3-(2-Phenylethynyl)pyridine-2-carbaldehyde | 222168-09-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 3-(2-Phenylethynyl)pyridine-2-carbaldehyde
• CAS: 222168-09-4
• 化学式: C₁₄H₉NO
• 分子量: 207.232
• InChiKey: NUJXEWVCCYMCHX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  30
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(2-Phenylethynyl)pyridine-2-carbaldehyde 在 manganese(IV) oxide 、 5%-palladium/activated carbon 、 氢气 作用下， 以 乙酸乙酯 、 苯 为溶剂， 20.0 ℃ 、1.38 MPa 条件下， 反应 14.0h， 生成 3-phenethyl-2-pyridinecarboxaldehyde
  参考文献：
  名称：

  Cyclizations of phenylethyl-substituted pyridinecarboxaldehydes

  摘要：

  Several phenylethyl-substituted pyridinecarboxaldehydes were prepared from 2-bromo-3-pyridinecarboxaldehyde and these substances are found to undergo cyclization reactions in acidic media. In the absence of added nucleophile, acid-promoted cyclization and oxidation (MnO2) provide an efficient route to 10,11-dihydro-5H-benzo[4,5]cyclohepta[1,2-b]pyridin-5-ones. Arene nucleophiles may also be added to the acidic mixture to provide good yields of triarylmethane products. Mechanisms are proposed involving dicationic superelectrophilic intermediates. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.01.004
• 作为产物：
  描述：

  2-溴-3-吡啶基三氟甲磺酸酯 在 bis-triphenylphosphine-palladium(II) chloride 、 lithium chloride 正丁基锂 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.67h， 生成 3-(2-Phenylethynyl)pyridine-2-carbaldehyde
  参考文献：
  名称：

  General Synthetic Method for Naphthyridines and Their N-Oxides Containing Isoquinolinic Nitrogen

  摘要：

  通过o-乙炔基吡啶甲醛与氨的反应，合成了含有异喹啉氮的取代萘啶。通过相应的肟，这些吡啶衍生物的N-氧化物也通过基本的环化反应得到合成。

  DOI：

  10.1055/s-1999-3379

文献信息

• Facile Assembly of Fused Isoquinolines by Gold(I)-Catalyzed Coupling-Cyclization Reactions between o-Alkynylbenzaldehydes and Aromatic Amines Containing Tethered Nucleophiles
  作者：Nitin T. Patil、Anil Kumar Mutyala、Pediredla G. V. V. Lakshmi、Penmatcha V. K. Raju、Balasubramanian Sridhar

  DOI：10.1002/ejoc.200901364

  日期：2010.4

  A gold(I)-catalyzed, operationally simple coupling-cyclization technique was developed for the synthesis of isoquinoline-fused polycyclic compounds. The reaction makes use of two coupling partners such as o-alkynylbenzaldehydes and aromatic amines having tethered nucleophiles. The reaction is easy to perform, broad in scope, and allows the generation of a number of biologically important heterocyclic

  开发了一种金 (I) 催化、操作简单的偶联环化技术，用于合成异喹啉稠合多环化合物。该反应利用两个偶联伙伴，例如邻炔基苯甲醛和具有系链亲核试剂的芳香胺。该反应易于进行，范围广泛，并允许从容易获得的起始材料中产生许多生物学上重要的杂环基序。讨论了反应机理。
• Transition‐Metal‐Free Reverse Reactivity of (2‐Alkynyl)‐Arylaldimines: Assembly of Functionalized Amino‐Indinones
  作者：Kapil Mohan Saini、Rakesh K. Saunthwal、Sushmita、Akhilesh K. Verma

  DOI：10.1002/chem.201904294

  日期：2020.1.22

  Transition‐metal‐free regioselective synthesis of functionalized amino‐indenones by the reaction of ortho‐alkynylaldehydes with a broad range of primary amines by intramolecular cyclization has been described. The designed reaction proceeds through KOH‐mediated Prins‐type cyclization and DMSO‐promoted oxidation of the cyclopent‐2‐en‐1‐one system. The proposed mechanism and role of solvent were well

  已经描述了通过分子内环化使邻炔基乙醛与多种伯胺反应而实现的无过渡金属区域选择性合成。设计的反应是通过KOH介导的Prins型环化反应和DMSO促进的环戊2环1环合一系统氧化而进行的。所提出的溶剂机理和作用得到了对照实验的很好支持。我们首次公开了（2-炔基）-芳基亚胺在超碱性体系中的逆反应性。
• Radical Cascade Cyclization: Reaction of 1,6-Enynes with Aryl Radicals by Electron Catalysis
  作者：Jun Xuan、Dario Gonzalez-Abradelo、Cristian Alejandro Strassert、Constantin-Gabriel Daniliuc、Armido Studer

  DOI：10.1002/ejoc.201601033

  日期：2016.10

  The radical cascade cyclization of various 1,6-enynes with aryl radicals by electron catalysis under metal-free reaction conditions was explored. Readily available anilines were used as radical precursors, and the reactions proceeded in the absence of any transition metal. These cascades comprise three C–C bond formations, which provide polycyclic structures with extended π-systems. The photophysical

  探索了在无金属反应条件下通过电子催化各种 1,6-烯炔与芳基自由基的自由基级联环化。容易获得的苯胺被用作自由基前体，反应在没有任何过渡金属的情况下进行。这些级联包含三个 C-C 键形成，提供具有扩展 π 系统的多环结构。研究了其中一些新化合物的光物理性质，并提出了合理的反应机制。
• Three-Component, One-Pot Sequential Synthesis of Tetracyclic Pyrido[2′,1′:2,3]imidazo[5,1-<i>a</i>]isoquinolinium Compounds as Potent Anticancer Agents
  作者：Huayong Zhou、Wei Wang、Oleg Khorev、Yongliang Zhang、Zehong Miao、Tao Meng、Jingkang Shen

  DOI：10.1002/ejoc.201200542

  日期：2012.10

  A new practical method for the synthesis of tetracyclic pyrido[2′,1′:2,3]imidazo[5,1-a]isoquinolinium compounds by a Yb(OTf)3/AgOTf-catalyzed (Tf = triflate) three-component domino reaction was developed. Significantly, the strategy presents a straightforward and efficient approach to constructing a series of compounds with potent cytotoxic activities.

  Yb(OTf)3/AgOTf-催化(Tf=三氟甲磺酸盐)三组分合成四环吡啶并[2',1':2,3]咪唑并[5,1-a]异喹啉化合物的实用新方法发生了多米诺骨牌反应。值得注意的是，该策略提供了一种直接有效的方法来构建一系列具有强细胞毒活性的化合物。
• [EN] ANALOGS OF 2-PRALIDOXIME AS ANTIDOTES AGAINST ORGANOPHOSPHORUS NERVE AGENTS<br/>[FR] ANALOGUES DE 2-PRALIDOXIME EN TANT QU'ANTIDOTES CONTRE DES AGENTS NEUROTOXIQUES ORGANOPHOSPHORÉS
  申请人：UNIV PITTSBURGH COMMONWEALTH SYS HIGHER EDUCATION

  公开号：WO2020027905A2

  公开（公告）日：2020-02-06

  Provided herein are compounds useful in treating exposure to an organophosphorus compound, such as a nerve agent, pesticide, or, generally, an acetylcholinesterase inhibitor, such as sarin. Compositions, e.g. pharmaceutical compositions or dosage forms, comprising the compounds also are provided herein. Methods of treating a patient exposed to a nerve agent, pesticide, or, generally, an acetylcholinesterase inhibitor, e.g., an organophosphorus compound, such as sarin, also are provided.