4,5-dichloro-N-[3-(3-cyano-4-fluorophenyl)prop-2-ynyl]-N-[(2,4-dimethoxyphenyl)methyl]-1H-pyrrole-2-carboxamide | 959771-83-6

• 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: 4,5-dichloro-N-[3-(3-cyano-4-fluorophenyl)prop-2-ynyl]-N-[(2,4-dimethoxyphenyl)methyl]-1H-pyrrole-2-carboxamide
• CAS: 959771-83-6
• 化学式: C₂₄H₁₈Cl₂FN₃O₃
• 分子量: 486.33
• InChiKey: QFTYYMDTLLXWIR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  33
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  78.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4,5-dichloro-N-[3-(3-cyano-4-fluorophenyl)prop-2-ynyl]-N-[(2,4-dimethoxyphenyl)methyl]-1H-pyrrole-2-carboxamide 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三异丙基硅烷 、 三氟乙酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.33h， 生成 5-[(6,7-dichloro-1-oxo-1,2-dihydropyrrolo[1,2-a]pyrazin-4-yl)methyl]-2-fluorobenzonitrile
  参考文献：
  名称：

  A novel base-mediated intramolecular hydroamination to build fused heteroaryl pyrazinones

  摘要：

  Functionalized fused heteroaryl pyrazinones were built up through a novel DBU-catalyzed intramolecular hydroamination reaction of aryl(prop-2-yn-1-yl)-1H-heteroaryl-2-carboxamides. The nucleophilic addition afforded three isomers; two with an exo-cyclic double bond [cis (Z), trans (E)], and a third one with an endo-cyclic double bond. After the carboxamide deprotection, isomerization of the mixture under acidic conditions resulted in a unique isomer. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.10.116
• 作为产物：
  描述：

  5-(3-(2,4-dimethoxybenzylamino)prop-1-ynyl)-2-fluorobenzonitrile 、 4,5-二氯-1H-吡咯-2-羧酸 在 三乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以50%的产率得到4,5-dichloro-N-[3-(3-cyano-4-fluorophenyl)prop-2-ynyl]-N-[(2,4-dimethoxyphenyl)methyl]-1H-pyrrole-2-carboxamide
  参考文献：
  名称：

  A novel base-mediated intramolecular hydroamination to build fused heteroaryl pyrazinones

  摘要：

  Functionalized fused heteroaryl pyrazinones were built up through a novel DBU-catalyzed intramolecular hydroamination reaction of aryl(prop-2-yn-1-yl)-1H-heteroaryl-2-carboxamides. The nucleophilic addition afforded three isomers; two with an exo-cyclic double bond [cis (Z), trans (E)], and a third one with an endo-cyclic double bond. After the carboxamide deprotection, isomerization of the mixture under acidic conditions resulted in a unique isomer. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.10.116

文献信息

• A novel base-mediated intramolecular hydroamination to build fused heteroaryl pyrazinones
  作者：Laura Llauger、Costanza Bergami、Olaf D. Kinzel、Samuele Lillini、Giovanna Pescatore、Caterina Torrisi、Philip Jones

  DOI：10.1016/j.tetlet.2008.10.116

  日期：2009.1

  Functionalized fused heteroaryl pyrazinones were built up through a novel DBU-catalyzed intramolecular hydroamination reaction of aryl(prop-2-yn-1-yl)-1H-heteroaryl-2-carboxamides. The nucleophilic addition afforded three isomers; two with an exo-cyclic double bond [cis (Z), trans (E)], and a third one with an endo-cyclic double bond. After the carboxamide deprotection, isomerization of the mixture under acidic conditions resulted in a unique isomer. (C) 2008 Elsevier Ltd. All rights reserved.