1-(pyridin-2-ylethynyl)isoquinoline | 1137276-01-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 1-(pyridin-2-ylethynyl)isoquinoline
• 英文别名: 1-(2-Pyridin-2-ylethynyl)isoquinoline
• CAS: 1137276-01-7
• 化学式: C₁₆H₁₀N₂
• 分子量: 230.269
• InChiKey: IGNIUZKDNPIERW-UHFFFAOYSA-N

物化性质

• 沸点：
  449.7±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)：
  3.1
• 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：

  1-(pyridin-2-ylethynyl)isoquinoline 、 pent-4-yn-1-yl trifluoromethanesulfonate 以 甲苯 为溶剂， 反应 25.0h， 以58%的产率得到2-(pent-3-ynyl)-1-(pyridin-2-ylethynyl)isoquinolinium 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 、 1-碘异喹啉 在 1,3-bis(N',N'-dimethyl-4-aminopyridinium)propane diiodide 、 9-羟基-萘嵌苯-1-酮 、 potassium tert-butylate 作用下， 以 二甲基亚砜 为溶剂， 以52 %的产率得到1-(pyridin-2-ylethynyl)isoquinoline
  参考文献：
  名称：

  奇数交替烃催化芳基卤化物与芳基炔烃之间的交叉偶联

  摘要：

  基于苯酚基单元的超还原奇数交替烃充当芳基卤化物和芳基炔之间交叉偶联的催化剂，合成丰富的内部炔烃库，无需任何外部刺激。该方案被扩展以在无过渡金属和无溶剂条件下完成 Sonogashira 型偶联。

  DOI：

  10.1002/chem.202400895

文献信息

• Helquats: A Facile, Modular, Scalable Route to Novel Helical Dications
  作者：Louis Adriaenssens、Lukáš Severa、Tereza Šálová、Ivana Císařová、Radek Pohl、David Šaman、Silvia V. Rocha、Nathaniel S. Finney、Lubomír Pospíšil、Petr Slavíček、Filip Teplý

  DOI：10.1002/chem.200801904

  日期：2009.1.19

  As easy as one, two, three: Relying on a facile [2+2+2]‐cycloisomerization strategy, we have developed a robust three‐step synthetic entry into a novel family of helical extended diquats (helquats). The key metal‐catalyzed step proceeds in water under aerobic conditions to produce a water‐soluble, blue fluorophore (picture; TfO=triflate). The electrochemical manifold of the parent helquat features

  像一，二，三一样容易：依靠一种简便的[2 + 2 + 2]-环异构化策略，我们已经开发出了一种稳健的三步合成方法，可以进入一个新颖的螺旋扩展二枯草（helquats）系列。关键的金属催化步骤在有氧条件下在水中进行，以生成水溶性蓝色荧光团（图片； TfO =三氟甲磺酸盐）。原始头盔的电化学歧管具有两个可逆的单电子还原步骤。
• [EN] SUBSTITUTED ACETYLENE DERIVATIVES AND THEIR USE AS POSITIVE ALLOSTERIC MODULATORS OF MGLUR4<br/>[FR] DÉRIVÉS D'ACÉTYLÈNE SUBSTITUÉS ET LEUR UTILISATION À TITRE DE MODULATEURS ALLOSTÉRIQUES POSITIFS DU MGLUR4
  申请人：MERCK PATENT GMBH

  公开号：WO2014121883A1

  公开（公告）日：2014-08-14

  The present invention relates to novel acetylene derivatives as positive allosteric modulators for modulating metabotropic glutamate receptor subtype 4 (mGluR4) and/or altering glutamate level or glutamatergic signalling.

  本发明涉及作为调节代谢型谷氨酸受体亚型4（mGluR4）的正向变构调节剂以及/或改变谷氨酸水平或谷氨酸信号传导的新型乙炔衍生物。
• Substituted Acetylene Derivatives and their Use as Positive Allosteric Modulators of mGluR4
  申请人：MERCK PATENT GMBH

  公开号：US20150376182A1

  公开（公告）日：2015-12-31

  The present invention relates to novel acetylene derivatives as positive allosteric modulators for modulating metabotropic glutamate receptor subtype 4 (mGluR4) and/or altering glutamate level or glutamatergic signalling.

  本发明涉及新型乙炔衍生物，作为正向变构调节剂，用于调节代谢型谷氨酸受体亚型4（mGluR4）和/或改变谷氨酸水平或谷氨酸信号传导。
• US9879004B2
  申请人：——

  公开号：US9879004B2

  公开（公告）日：2018-01-30
• [EN] NOVEL HELQUATS, THEIR PRECURSORS AND METHOD OF PREPARATION THEREOF<br/>[FR] NOUVEAUX HELQUATS, LEURS PRÉCURSEURS ET PROCÉDÉ DE PRÉPARATION ASSOCIÉ
  申请人：USTAV ORGANICKE CHEMIE A BIOCH

  公开号：WO2010118711A2

  公开（公告）日：2010-10-21

  Described are new helquats of general.formula I, their precursors of general formula II and III and methods of their preparation from compound of. general formula IV, where symbols S12, S1`2`, T23, T2`3` , R1 , R 2, X- have the meaning defined in description and claims. According to this invention it is possible e.g. from one non-symmetric compound of general formula IV (tether S1,2 is different from tether S1`2`) and 10 different alkylation agents to prepare 100 various helquats of general1, formula I and 90 various helquats without repetition of the alkylation agent. From symmetric compound of general formula IV (tether S1,2 is the same as tether S1`2` ) and 10 different alkylation agents it is possible to prepare 55 various helquats of general formula I and 45 various helquats without repetition of the alkylation agent.