2-氯-N-(2-甲基-4-喹啉基)乙酰胺 | 204587-07-5

• 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
• 中文名称: 2-氯-N-(2-甲基-4-喹啉基)乙酰胺
• 英文名称: chloro-N-(2-methyl-4-quinolyl)ethanamide
• 英文别名: 2-Chloro-N-(2-methylquinolin-4-yl)acetamide
• CAS: 204587-07-5
• 化学式: C₁₂H₁₁ClN₂O
• mdl: MFCD00264812
• 分子量: 234.685
• InChiKey: RTKWUKZLDHRJIY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.166
• 拓扑面积：
  42
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2933499090

反应信息

• 作为反应物：
  描述：

  2-氯-N-(2-甲基-4-喹啉基)乙酰胺 在 caesium carbonate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 14.83h， 生成 1,4,7-trisethyl(2-ethoxymethylphosphinate)-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 、 氯乙酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以60%的产率得到2-氯-N-(2-甲基-4-喹啉基)乙酰胺
  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

• Luminescent europium tetraazamacrocyclic complexes with wide range pH sensitivity
  作者：Thorfinnur Gunnlaugsson

  DOI：10.1039/a708342d

  日期：——

  The complexes [EuL1]3+ and [EuL2] function as luminescent pH sensors over an extended pH range; two distinguishable pH switching ranges are observed: the delayed europium emission is switched on in acidic solution, whereas the fluorescence emission spectra show a pronounced pH dependence only in alkaline media.

  [EuL1]3+和[EuL2]复合物可在较宽的 pH 值范围内发挥 pH 值发光传感器的功能；可观察到两个不同的 pH 值切换范围：延迟铕发射在酸性溶液中开启，而荧光发射光谱仅在碱性介质中显示出明显的 pH 值依赖性。
• 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。
• Substituted heterocyclic compounds
  申请人：——

  公开号：US20040152890A1

  公开（公告）日：2004-08-05

  Disclosed are novel heterocyclic derivatives, useful for the treatment of various disease states, in particular cardiovascular diseases such as atrial and ventricular arrhythmias, intermittent claudication, Prinzmetal's (variant) angina, stable and unstable angina, exercise induced angina, congestive heart disease, and myocardial infarction. The compounds are also useful in the treatment of diabetes.

  本发明涉及新型杂环衍生物，可用于治疗各种疾病状态，特别是心血管疾病，如心房和心室心律失常、间歇性跛行、普林兹梅特尔（变异型）心绞痛、稳定和不稳定性心绞痛、运动诱发性心绞痛、充血性心力衰竭和心肌梗塞。该化合物也可用于糖尿病的治疗。
• Substituted piperazine compounds and their use as fatty acid oxidation inhibitors
  申请人：CV THERAPEUTICS, INC.

  公开号：EP1806346A1

  公开（公告）日：2007-07-11

  Disclosed are novel heterocyclic derivatives, useful for the treatment of various disease states, in particular cardiovascular diseases such as atrial and ventricular arrhythmias, intermittent claudication, Prinzmetal's (variant) angina, stable and unstable angina, exercise induced angina, congestive heart disease, and myocardial infarction. The compounds are also useful in the treatment of diabetes.

  所公开的新型杂环衍生物可用于治疗各种疾病，尤其是心血管疾病，如房性和室性心律失常、间歇性跛行、普林兹梅塔尔（变异型）心绞痛、稳定型和不稳定型心绞痛、运动诱发心绞痛、充血性心脏病和心肌梗塞。这些化合物还可用于治疗糖尿病。
• New fatty acid oxidation inhibitors with increased potency lacking adverse metabolic and electrophysiological properties
  作者：Dmitry O. Koltun、Timothy A. Marquart、Kevin D. Shenk、Elfatih Elzein、Yuan Li、Marie Nguyen、Suresh Kerwar、Dewan Zeng、Nancy Chu、Daniel Soohoo、Jia Hao、Victoria Y. Maydanik、David A. Lustig、Khing-Jow Ng、Heather Fraser、Jeffery A. Zablocki

  DOI：10.1016/j.bmcl.2003.09.093

  日期：2004.1

  New inhibitors of palmitoylCoA oxidation were synthesized based on a structurally novel lead, CVT-3501 (1). Investigation of structure-activity relationships was conducted with respect to potency of inhibition of cardiac mitochondrial palmitoylCoA oxidation and metabolic stability. Potent and metabolically stable analogues 33, 42, and 43 were evaluated in vitro for cytochrome P450 inhibition and potentially adverse electrophysiological effects. Compound 33 was also found to have favorable pharmacokinetic properties in rat. (C) 2003 Elsevier Ltd. All rights reserved.