7-ethynyl-2-methylquinoline | 1315248-51-1

• 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: 7-ethynyl-2-methylquinoline
• 英文别名: 7-Ethynyl-2-methyl-quinoline
• CAS: 1315248-51-1
• 化学式: C₁₂H₉N
• 分子量: 167.21
• InChiKey: KFYPOPYYJBPNTH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  7-ethynyl-2-methylquinoline 、 Langlois reagent 在 氧气 、 silver nitrate 作用下， 以 N-甲基吡咯烷酮 为溶剂， 反应 24.0h， 以76%的产率得到3,3,3-trifluoro-1-(2-methylquinolin-7-yl)propan-1-one
  参考文献：
  名称：

  Direct Synthesis of α-Trifluoromethyl Ketone from (Hetero)arylacetylene: Design, Intermediate Trapping, and Mechanistic Investigations

  摘要：

  Regioselective addition across the alkynes has been achieved in a silver-catalyzed protocol utilizing Langlois reagent (CF3SO2Na) and molecular O2 to access medicinally active α-trifluoromethyl ketone compounds. This method was successful in producing α-trifluoromethyl ketone in heterocyclic scaffolds, which are incompatible with earlier strategies. Experimental findings suggest a mechanism involving α-styrenyl radical intermediate and 1-methyl-2-pyrrolidinone (NMP) solvent, which leads to crystallographically characterized N-methylsuccinimide. Isotope labeling, kinetic studies, and intermediate trapping further helped to gain insight into this energy-demanding process.

  DOI：

  10.1021/ol502071g
• 作为产物：
  描述：

  7-溴-2-甲基喹啉 在 bis-triphenylphosphine-palladium(II) chloride 甲醇 、 copper(l) iodide 、 potassium carbonate 、 二乙胺 、 三苯基膦 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 7-ethynyl-2-methylquinoline
  参考文献：
  名称：

  [EN] MULTIPHOTON ACTIVABLE QUINOLINE DERIVATIVES, THEIR PREPARATION AND THEIR USES
  [FR] DÉRIVÉS DE QUINOLINE À ACTIVATION MULTIPHOTONIQUE, PRÉPARATION ET UTILISATIONS ASSOCIÉES

  摘要：

  本发明涉及对以下公式（I）响应的多光子可激活有机化合物。本发明还涉及一种合成本发明化合物的方法，一种包含至少一种本发明化合物的水溶液，以及它们的特定用途。本发明还涉及一种释放有机配体的方法，该方法涉及辐照根据本发明的化合物的步骤。

  公开号：

  WO2011086469A1

文献信息

• Multiphoton Activable Quinoline Derivatives, Their Preparation and Their Uses
  申请人：Dalko Peter

  公开号：US20130116281A1

  公开（公告）日：2013-05-09

  The present invention relates to multiphoton activable organic compounds responding to the following formula (I). The present invention also relates to a method of synthesizing the compounds of the invention, to an aqueous solution comprising at least one compound of the invention, and to their specific uses. The present invention also concerns a method of liberating organic ligands, said method involving the step of irradiating a compound according to the invention.

  本发明涉及响应以下式（I）的多光子可激活有机化合物。本发明还涉及一种合成本发明化合物的方法，涉及至少包含一种本发明化合物的水溶液，以及它们的特定用途。本发明还涉及一种释放有机配体的方法，该方法涉及照射本发明化合物的步骤。
• Multiphoton activable quinoline derivatives, their preparation and their uses
  申请人：Dalko Peter

  公开号：US08993767B2

  公开（公告）日：2015-03-31

  The present invention relates to multiphoton activable organic compounds responding to the following formula (I). The present invention also relates to a method of synthesizing the compounds of the invention, to an aqueous solution comprising at least one compound of the invention, and to their specific uses. The present invention also concerns a method of liberating organic ligands, said method involving the step of irradiating a compound according to the invention.

  本发明涉及响应以下式（I）的多光子可激活有机化合物。本发明还涉及一种合成本发明化合物的方法，一种包含本发明化合物的水溶液，以及它们的特定用途。本发明还涉及一种释放有机配体的方法，该方法涉及照射本发明化合物的步骤。
• MULTIPHOTON ACTIVABLE QUINOLINE DERIVATIVES, THEIR PREPARATION AND THEIR USES
  申请人：Centre National de la Recherche Scientifique

  公开号：EP2523937A1

  公开（公告）日：2012-11-21
• US8993767B2
  申请人：——

  公开号：US8993767B2

  公开（公告）日：2015-03-31
• Direct Synthesis of α-Trifluoromethyl Ketone from (Hetero)arylacetylene: Design, Intermediate Trapping, and Mechanistic Investigations
  作者：Arun Maji、Avijit Hazra、Debabrata Maiti

  DOI：10.1021/ol502071g

  日期：2014.9.5

  Regioselective addition across the alkynes has been achieved in a silver-catalyzed protocol utilizing Langlois reagent (CF3SO2Na) and molecular O2 to access medicinally active α-trifluoromethyl ketone compounds. This method was successful in producing α-trifluoromethyl ketone in heterocyclic scaffolds, which are incompatible with earlier strategies. Experimental findings suggest a mechanism involving α-styrenyl radical intermediate and 1-methyl-2-pyrrolidinone (NMP) solvent, which leads to crystallographically characterized N-methylsuccinimide. Isotope labeling, kinetic studies, and intermediate trapping further helped to gain insight into this energy-demanding process.