2-(pyridine-2-ylethynyl)quinoline | 1229283-66-2

• 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: 2-(pyridine-2-ylethynyl)quinoline
• 英文别名: 2-(pyridin-2-ylethynyl)quinoline；2-(2-pyridylethynyl)quinoline；2-(2-Pyridin-2-ylethynyl)quinoline
• CAS: 1229283-66-2
• 化学式: C₁₆H₁₀N₂
• 分子量: 230.269
• InChiKey: IRXAEZFKUGBIIX-UHFFFAOYSA-N

物化性质

• 熔点：
  94-97 °C
• 沸点：
  435.9±20.0 °C(predicted)
• 密度：
  1.23±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  戊-3-炔基三氟甲磺酸酯 、 2-(pyridine-2-ylethynyl)quinoline 以 甲苯 为溶剂， 反应 25.0h， 以67%的产率得到1-(pent-3-ynyl)-2-(quinolin-2-ylethynyl)pyridinium trifluoromethanesulfonate
  参考文献：
  名称：

  Highly modular assembly of cationic helical scaffolds: rapid synthesis of diverse helquats via differential quaternization

  摘要：

  A protocol for rapid and highly modular assembly of a diverse set of helquats is described. From a common bis-isoquinoline precursor, two successive distinct pyridine-type nitrogen quaternizations followed by rhodium-catalyzed [2+2+2] cycloaddition afford non-symmetric [7]helquats. This route allows for straightforward molecular editing of cationic helical skeletons as exemplified by the synthesis of 15 different [5]-, [6]-, and [7]helquats. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.03.007
• 作为产物：
  描述：

  2-乙炔基吡啶 、 2-氯喹啉 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 反应 21.0h， 以70%的产率得到2-(pyridine-2-ylethynyl)quinoline
  参考文献：
  名称：

  Highly modular assembly of cationic helical scaffolds: rapid synthesis of diverse helquats via differential quaternization

  摘要：

  A protocol for rapid and highly modular assembly of a diverse set of helquats is described. From a common bis-isoquinoline precursor, two successive distinct pyridine-type nitrogen quaternizations followed by rhodium-catalyzed [2+2+2] cycloaddition afford non-symmetric [7]helquats. This route allows for straightforward molecular editing of cationic helical skeletons as exemplified by the synthesis of 15 different [5]-, [6]-, and [7]helquats. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.03.007

文献信息

• 2-(Substituted ethynyl)quinoline Derivatives as mGLUr5 Antagonists
  申请人：Korea Institute of Science and Technology

  公开号：US20140206876A1

  公开（公告）日：2014-07-24

  Provided is a 2-(substituted ethynyl)quinoline derivative having an mGluR5 antagonistic activity and pharmaceutically acceptable salts thereof. The compound of the present invention can be useful as a medicament for treating and preventing mGluR5 receptor-mediated diseases such as Alzheimer's disease, senile dementia, Parkinson's disease, L-DOPA-induced dyskinesia, Huntington's chorea, amyotrophic lateral sclerosis, multiple sclerosis, schizophrenia, anxiety disorder, depression, neuropathic pain, drug dependence, fragile X syndrome, autism, migraine and gastroesophageal reflux disease (GERD).

  提供的是一种具有mGluR5拮抗活性和其药用盐的2-(取代乙炔基)喹啉衍生物。本发明的化合物可用作治疗和预防mGluR5受体介导的疾病，如阿尔茨海默病、老年性痴呆、帕金森病、L-多巴诱导的运动障碍、亨廷顿舞蹈症、肌萎缩侧索硬化、多发性硬化、精神分裂症、焦虑症、抑郁症、神经病性疼痛、药物依赖、脆性X综合征、自闭症、偏头痛和胃食管反流病（GERD）的药物。
• Functionalisation of heteroaromatic N-oxides using organic superbase catalyst
  作者：Yuta Araki、Koji Kobayashi、Misato Yonemoto、Yoshinori Kondo

  DOI：10.1039/c0ob00740d

  日期：——

  Functionalisation of quinoline N-oxide was investigated using phophazene base as a catalyst; alkynylation and heteroarylation at 2-position were successfully achieved via nucleophilic addition–elimination process.

  使用膦嗪碱作为催化剂研究了喹啉N-氧化物的功能化；通过亲核加成-消除过程成功实现了2-位点的炔基化和杂芳基化。
• Isolation and structural characterization of a titanacyclopropane as key intermediate in the double aryl Grignard addition to 2-(arylethynyl)pyridine derivatives
  作者：Francesco Foschi、Torsten Roth、Markus Enders、Hubert Wadepohl、Eric Clot、Lutz H. Gade

  DOI：10.1039/c8cc00478a

  日期：——

  A titanacyclopropane species, which is a key reaction intermediate in the Ti(OiPr)4-mediated double aryl Grignard addition to 1,2-di(pyridin-2-yl)ethyne and related alkynes, was isolated and fully characterized. Based on this observation a one-pot synthesis of diarylated 1,2-di(pyridin-2-yl)ethanes and 2-(1,2,2-triarylvinyl)-pyridines was developed, including the tetraarylation of V-shaped 2,6-bis

  分离并充分表征了钛环丙烷物种，该物种是Ti（OiPr）4介导的双芳基格利雅（Grignard）除1,2-二（吡啶-2-基）乙炔和相关炔烃中的关键反应中间体。基于该观察结果，开发了一锅合成的二芳基化1,2-二（吡啶-2-基）乙烷和2-（1,2,2-三芳基乙烯基）-吡啶，包括V型2的四芳基化。 6-双（芳基乙炔基）吡啶。
• US8946431B2
  申请人：——

  公开号：US8946431B2

  公开（公告）日：2015-02-03
• Synthesis and biological evaluation of 2-(arylethynyl)quinoline derivatives as mGluR5 antagonists for the treatment of neuropathic pain
  作者：Myung-Hee Son、Ji Young Kim、Eun Jeong Lim、Du-Jong Baek、Kihang Choi、Jae Kyun Lee、Ae Nim Pae、Sun-Joon Min、Yong Seo Cho

  DOI：10.1016/j.bmcl.2012.12.056

  日期：2013.3

  We described here the synthesis and biological evaluation of mGluR5 antagonists containing a quinoline ring structure. Using intracellular calcium mobilization assay (FDSS assay), we identified compound 5n, showing high inhibitory activity against mGluR5. In addition, it was found that compound 5n has excellent stability profile. Finally, this compound exhibited favorable analgesic effects in spinal nerve ligation model of neuropathic pain, which is comparable to gabapentin. (c) 2012 Elsevier Ltd. All rights reserved.