3-(3-fluorophenyl)-N-methylpropiolamide | 197231-94-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-(3-fluorophenyl)-N-methylpropiolamide
• 英文别名: 3-(3-fluorophenyl)-N-methylprop-2-ynamide
• CAS: 197231-94-0
• 化学式: C₁₀H₈FNO
• 分子量: 177.178
• InChiKey: JQEMHRRKJQCYPR-UHFFFAOYSA-N

物化性质

• 熔点：
  91-93 °C
• 密度：
  1.19±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(3-fluorophenyl)-N-methylpropiolamide 在 甲酸 、 bis(triphenylphosphine) palladium (Il) acetate 、 6-iodo-2-aminobenzimidazole 、 二乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 (Z)-3-(3-Fluoro-phenyl)-N-methyl-acrylamide
  参考文献：
  名称：

  Palladium-Catalyzed Hydroarylation of Propiolamides. A Regio- and Stereocontrolled Method for Preparing 3,3-Diarylacrylamides

  摘要：

  A general regio- and stereoselective synthesis of 3,3-diarylacrylamides is reported. Palladium-catalyzed coupling reactions of propiolamides with aryl halides provide arylpropiolamides. A subsequent hydroarylation reaction of these arylpropiolamides with aryl halides, catalytic palladium, an amine base, and formic acid in refluxing ethyl acetate provides 3,3-diarylacrylamides regio- and stereoselectively. The unique stereo- and regiocontrol is presumed to proceed through careful reaction parameters that allow intramolecular coordination of the propiolamide amide functionality to the transient palladium-alkyne complex. Palladium-catalyzed hydroarylation of propiolamides has not been studied; however, preliminary results from related systems suggest that regioselective addition can be achieved. The methodology as a synthesis tool is demonstrated in an efficient route to previously difficult-to-prepare potent, benzimidazole antiviral targets. In addition, the synthesis scope is explored where, by judicious choice of reaction sequence and aryl iodide, either the Z- or E-geometric isomer of a given pair of 3,3-diarylacrylamides is independently prepared.

  DOI：

  10.1021/jo980235h
• 作为产物：
  描述：

  N-methyl-2-propynamide 、 间氟碘苯 在 copper(l) iodide 、 bis(triphenylphosphine) palladium (Il) acetate 、 三乙胺 作用下， 以 乙酸乙酯 为溶剂， 以82%的产率得到3-(3-fluorophenyl)-N-methylpropiolamide
  参考文献：
  名称：

  Palladium-Catalyzed Hydroarylation of Propiolamides. A Regio- and Stereocontrolled Method for Preparing 3,3-Diarylacrylamides

  摘要：

  A general regio- and stereoselective synthesis of 3,3-diarylacrylamides is reported. Palladium-catalyzed coupling reactions of propiolamides with aryl halides provide arylpropiolamides. A subsequent hydroarylation reaction of these arylpropiolamides with aryl halides, catalytic palladium, an amine base, and formic acid in refluxing ethyl acetate provides 3,3-diarylacrylamides regio- and stereoselectively. The unique stereo- and regiocontrol is presumed to proceed through careful reaction parameters that allow intramolecular coordination of the propiolamide amide functionality to the transient palladium-alkyne complex. Palladium-catalyzed hydroarylation of propiolamides has not been studied; however, preliminary results from related systems suggest that regioselective addition can be achieved. The methodology as a synthesis tool is demonstrated in an efficient route to previously difficult-to-prepare potent, benzimidazole antiviral targets. In addition, the synthesis scope is explored where, by judicious choice of reaction sequence and aryl iodide, either the Z- or E-geometric isomer of a given pair of 3,3-diarylacrylamides is independently prepared.

  DOI：

  10.1021/jo980235h

文献信息

• [EN] PYRAZOLOPYRIDAZINE DERIVATIVES FOR THE TREATMENT OF HEPATITIS C<br/>[FR] DÉRIVÉS DE PYRAZOLOPYRIDAZINE POUR LE TRAITEMENT DE L'HÉPATITE C
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2011106340A1

  公开（公告）日：2011-09-01

  The disclosure provides compounds of formula (I), including their salts, as well as compositions and methods of using the compounds. The compounds have activity against hepatitis C virus (HCV) and may be useful in treating those infected with HCV.

  本公开提供了式(I)的化合物，包括其盐，以及使用这些化合物的组合物和方法。这些化合物对丙型肝炎病毒（HCV）具有活性，并可用于治疗HCV感染患者。
• Compounds for the Treatment of Hepatitis C
  申请人：Kadow John F.

  公开号：US20120046294A1

  公开（公告）日：2012-02-23

  The disclosure provides compounds of formula I, including their salts, as well as compositions and methods of using the compounds. The compounds have activity against hepatitis C virus (HCV) and may be useful in treating those infected with HCV.

  本披露提供了I式化合物，包括它们的盐，以及使用这些化合物的组合物和方法。这些化合物对丙型肝炎病毒（HCV）具有活性，可能对治疗感染了HCV的患者有用。
• A regio- and stereocontrolled method for preparing 3,3-diarylacrylamides
  作者：Lynne A. Hay、David Mitchell

  DOI：10.1016/s0040-4039(97)01528-1

  日期：1997.9

  Palladium-catalyzed hydroarylation of acetylenes provides regio- and stereodefined olefins. This methodology has been extended to arylpropiolamides where 3,3-diarylaclylamides are prepared stereospecifically. In an independent fashion, both the E- and Z-isomers were prepared by judicious choice of arylpropiolamide preparation and the palladium catalyzed hydroarylation reaction. (C) 1997 Elsevier Science Ltd.
• PROCESS OF PREPARING SUBSTITUTED ACRYLAMIDES
  申请人：ELI LILLY AND COMPANY

  公开号：EP0944581A1

  公开（公告）日：1999-09-29
• EP0944581A4
  申请人：——

  公开号：EP0944581A4

  公开（公告）日：2004-09-08