N-methyl-3-(9-phenanthryl)propiolamide | 197231-99-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: N-methyl-3-(9-phenanthryl)propiolamide
• 英文别名: N-methyl-3-phenanthren-9-ylprop-2-ynamide
• CAS: 197231-99-5
• 化学式: C₁₈H₁₃NO
• 分子量: 259.307
• InChiKey: GLMITCWFMGDOMG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  间氟碘苯 、 N-methyl-3-(9-phenanthryl)propiolamide 在 甲酸 、 二乙胺 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 作用下， 以 乙酸乙酯 为溶剂， 反应 6.0h， 以83%的产率得到(Z)-3-(3-fluorophenyl)-N-methyl-3-(9-phenanthryl)-2-propenamide
  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 、 9-碘菲 在 copper(l) iodide 、 bis(triphenylphosphine) palladium (Il) acetate 、 三乙胺 作用下， 以 二甲基亚砜 为溶剂， 以82%的产率得到N-methyl-3-(9-phenanthryl)propiolamide
  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

• 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
• US5917038A
  申请人：——

  公开号：US5917038A

  公开（公告）日：1999-06-29
• US6069247A
  申请人：——

  公开号：US6069247A

  公开（公告）日：2000-05-30