N-(quinolin-2-yl)acetamide | 50502-17-5

• 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
• 英文名称: N-(quinolin-2-yl)acetamide
• 英文别名: 2-acetamidoquinoline；2-Acetylaminoquinoline；N-quinolin-2-ylacetamide
• CAS: 50502-17-5
• 化学式: C₁₁H₁₀N₂O
• mdl: MFCD02690261
• 分子量: 186.213
• InChiKey: IOFUTXAOWYNJFY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 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：

  N-(quinolin-2-yl)acetamide 在 一水合肼 作用下， 以 乙醇 为溶剂， 生成 2-氨基喹啉
  参考文献：
  名称：

  Solvent-Dependent Cyclization of 2-Alkynylanilines and ClCF₂COONa for the Divergent Assembly of N-(Quinolin-2-yl)amides and Quinolin-2(1H)-ones

  摘要：

  DOI：

  10.1021/acs.orglett.1c01484
• 作为产物：
  描述：

  N-[2-(2-三甲基硅乙炔基)苯基]甲酰胺 在 吡啶 、 三光气 、 碳酸氢钠 、 copper dichloride 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 生成 N-(quinolin-2-yl)acetamide
  参考文献：
  名称：

  Solvent-Dependent Cyclization of 2-Alkynylanilines and ClCF₂COONa for the Divergent Assembly of N-(Quinolin-2-yl)amides and Quinolin-2(1H)-ones

  摘要：

  DOI：

  10.1021/acs.orglett.1c01484

文献信息

• TsOH·H₂O-mediated <i>N</i>-amidation of quinoline <i>N</i>-oxides: facile and regioselective synthesis of <i>N</i>-(quinolin-2-yl)amides
  作者：Xinghua Chen、Mei Peng、Hao Huang、Yangfan Zheng、Xiaojun Tao、Chunlian He、Yi Xiao

  DOI：10.1039/c8ob00862k

  日期：——

  An operationally simple method with 100% atom economy has been developed for the synthesis of various N-(quinolin-2-yl)amides via the TsOH·H2O-mediated N-amidation of quinoline N-oxides using inexpensive and commercially available nitriles as the amidation reagents. Mechanistic exploration suggested that the reaction probably proceeds through an acid-assisted 1,3-dipolar cycloaddition and an N–O bond

  已经开发出一种具有100％原子经济性的操作简单方法，用于使用廉价的市售腈通过TsOH·H 2 O介导的喹啉N-氧化物的N-酰胺化反应，合成各种N-（喹啉-2-基）酰胺。作为酰胺化试剂。机理探索表明，该反应可能是通过酸辅助的1,3-偶极环加成反应和N–O键裂解，然后进行脱氢芳构化过程来进行的。
• A novel three-component reaction of N-fluoropyridinium salts: a facile approach to imidazo[1,2-a]pyridines
  作者：Alexander S. Kiselyov

  DOI：10.1016/j.tetlet.2005.04.124

  日期：2005.6

  The reaction of N-fluoropyridinium triflate with isonitriles in acetonitrile and propionitrile in the presence of NaBH(OAc)3 led to the formation of the corresponding imidazo[1,2-a]pyridines in 44–73% yields. The proposed reaction mechanism involves the intermediate formation of a highly reactive carbene species and apparent reduction of the pyridinium intermediate with NaBH(OAc)3 to yield the targeted

  在NaBH（OAc）3存在下，三氟甲磺酸N-氟代吡啶鎓与乙腈和丙腈中的异腈反应，以44-73％的收率形成相应的咪唑并[1,2- a ]吡啶。拟议的反应机理涉及高反应性卡宾物质的中间形成和吡啶鎓中间体与NaBH（OAc）3的明显还原，从而生成目标杂环。
• [EN] SELECTIVE NEURONAL NITRIC OXIDE SYNTHASE INHIBITORS<br/>[FR] INHIBITEURS SÉLECTIFS DES OXYDE NITRIQUE SYNTHASES NEURONALES
  申请人：UNIV NORTHWESTERN

  公开号：WO2021081528A1

  公开（公告）日：2021-04-29

  Disclosed are 7-phenyl-2-aminoquinoline compounds that are shown to inhibit the biological activity of neuronal nitric oxide synthases (nNOSs). Also disclosed are pharmaceutical compositions comprising the compounds, and methods of using the compounds and pharmaceutical compositions for treating a subject in need thereof. Because the disclosed compounds are shown to inhibit the activity of neuronal nitric oxide synthases (nNOSs), the disclosed compounds and pharmaceutical compositions may be utilized in methods for treating a subject having or at risk for developing a disease or disorder that is associated with nNOS activity including neurological diseases and disorders.

  揭示了一种抑制神经一氧化氮合酶（nNOSs）生物活性的7-苯基-2-氨基喹啉化合物。还揭示了包含这些化合物的药物组合物，以及使用这些化合物和药物组合物治疗需要的主体的方法。由于这些揭示的化合物被证明可以抑制神经一氧化氮合酶（nNOSs）的活性，因此这些揭示的化合物和药物组合物可以用于治疗患有或有发展与nNOS活性相关的疾病或障碍的主体的方法，包括神经系统疾病和障碍。
• [EN] GLYCINE B ANTAGONISTS<br/>[FR] ANTAGONISTES DE LA GLYCINE B
  申请人：MERZ PHARMA GMBH & CO KGAA

  公开号：WO2010139483A1

  公开（公告）日：2010-12-09

  The invention relates to pyrazolopyrimidine derivatives as well as their pharmaceutically acceptable salts. The invention further relates to a process for the preparation of such compounds. The compounds of the invention are glycine B antagonists and are therefore useful for the control and prevention of various disorders, including neurological disorders.

  该发明涉及吡唑吡咪啉衍生物及其药用可接受的盐。该发明进一步涉及一种制备这种化合物的方法。该发明的化合物是甘氨酸B拮抗剂，因此可用于控制和预防各种疾病，包括神经系统疾病。
• Synthesis of enantiomerically pure amino-substituted fused bicyclic rings
  申请人：——

  公开号：US20030114679A1

  公开（公告）日：2003-06-19

  This invention describes various processes for synthesis and resolution of racemic amino-substituted fused bicyclic ring systems. One process utilizes selective hydrogenation of an amino-substituted fused bicyclic aromatic ring system. An alternative process prepares the racemic amino-substituted fused bicyclic ring system via nitrosation. In addition, the present invention describes the enzymatic resolution of a racemic mixture to produce the (R)- and (S)-forms of amino-substituted fused bicyclic rings as well as a racemization process to recycle the unpreferred enantioner. Further provided by this invention is an asymmetric synthesis of the (R)- or (S)-enantiomer of primary amino-substituted fused bicyclic ring systems.

  该发明描述了合成和分离外消旋氨基取代的融合双环环系统的各种过程。其中一种过程利用选择性氢化氨基取代的融合双环芳香环系统。另一种替代过程通过亚硝化制备外消旋氨基取代的融合双环环系统。此外，该发明描述了酶催化拆分外消旋混合物，以生产氨基取代的融合双环环的(R)-和(S)-形式，以及一个消旋过程来回收未优选的对映体。该发明还提供了外消旋氨基取代的融合双环环系统的(R)-或(S)-对映体的不对称合成。