfonates showed better reactivity than bromides/iodides. This is the first successful

  在这封信中，我们报告了一种有效而简洁的方案，用于铜催化未活化烷基卤化物/伪卤化物与末端炔烃的交叉偶联，从而借助各种酰胺作为导向基团提供内部炔烃。不同的烷基卤化物/假卤化物显示出优异的反应性，而灭活的烷基氯化物和磺酸盐显示出比溴化物/碘化物更好的反应性。这是在没有任何添加剂的情况下直接将烷基氯化物和磺酸盐与末端炔烃进行交叉偶联的第一个成功实例。发现Cu催化剂比其他过渡金属催化剂更有效。对于末端炔烃，该反应还显示出较宽的底物范围。
• A highly selective fluorescent chemosensor based on a quinoline derivative for zinc ions in pure water
  作者：Ye Won Choi、Jae Jun Lee、Cheal Kim

  DOI：10.1039/c5ra09954d

  日期：——

  water-soluble fluorescent ‘turn-on’ chemosensor for zinc ions. In 100% aqueous buffer solution, sensor 1 displayed a selective fluorescence enhancement (317-fold) at 536 nm with Zn2+. The detection limit (4.48 μM) of 1 for Zn2+ was far below the WHO guideline (76 μM) in drinking water. Importantly, sensor 1 could be used to detect and quantify Zn2+ in water samples. Moreover, the sensing ability of 1 for Zn2+

  合成了一种新的基于喹啉的简单受体1，作为水溶性荧光锌离子“开启”化学传感器。在100％的缓冲水溶液中，传感器1在536 nm处显示Zn 2+的选择性荧光增强（317倍）。的检测限（4.48μM）1为锌2+远低于在饮用水WHO指南（76μM）。重要的是，传感器1可用于检测和定量水样品中的Zn 2+。此外，理论计算支持了1对Zn 2+的感测能力。因此，该传感器1有能力成为监测含水样品中Zn 2+浓度的实用系统。
• A highly selective CHEF-type chemosensor for monitoring Zn²⁺ in aqueous solution and living cells
  作者：Jae Jun Lee、Seul Ah Lee、Hyun Kim、LeTuyen Nguyen、Insup Noh、Cheal Kim

  DOI：10.1039/c5ra05080d

  日期：——

  A new quinolone-based chemosensor was synthesized and successfully applied to quantify and image Zn²⁺ in water samples and living cells.

  一种基于喹诺酮的化学传感器被合成并成功应用于水样和活细胞中锌离子的定量和成像。
• Zinc sensors with lower binding affinities for cellular imaging
  作者：Jin Hoon Kim、In Hong Hwang、Seung Pyo Jang、Juhye Kang、Sumi Kim、Insup Noh、Youngmee Kim、Cheal Kim、Roger G. Harrison

  DOI：10.1039/c3dt33024a

  日期：——

  Zinc sensors based on 2,3-dipicolylamine (DPA) and quinoline have been synthesized. They fluoresced in the presence of Zn2+ and remained fluorescent when other metal ions were present. Fluorescence enhancement of the sensors was not seen for most other metal ions. In vitro studies with fibroblasts showed fluorescence when sensor and Zn2+ were present. As seen by single crystal X-ray analysis, four nitrogens from the sensor bind to Zn2+. These new sensors have lower binding constants than the pentadentate sensors based on 2,2-DPA.

  我们合成了基于 2,3-二二甲胺（DPA）和喹啉的锌传感器。它们在 Zn2+ 存在时发出荧光，而在其他金属离子存在时则保持荧光。对于大多数其他金属离子，传感器的荧光增强效果并不明显。对成纤维细胞进行的体外研究显示，当传感器和 Zn2+ 同时存在时，成纤维细胞会发出荧光。单晶 X 射线分析显示，传感器的四个硝基与 Zn2+ 结合。这些新型传感器的结合常数低于基于 2,2-DPA 的五价传感器。
• A Turn-on Fluorescent Chemosensor for Zn2+ Based on Quinoline in Aqueous Media
  作者：Yong Sung Kim、Jae Jun Lee、Sun Young Lee、Pan-Gi Kim、Cheal Kim

  DOI：10.1007/s10895-016-1771-x

  日期：2016.5

  “off-on fluorescence type” chemosensor 1 3-((2-(dimethylamino)ethyl)amino)-N-(quinolin-8-yl)propanamide has been synthesized for Zn2+. The receptor 1 comprises the quinoline moiety as fluorophore and the N,N′-dimethylethane-1,2-diamine as a binding site. 1 showed a remarkable fluorescence enhancement in the presence of Zn2+ in aqueous solution. Importantly, the chemosensor 1 could be used to detect

  Zn 2+已合成了一种简单的“关闭荧光型”化学传感器1 3-（（2-（二甲基氨基）乙基）氨基）-N-（喹啉-8-基）丙酰胺。受体1包括喹啉部分为荧光团和N，N- ' -二甲基环己烷-1,2-二胺作为结合位点。图1在水溶液中存在Zn 2+时显示出显着的荧光增强。重要的是，化学传感器1可用于检测和定量水样品中的Zn 2+。特别是，该化学传感器可以清楚地区分Zn 2+和Cd 2+。1与Zn的结合特性通过UV-vis，荧光，电喷雾电离质谱和1 H NMR滴定研究了2+离子。